How to Say Hurray for Lingerie as a Person of Trans* Experience

Sep 6, 2017 | Being Your True Self, Hurray for Lingerie | 12 comments

In April of 2017 I made a big deliberate choice. It was moments before the taping of my appearance on The Rachael Ray show, and in front of Rachael, a live audience, and 2 million+ people, I said that “I have fit thousands of people for bras.” Seems simple, right. After all, it’s true. I have fit so many people for bras in my 12+ year in the lingerie industry and as a bra fitter that I’ve lost count. But when I say that I’ve helped thousands of people in the bra fitting room, I mean people. And people come in all different types. People vary by age, size, shape, ability, color… and gender. I used to say that I’ve fit women for bras – and that is true! I love fitting women. But I have also helped men. And people that do not fit into our binary standards of male and female, man or woman. And saying that for the first time in such a big way felt right.

As a cisgender female {that means that my personal sense of gender identity corresponds with my birth sex} I’ve never questioned my womanhood. I was born as a female by sex and assigned girl as my gender, and I have always felt that I was a woman, through and through. It wasn’t even until I started as a bra fitter, in my late teens and early 20’s that I first witnessed anyone who may feel otherwise about themselves. And it wasn’t until I was being interviewed for an article on a very inclusive site that I was actually asked “what pronoun would you like for us to use for you? How do you identify?” It wasn’t that the writer questioned my gender identity, or that I did. I present as a woman in the way I walk, dress, talk, and act. My actions follow most of society’s current terms and conditions for being a woman (I say most, because not all) – and she saw that. What was so eye opening was the fact that I had never even had to think about my gender identity being questioned. And this, friends, is not a privilege that everyone has.

Gender and Undergarments

Gender is a hot topic right now. There is a new societal emphasis on conversing about things like gender identity, transgender, gender presentation, genderqueer, gender-variant, gender non-conforming, gender roles, gender vs. sex, and other important aspects of gender. Our societal collective is opening up to the fact that not all things and people fit into our binary (as in, just two exist) gender norms. And, we’re even stretching and opening up our views on what the norms for each gender can look like. It’s exciting. It’s wobbly and wonky as we learn our way together as a society. And it’s about dang time!

{PS: I understand that keeping track of all of these terms and experiences can get overwhelming, right? Helpful tip: This Transgender 101 article outlines a lot of the basics. Please take a moment to lovingly educate yourself. And keep an eye out for other helpful articles and information along the way. I’m still learning myself and have leaned on those in the community to help me find the right language and appropriate words.}

Today, I want to discuss something specific: transgender. And I’m going to get even more specific: being transgender and shopping for undergarments. Because, undergarments are my jam, and they offer a very real opportunity to explore gender identity. Bras and underwear clothe two of our most sacred human parts, and parts in which we often associate gender norms.

As I mentioned, I have fit thousands of people for bras and undergarments since 2005 in NYC. And of those, a handful were of trans* experience. That I even knew of. Some clients would openly, or reluctantly, or nervously tell me. Others appeared to be transitioning and I felt no need to point it out, but used my educated guess to help advise them on the best products for their body and needs. And others, quite frankly, I could have helped and never known. As a bra fitter, it’s not entirely necessary for me to know. A person’s gender is not my business. But I say “entirely”, because there are some instances when it’s super helpful to know. For instance, if the person is just starting to transition and their bust may be fluctuating quite a bit, this information could help me determine what size to suggest. Or, if they are just starting to wear bras in their 30’s, and may need a more basic understanding of how to wear them (I actually usually go over this anyway with everyone, regardless of age). Or if they’d like to wear a push up or prosthesis, a waist-cincher or padded underwear, or other undergarment to achieve a specific (oftentimes one influenced by gender) silhouette.

The tricky thing is, however, that it may not always feel safe to reveal yourself in such a way. I understand. I remember one lovely client entering the tiny fitting room with me in a great deal of fear. They were breathing deep, their eyes darting back and forth, as they assessed if they were in danger of being judged, kicked out of the boutique, or worse. For all I knew, this was their first time bra shopping ever. Or they had gone for one before and been met with refusal of business and prejudice. In the moment, I tried my best to be cool and pretend that nothing was different in order to make them feel comfortable. Clearly, though, this person was different than most of my clients. Because they were transitioning, they had different needs than the woman in the next fitting room. And being aware of and sensitive to that, and understanding the specific needs really helps me serve this lovely person with much more care. Instead, as a young person, I felt the twinge of worry about what the woman in the next room would think, and didn’t want to make her uncomfortable. We were on the Upper East Side of Manhattan, an area known for having an older, richer, more conservative clientele. I made all sorts of assumptions about her, about the person in my fitting room, and about whose comfort really mattered most. I thought I kept everyone’s needs and desires in mind and handled it well at the time. In fact, everyone left quite happy! And now, I realize there was probably even more room for love in that small fitting room. Gosh, I’m so thankful to learn more and more all the time.

You see, going in for a bra fitting or lingerie shopping is a revealing and intimate experience. I use my knowledge and expertise as a tool to help people say hurray inside, outside, and underneath – and it’s a tool that I use with much sacredness. And not every bra fitter, or bra salesperson, or lingerie boutique owner does so. Or, quite frankly, has helped a person of trans* experience. I try to be compassionate for that bra fitter, because I was her once as well.

I’m not here to tell you what to think, how to feel, who to be – when it comes to yourself or relating to others. I’m here to shine a light on the very real experiences that some of our fellow human beings are having. I’ve felt a calling for a long time to show up and step up for the trans* community. Hurray Kimmay is all about saying hurray on the inside, outside, and underneath. And that means for everyone. A lot of what I share here on my site comes from my own personal experience, which is that of a married, cisgender, heterosexual, white passing Latina of mixed heritage. And I know it’s important to share the experiences of others. I do so in campaigns like #MoreThanMyNumbers {shameless and super proud shout out}, or by including reader write-ins in some of my Pros & Cons articles, and more. And providing a platform and a voice for those who may not have a way to share their experience is a big hurray.

Meeting Nicki

So imagine my delight when a popular online website said they wanted to shine a light on transgender undergarment needs and frustrations in a Facebook Live with me. I was thrilled! But this opportunity seemed to be doomed. As we were preparing to shoot it earlier this year, it got pushed back several months. Then, as the new date approached, I started reaching out in my community and online looking for people of trans* experience to share their thoughts about their underwear on camera for everyone to see… and kept hitting a wall. With good reason, there was a reluctancy to show their bodies and share their vulnerabilities and even sexuality in a seemingly casual conversation. Or they didn’t live in the NYC area. Or they were unavailable. And while the online publication is well known for their forward thinking and inclusive articles {there’s no need to speculate on why I’m not including their name. I just don’t want their name to be the focus of this article} I also got the sense that a few may have felt like their experience was suddenly trendy and they were being exploited. No one said this to me. And I could be making it up. But it was certainly on my mind, as it was important to me that this not be an exploitative scenario. I was determined to move forward and share the narrative with compassion, helpful guidance, and love.

So, within days of the shoot, I was quite pleased to be introduced to a young woman of trans* experience: Nicki. Nicki went to college with my younger brother, and he introduced us. What started as an email exchange back and forth, and then a Skype call, blossomed into something much bigger. I asked if I could interview her for the Facebook Live opportunity and she revealed to me her story of transitioning, her hopes and fears, trials and triumphs, and her dream to become the first trans* Victoria’s Secret Angel. I assumed that she wouldn’t fly in from Florida to NYC for this short Facebook Live event, but she jumped at the chance. I cautioned Nicki that she shouldn’t act too swiftly, because the shoot was not confirmed and we hadn’t hammered out details. But something about our relationship, our goals and message, and our timing felt so aligned. After some back and forth with the publication and no real details, I finally told her that while things were not really finalized, that I wanted to work with her anyway. We both agreed that we KNEW we should work together somehow. She booked the ticket. And within hours, I got a “sorry we have to put this on hold” email from the publication. 

Making Lemonade Out of Lemons

I called Nicki to tell her that the Facebook Live shoot with the online publication had been cancelled and we were both disappointed. Not because we weren’t going to be on some fancy publication’s Facebook page, but because it felt like our chance to share our message in a big way was lost. So. I used a mantra my coach taught me and shared it with Nicki: “What if this is happening FOR us, and not TO us?” We decided to move forward with her trip to New York City. And, I told Nicki, “Let’s make some lemonade out of these lemons. Like, really good lemonade.” We decided to create something (this thing you’re reading now) for my site, including a photo shoot and interviews. Plus, it was Pride weekend in NYC. So I created an itinerary (I’m not kidding, a very detailed itinerary) and reached out to people in my community and in the trans* community to create this weekend.

One such person was my friend and colleague, Laura Boyd of the boudoir photography studio, Own Your Sexy. I told her about Nicki, I told her what had happened, and I told her about Nicki’s dreams to be a Victoria’s Secret Angel. I also told her that I had already sent out requests to a few brands and companies, but with such short notice, had no luck securing funds or a paying sponsor. Funds would all be coming out of my pocket. Laura, angel that SHE is, contributed the photo shoot and images of Nicki to us as a gift. Her support of my mission to help people say hurray, and of the LGBTQIA+ community itself, can not be overstated.

Five Days to Say Hurray

It feels impossible to do a quick recap of our adventures, the bonding, and the learning that we both did during this time – but it feels important to at least try. So below is a as-brief-as-possible timeline of our activities and some quick memories of Nicki’s trip to NYC with me. I have so many photos and lots of video, and for brevity’s sake (trust me, I’m trying) I’m just giving you the facts.

Read about our 5 Days of Hurray

Day 1: Girl’s night with my friends on my office terrace. I finally meet Nicki in person and introduce her to some of my friends and we have deep, beautiful conversations in the warm air.

A few memories, in short:

  • Seeing this beautiful woman in person for the first time took my breath away
  • Introducing her to my friends for “girl’s night” felt totally perfect and we had such a fun time. Her mom later told me that meant to a lot to her, and I was so happy to hear it.
  • Nicki was candid and open, never hiding her transition experience and always answering questions, and yet never making it the sole focus. Such a beautiful balance.
  • Conversations that dance back and forth between deep, poignant topics and silly, giggly chats.

Day 2: Trans* March. Nicki, her mother, and I meet up in Washington Square Park to attend the 13th Annual Trans Day of Action March then get lunch together.

A few memories, in short:

  • Witness the trans* community and supporters rally, especially trans* POC. It was filled with a lot of education, support, and sometimes anger.
  • Having beautiful conversations with Nicki’s mother. She is one of the sweetest, kindest, most gentle women I’ve ever met and watching her march alongside her daughter was truly beautiful.
  • A young trans* femme person came up to Nicki in the crowd and said: “Oh my gawd, you are so beautiful!” Nicki was so touched, we went over and took photos with them and introduced ourselves. I could tell that she felt included, invited, and seen by her community.

Day 3: Lingerie shopping and bra fitting day! Nicki and I went shopping for lingerie to pick out outfits for her shoot, and for her to take home. We spent hours trying on gorgeous lingerie all over Manhattan.

A few memories, in short:

  • Introducing Nicki to some of the most fabulous lingerie brands, and hearing her requests.
  • Watching her absolutely light up when we went into Victoria’s Secret on Fifth Ave
  • When Nicki got asked if she was a Victoria’s Secret Angel in the store! (More below)
  • Jetting around Manhattan together, tired, hot, and yet so filled with hurray

Day 4: NYC Pride Parade and Wild Woman Circle. Nicki and I met up with some of my friends for the NYC Pride Parade, supporting the LGBTQIA+ community in Manhattan. The group left the parade early to go to my new moon circle with The Wild Woman Project where we set intentions and shared our deepest feelings.

A few memories, in short:

  • Watching Nicki pick out specific people’s faces on the print outs honoring the victim’s of the Orlando shooting. Nicki used to work at Pulse nightclub and knew several of those there that night, and the victims.
  • Feeling a sense of community and saying out loud: “whenever you feel like you’re unloved, remember all these people here today who support and love you.”
  • One of my friends whispered, “wait… is she transgender? I had no idea.”
  • Nicki thanked me for not introducing her as “her trans* friend”, but simply as, “My friend, Nicki”.
  • The welcoming that Nicki received into the women’s circle as just that, a woman. Because that is who she is.

Day 5: Boudoir photoshoot at the Own Your Sexy Studios and video interview. The day was finally here! Nicki did her own hair and makeup (she looked amazing) and Laura and I got to work. It was a short shoot, and together we made magic!

A few memories, in short:

  • Watching Nicki in her element, totally crushing it
  • Seeing Nicki see the proofs on the camera and loving what she sees
  • Back at my office, interviewing Nicki – and then her mom! – about the experience, and what’s next.
  • Hearing Laura say, when Nicki walked into the studio: “Oh my goodness, she LOOKS like an Angel!”

Five days of hurray. Not everything went as planned and I was actually a little bit of a train wreck. Quite frankly, I had overbooked myself, and was pushing so hard to squeeze that lemon juice to make lemonade that I had to keep reminding myself to slow down and enjoy everything. After all, everything was happening FOR us, not TO us.

Kimmay and nicki hugging circle

Why Victoria’s Secret

So, I want to point out something about Victoria’s Secret. At first, when I heard Nicki say that her goal was to be a Victoria’s Secret Angel, I recoiled. I believe that Victoria’s Secret has a purpose in the lingerie world, for sure. But I had several reservations about Nicki’s aspirations for working with them. And as a protective older sister, I laid them out. 1. VS is so mainstream, and often mainstream companies do a great disservice to those who do not fit into their narrow size range or commercial stereotypes. 2. They are traditionally non inclusive of gender non conforming people or their needs. 3. Quite frankly, I’m not always impressed with their products or quality. 4. The way they market to and talk to women can be quite damaging. 5. There are so many amazing, inclusive, lingerie brands who are doing great work to be inclusive and mindful and open hearted. I wanted Nicki to try those brands and fall in love with them.

So when we went shopping together, I introduced Nicki to some of my favorite lingerie brands. Brands that I thought would wow her with their sophistication, open mindedness, and more. And while she liked them, she still wanted a different hurray. So, we strode over to the big Victoria’s Secret on Fifth Avenue. Right away, Nicki’s attitude changed. She lit up. It was like watching a kid in a candy shop! At 23 years old and spending most of her life in Florida, Victoria’s Secret was what she knew. Just like most young women her age. And when we ventured upstairs to the VS runway museum (legit, there’s a museum of costumes and lingerie up there), I was witness to a very special exchange.

While I was taking some snapshots of Nicki against a wall with wings as a background, a young woman and her family shyly strode over and asked:

“…Are you a Victoria’s Secret Angel?”

Nicki paused, for like a second, and I interjected: “Not yet, but she will be.”

The family of three lit up. “May we take a picture with you?” they asked.

“Sure!” said Nicki, graciously.

I was in awe watching their young daughter, sweet and awkward in her early teen years, looking up to Nicki. I saw her parents embrace Nicki and wish her luck on her road to the Angel runway. I saw them see beauty, and work ethic, and openness, and Nicki herself. I did not see them see “oh, that’s a trans* woman”. And come to find out – this was not the first time Nicki had been mistaken for an Angel.

Suddenly, Nicki’s goal to work with Victoria’s Secret made sense to me.

You see, when it comes down to it, we need more transgender models in mainstream lingerie and undergarment ads and companies because that’s what people know. It’s what they understand. Seeing someone like Nicki in the mainstream lingerie world can help them bridge the gap between where they stand now and what they currently understand, and the realities that exist for others outside of the binary ideas of man and woman. As Nicki said to me, “people fear what they can’t see”. To a majority of people in our country (and certainly beyond), a non-binary person, or a person of trans* experience is unknown to them. They can’t understand what it means. They may not see this type of gender identity in their neighbor, brother, co-worker, or dear friend. And they make up all sorts of assumptions and stories using misguided and fearful information.

So, I would like for you to see and witness these beautiful people of trans* experience. I hope what you see, read, and witness will help ease any fears or misunderstandings you may have. I hope that you can open your heart to see – truly see – these beautiful people for who they are: people. Their stories are below. One such transwoman is Pooya. In her revealing article with Advocate, she explains that she felt lost and fell into despair during her transition because she “had never met a trans person — never even personally seen a trans person, except as some twisted depiction in a Hollywood movie. … There was no outside voice: no articles, no television show.” As an actress, her work in mainstream entertainment could also help bridge the gap.

Something that came up in both my conversation with Nicki and in the Advocate article with Pooya was their admittance that not every person who transitions has an easy time visibly “passing” as their gender. Or, at least as easy of a time as they have had. This is true for most at the start of transition, and for many even after a lengthy transition process. Not to mention, it often costs a great deal of money to “successfully pass”, as some have put it. And not passing as your gender can be tremendously difficult for many reasons – those you can imagine and perhaps more that you can not. In Nicki and Pooya’s cases, they not only pass as women, they are quite beautiful by society’s standards. This makes them uniquely qualified to reach a group of people that perhaps their trans* brothers and sisters may not be able to with as much ease. This kind of privilege is not lost on them. Even just showing up and volunteering to share their stories with us here is a brave and vulnerable thing to do. And I know they are already making big waves, and are ready to make even bigger waves soon.

Here are some big waves. Take a look at Nicki’s photoshoot.

All images: Produced by Kimmay Caldwell of Hurray Media for Hurray Kimmay. Photography by Laura Boyd of Own Your Sexy. Model, Nicki Vrotsos.

{Psst! These beautiful pieces were provided by Maison Close and Playout. Thank you to these brands and amazing photographer Laura Boyd of Own Your Sexy. More info on these companies below.}



How to Say Hurray for Lingerie as a person of Trans* experience

Learn the Basics 

This site and several other websites around the web are filled with wonderful information on undergarments and bra fitting. Here are a few places to start:

  • Read my article for LiveAbout on The Best Lingerie for the Transgender Community – includes links to some of the best brands and products you may want to try (for both trans* masculine and feminine needs) and specific style advice
  • Bra Size: Take your measurements and learn your bra size starting points – bra fitting and sizing can be confusing, so use this as a great place to start so you’re not totally guessing when trying on bras. Sometimes this simple first step can lead to a great awareness about bra sizes and what may fit you best.
  • Fit Tips: Learn how to tell if your bra fits with my Top 5 Bra Fit Tips PDF, printable checklist, and video. Getting a good fit is really the biggest key to feeling comfortable and confident in your undergarments.
  • Fundamentals: Learn one of the fundamentals of bra sizing: sister sizing. This bra fitting tip can be a lifesaver when it comes to determining how to adjust your size when looking for the best fit.
  • Styles: Explore more styles and which may work best for you in my Underneath Resources pages.

Get to Know your Body 

Your body is unique. Throughout your life it will change – especially certain physical aspects during transition. And even after a transition period, our bodies still change due to weight gain or loss, hormone fluctuations, age, stress, and more. Get to know yours and what it looks like, how it feels when you wear certain things, and what support and comfort it craves.

That means taking your measurements and calculating your bra size starting points (see above). It also means knowing that your body may have different needs than what the undergarments you find in mainstream shops can provide. Knowing your body and what it needs to feel and look its best during each step of your transition, and each phase of life is crucial when deciding where to shop and with whom to shop. Being informed about your own needs can helps others help you. For example, if you have had breast augmentation surgery, what specific bra needs may you have? Perhaps they’re firmer or set far apart and a bralette may be a better fit than an underwire, molded bra. Or if you have not had augmentation and want the appearance of a fuller bust, what can help you? Perhaps a push up bra, or a bra with inserts could be work. These are all things to explore and to share. Speak up and tell your fitter, tell the brands, tell the world. We need some massive changes made, pronto, and when you speak up, it helps brands know what to create and how to help you.

Plus, getting to know and love your body is one of the most amazing journeys of life. I’m still learning how to be my body’s best friend. Like with any deep relationship, we’ve had our ups and downs. And continuously working toward a more loving and compassionate relationship opens up opportunities to love other parts of yourself. And eventually, that love inside yourself helps you to love and understand other people, too. It’s a ripple effect that our entire world can benefit from. Hurray to that.


Discover What Makes YOU Say Hurray 

I and fashion magazines and your best friend and your partner and that advertisement can each suggest what to wear. And when it comes down to it, it’s YOUR body, your life, your journey. Exploring your desires and what you love is a process. It takes some time and letting go of other people’s expectations and your own judgements to find what really makes you say hurray. And by hurray, I mean the kind of hurray that comes from knowing that what you are putting on your body, and how you are relating to it brings deep, personal pleasure that spreads from the inside, to underneath, and out.

Undergarments are such a wonderful place to start. Often, they can be worn underneath clothing, which means you can choose to wear them just for yourself. That means you can explore how they make you feel throughout the day without having to show or present them to anyone else. This can help inform what identity you want to then share with the world. It’s all learning. It’s all a pathway to owning your whole self, and deciding when and how to share it with others.


Understand That Your Are Loved, and Lovable

Many of the trans* interviewees discussed feeling alone, misunderstood, and unsupported when shopping for undergarments. Some even relayed stories of feeling threatened or ignored. I want you to know that I see you. You are seen, and heard, and loved, and cared for. And not just by me. There are people everywhere who share your experience, or who are learning to understand it, and who support you, and who love you. Not to mention, you were divinely created and are loved from above. Just sayin’.

So when you’re struggling to feel loved and lovable, I encourage you to have a way to remember that you are. Keep a mantra in your pocket. Wear a necklace that reminds you love is all around. Connect with a friend or a member of your community to remember that you are not alone. And certainly, adorn yourself with beautiful bras and lingerie to remind yourself that you are beautiful. Even if no one else sees it, you know it’s true.

Get to know and love yourself. Because it’s hard to receive this kind of love and support from others, or to even feel that it’s there, if you are having trouble receiving love from yourself. We all struggle with self doubt, and the trans* community has so much outside pressure and prejudice that feeds those old stories of “I’m not good enough,” or “something is wrong with me”, or “I’m not beautiful”. So take some time to practice forgiving yourself for the misunderstanding that those stories are true. Because they are not. What is true is that you are loved and lovable, just as you are.


Of course, my favorite ways to say hurray is with a bra fitting and coaching session! Find a local bra fitter, or I invite you to talk with me about my services.

Read more about what it’s like to shop for undergarments as a person of trans* experience below!


Nicki Vrotsos is an aspiring lingerie model, and a woman of trans* experience. Find her on Instagram, SnapChat, and watch this amazing video.

Read more about Nicki

How do you identify? Are you trans, non-binary, etc? Can you explain a little bit about what that means for someone who may not know? 

I often identify simply as a woman but there are, however, many onlookers who seem to be unsatisfied by that because often in their words I “just can’t stop being trans*”—or some wording along those lines. I most certainly cherish my trans* experience and wouldn’t have it any other way but I don’t believe that I have to fit my entire existence into a box labeled gender. With that enlightenment in mind, I am a person first a foremost and then a woman of trans* experience following suit. It must be understood that “transgender” or “trans*” has the ability to not only be a specific identity but also an umbrella term for a community as a whole. To be transgender you are not limited to being a transgender boy/man or transgender girl/woman because in actuality there are hundreds of non cisgender genders which follow under the “Transgender Umbrella” and at the end of the day, that is what “transgender” means—to not be cisgender [when based on sociological norms your gender and outward anatomical sex presentation (i.e. genitalia) “line up” (i.e. boy with a penis or girl with a vagina)]. According to TSER (Trans Student Educational Resources) non binary refers to the “preferred umbrella term for all genders other than female/male or woman/man, used as an adjective (e.g. Jesse is a nonbinary person). Not all nonbinary people identify as trans and not all trans people identify as nonbinary. Sometimes (and increasingly), nonbinary can be used to describe the aesthetic/presentation/expression of a cisgender or transgender person.”

How do you think your (or in general) gender identity relates to your undergarments? 

I think undergarments have an ability to help shape someone’s gender especially if a new and different gender is being explored. It can be an incredibly validating way to feel more comfortable in your skin throughout all stages of transition. In my personal experience, having reason to need a bra was one of the most reassuring moments for me early on in my medical transition.

Lingerie has allowed me to adorn my body with not only pride but my newfound love for it, in its truest of forms. The journey of self love has been so empowering I wish one day that I’m able to share that as the first transgender Victorias Secret Angel. I can’t imagine a greater testament to my community, that I would be able to provide, as proof that glass ceilings are able to be broken through and living authentically as your true self is nothing but a beautiful journey to success.

What’s it like shopping for undergarments? Do you feel like you have to choose a section based on gender online or at a shop?

Undergarments have always been predominately segregated based on outward anatomical genitalia presentation and to find overlap is rare at best even though there are designers and companies trying to bridge that gap. To find undergarments as a trans* person can be a daunting and mentally exhausting task because there can be feelings that you don’t actually matter involved in the process because there are very few if any available to you, that cater to you and your needs. As someone who has chosen to and been able to go under the knife I don’t have to think about shopping for undergarments anymore and I will admit I do take it for granted sometimes and have to constantly remind myself where I came from in my journey and how thankful I need to constantly be because I used to have to be in pretty significant pain for long periods of time to feel beautiful in my undergarments.


How can undergarment professionals (sales people, bra fitter, shop owners) make it easier or better for you to shop for undergarments? 

I think that sensitivity training needs to be a necessary step to being on the sales floor.

What brands do you love and why? Are there any that you feel really serve the trans and non binary community?

Unfortunately I don’t know of any brands that accessibly service the trans* community when it comes to undergarments and I wish I didn’t have to say that. I definitely belong to, what I assume, is a large group of people who view Victoria’s Secret as the mothership of undergarments because that’s just what I know. I do enjoy how beautiful their undergarments make me feel and how empowered I am with a nice matching bra and panty number—matching underwear, who knew it was that simple, right? Thankfully though I know an undergarment expert who can help me branch out into the world of lingerie 😉

What specific products do you love and why?

My secret weapon, ride or die, couldn’t live without it product back in the day was waterproof KT sports tape. It made tucking exceedingly more comfortable and I would budget it in because it is a little more of an expensive item when bought consistently. Now, I feel like I can take on the world with some concealer, a nice false lash and bright matte lipstick…and highlight…LOTS of highlight.

What do you wish existed or there were more of when it comes to undergarments and lingerie for your community? 

 Accessibility, accessibility, accessibility. I can count on one hand, with fingers to spare mind you, the number of brands I’ve encountered through my transition that cater to trans women/trans feminine people specifically. With that said, they cater in the sense that they make a few products that are helpful to trans women/trans feminine individuals but they price themselves out of being a realistic option. Poverty and homelessness is essentially an epidemic in the transgender community as a whole, specifically trans* persons of color, and it’s not realistic to spend upwards of $200 on a bra and the full cup inserts to go into said bra, or $70-$100 on tucking undergarments. The effort is there by creating products for the trans* community however if those products aren’t realistically accessible I can’t justify it being an option.

What’s your advice to someone who feels marginalized, misunderstood, or confused about their underwear options as a trans and non-binary person? 

 I stand by putting your personal comfort first. There is a time and a place for taking certain, often painful measures when it comes to wearing undergarments and I truly see it wise to put your comfort before fashion as much as possible.


Pooya Mohseni is an actress, writer, and advocate who lives in NYC, originally from Iran, and a woman of trans* experience.

Read more about Pooya

How do you identify? Are you trans, non-binary, etc? Can you explain a little bit about what that means for someone who may not know? 

I’m a Trans woman. What that means in very plain terms, as I see it, I was born a girl in a boy’s body. Or I was given a male marker at birth and when I became of age, I medically and socially transitioned into my true gender: a woman, thus “trans” woman.

How do you think your (or in general) gender identity relates to your undergarments? 

Our modern clothing is very binary, and so are our undergarments. I was never a frilly kind of girl, pre or post transition, but I was very aware that I wanted to wear women’s clothes. In its simplest form, that just felt right to me. I was wearing my mom’s undergarments way before I started to transition and nobody knew because it would have caused a lot of problems. But in the safety of my own privacy, I wore her clothes, undergarments, and dresses. And when I transitioned, I feel that I went through an androgynous phase which also included very utility oriented panties and sports bra type of things until I made a full transition and moved into satin and bikini bottoms and strapless bras.

What’s it like shopping for undergarments? Do you feel like you have to choose a section based on gender online or at a shop?

To me, undergarments are very gender based, either online or at a shop. So since I wear female undergarments, even if they are not overtly frilly, I still have to go to the women’s section or a store that specializes in women’s undies.

Have you ever had a bra fitting? And what was that process like? Was it trans/non binary friendly?

I have never hard a bra fitting and probably part of that had to do with not knowing where to find a trans friendly bra fitter.

How can undergarment professionals (sales people, bra fitter, shop owners) make it easier or better for you to shop for undergarments? 

As other stores have done, it would be beneficial if the shops make it known that they are trans/non binary inclusive so my community would feel safe and welcome entering their establishments, and also educate themselves in how to address trans and non-binary needs for undergarments.

What brands do you love and why? Are there any that you feel really serve the trans and non binary community?

I’m a loyal calvin klein and Victoria secrets fan, because I have a slim build and their undergarments fit me well. I’m not aware if they try to serve my community. I wish they would embrace us as a customer base: we wear undergarments like anyone else!

What specific products do you love and why?

Pre GRS [Gender Reassignment Surgery or Gender-Affirming Surgery], I used to wear a girdle/Spanx type of underwear to tuck. I did that for years and it was painful at first but then I got used to it, even though it made it so much hotter in the summer. As for bras, because I had very small breasts at the time, I owned a pair of water bras which had water in them and even though they were heavy, they gave me a fabulous silhouette.

What do you wish existed or there were more of when it comes to undergarments and lingerie for your community? 

I wish there were more pieces that allowed pre-op women to tuck, while being comfortable and more user friendly undergarments for trans men who otherwise “bind” their chests. These pieces exist but none of them are comfortable, and comfort, on a daily basis, should be an issue to consider.

What’s your advice to someone who feels marginalized, misunderstood, or confused about their underwear options as a trans and non-binary person? 

My suggestion is: Keep looking, keep asking. If it’s not comfortable, if it doesn’t make you feel confident about your body, look for something else. Above all, ask your trans/non-binary friends if they have had better experiences and if they have something that can help you. After all, that’s what a community is for.



Devlin is a Navy veteran, the writer of Fiercely Trans, and a woman of trans* experience

Read more about Devlin

How do you identify? Are you trans, non-binary, etc? Can you explain a little bit about what that means for someone who may not know? 

I am a transgender woman. What this means is that, when I was born, a physician examined my genitals and decided that I should be gendered male. As we now know, he did not have the necessary data to make such a determination. I identify, and am a woman.
To go into a bit more detail on my story, I knew something wasn’t right when I was very young, around three or four. I actually remember exclaiming that I wanted “to be a girl.” I don’t remember the exact consequences, but I do recall that I learned to hide that part of myself. At the time, trans identities weren’t a part of the overall collective consciousness, so my needs weren’t addressed. It wasn’t until I was nineteen or twenty when I first learned of transgender identities, thanks to Jennifer Finney Boylan’s press tour for her memoir, She’s Not There. I strongly identified with her struggle and began to identify as transgender. Unfortunately, it was nearly a decade before I was emotionally strong enough to come out and begin my transition. But now, I’m here and after three years, I am an out and proud trans woman, enjoying my life far more that I ever did before.
How do you think your (or in general) gender identity relates to your undergarments? 
I did grow up with some curiosity about feminine undergarments, but I always kept things very separate. Before learning of and acknowledging my identity, I thought of dressing in women’s clothing as crossdressing and I felt shame around it. I only wore feminine undergarments when I was dressed in full women’s attire, and when I did so, it was usually privately and just to have that feeling of “rightness” I felt when I could express my feminine side.
I think from early on, and continuing to today, a bra feels very feminine to me, and while I’m as happy as most other women to take mine off when I am finished being out and about, the fact that I need one these days still makes me feel better about myself. I mostly wear functional underwear bottoms, but I have some pretty things for hot dates.
What’s it like shopping for undergarments? Do you feel like you have to choose a section based on gender online or at a shop? 
I shop in the women’s department, but I do find it can feel awkward, I just worry about people feeling odd about my presence, and making a deal of it, so once I’ve found what I like, I tend to order more online and avoid retail stores.  I believe I’m visibly trans, though friends tell me otherwise at times.
An issue for me is that in order to find cute underwear that performs according to my needs, I often have to go to websites catering to cross dressing. Cross dressing certainly isn’t a negative thing, but the sites usually feel a bit fetish-y and I just don’t feel particularly good about shopping at them.

Have you ever had a bra fitting? And what was that process like? Was it trans/non binary friendly?

I haven’t. I’m not particularly well endowed in the bust, and I do use padding, so as long as the band fits comfortably and the straps are adjustable, I’m typically fine.

How can undergarment professionals (sales people, bra fitter, shop owners) make it easier or better for you to shop for undergarments? 

That’s a great question I’m not sure I’m qualified to answer! If I went somewhere and they had some gender non-conforming staff, I’d feel much better about that place. Throw a subtle rainbow in your ads, maybe? I think undergarments are the only time I worry about shopping!
In the case of the online places which cater primarily to cross dressing folk, perhaps a separate online store front for trans clientele.

What brands do you love and why? Are there any that you feel really serve the trans and non binary community? 

I kind of like my Warner’s No Side Effects bras. They have wider panels for the under-arm side of the rib cage area. I have a long torso, and these are more comfortable and I think they look more cute on me. I have not had any breast augmentation.  I think that I want to, but it’s mainly a funding thing.  I had a very muscular chest prior to undergoing hormone therapy, and since then I have lost muscle and gained fatty tissue in the breast area.  It seems to be a bit more spread out on my body than that of cis women around my size.  My chest is a bit more broad in general.  To fill out a bra, I generally use the add-a-cup pads you can get in stores, the kind with some water in them so they have a bit of heft and weight and feel closer to real breasts.
Otherwise, for bottoms, my go-to functional daily wear are Vassarette’s Women’s Invisibly Smooth Brief Panties. I need undergarments that can keep me tucked, and these don’t leave any hint of V.P.L!  The only negatives are that they do not breathe well and aren’t exactly cute. I also have not had genital reconstructive surgeries.  Or, to be more direct, I still have a penis.  This is kind of along the lines of breast augmentation.  I would like to have the surgery, but I can’t afford it.  C’est la vie.  I’m very lucky in that having a penis doesn’t cause me significant dysphoria or distress, but I would rather not have it.

What do you wish existed or there were more of when it comes to undergarments and lingerie? 

I wish there were more cute (affordable) options for good panties that can hold a tuck. Since what I wear is shape wear, even though it’s pretty light, it still doesn’t breathe the best. So, perhaps some quality cotton panties with a bit of reinforcing in the crotch zone? I wear a lot of vintage style dresses, so if I’m wearing crinolines, can wear comfortable (and cute) undies, no problem.  Also, more cute lingerie choices for trans women who prefer to be tucked! I have a couple thong gaffs which are cute and lacey, but that’s about the limit of my lingerie bottoms.
I’d also like to try on a bra that fit my actual chest, anything with the correct cup circumference will typically be too deep to support my breasts. 

What’s your advice to someone who feels marginalized, misunderstood, or confused about their underwear options as a trans and non-binary person? 

Reach out to other trans folk. I’ve encountered many helpful people thanks to the internet. Get yourself a measuring tape and use size charts. Confidence is the key to shopping in person. Though I tend not to shop for undergarments in person, I have done so, and the important thing is to be sure (or act like you are) that you belong and deserve to shop for the items you need as much as anyone. And I think many of us whether cis or trans have had to fake it till we made it when it comes to confidence. You can do it!


Bex is the creator of the BexTalksSex blog and Podcast, and non-binary trans* masculine

Read more about Bex
How do you identify? Are you trans*, non-binary, etc? Can you explain a little bit about what that means for someone who may not know? 

I’m a non-binary transmasculine person. For me, being non-binary means I don’t feel like my gender fits neatly in the box of “man” or “woman”. I (like many other people) experience gender on a spectrum and feel like I fall somewhere in the middle, generally on the more masculine side of the spectrum (which is where “transmasc” comes in). I am AFAB (which means I was Assigned Female At Birth, I have a vulva and breasts) but I’m much more comfortable presenting as masculine and being perceived as a man. 
How do you think your (or in general) gender identity relates to your undergarments?

I feel like undergarments are almost inextricably linked to gender in our society and it’s really hard to try to unpack that, to the point where I think wearing undergarments that are traditionally coded as feminine (bras, lacey thongs, etc) would be extremely uncomfortable for me. Beyond that, most undergarments are designed to emphasize natural curves and bulges (whether that be the breasts, hips, penis, etc) so wearing the “wrong” undergarments for my gender would just emphasize exactly the parts I’m uncomfortable with. Alternatively, using the undergarments I’m comfortable with (boxers, binders, or sports bras) help to minimize the parts of my body I’m less comfortable with, while emphasizing others.

What’s it like shopping for undergarments? Do you feel like you have to choose a section based on gender online or at a shop? 
Luckily, it’s not awful. I’m often read as a woman [by others] and luckily it’s nowhere near as taboo for me to be seen in boxers as it is for someone who is seen as a man to be buying “women’s” underwear. It’s difficult to get my hands on good binders, especially because I have to go online so I can’t try them on. I did get a Victoria’s Secret gift card once and had to go in there to buy a sports bra. It was terrible.
Have you ever had a bra fitting? And what was that process like? Was it trans/non binary friendly?
The only time I’ve ever been for a fitting was at a Victoria’s Secret and it felt distinctly like an experience designed for very femme cis women, there was no space for masc women, let alone nb or trans folks.
How can undergarment professionals (sales people, bra fitter, shop owners) make it easier or better for you to shop for undergarments?

Stop making everything pink, for the love of god. Don’t sort underwear by gender; instead sort by style. Make more sizes (I am a very small boy, some Assigned Male at Birth folks will need larger sizes). Show people of all genders modeling your products in your ads. Don’t assume what I want out of my underwear, ask me. For example, the last thing I want to do is emphasize my chest, but that’s what many people would assume if I was shopping for a bra. Don’t assume who the underwear is for. For example, I’m not buying it as a gift. 

What brands do you love and why? Are there any that you feel really serve the trans and non binary community? 

I love GC2B. They make binders specifically for the trans* community and they’re some of the best ones I’ve used. As for boxers, I usually go to Uniqlo because they’re super soft and comfy, but they’re not especially trans friendly. 

What specific products do you love and why? 

GC2B half-binders, they compress my chest really well, are super comfortable, and aren’t long like other binders. They feel just like a sports bra, and they fit well under tank tops.
I also love Uniqlo Supima Cotton Boxer Briefs, they are the most comfortable things in the world and they’re tight enough to hold my packer in place while still being comfortable. A lot of things cut for “mens” bodies can’t accommodate my hips or is too tight around my thighs but this stretches comfortably around both and still looks good.

What do you wish existed or there were more of when it comes to undergarments and lingerie? 
More binder options! Ones that cover less skin (I like to wear crop tops or thin tank tops and most binders insist on covering my whole torso). Something that feels sexy and not just plain and restricting. I also wish it were easier to get simple, affordable, cotton boxers with pockets for a packer.
What’s your advice to someone who feels marginalized, misunderstood, or confused about their underwear options as a trans* and non-binary person?  
Focus on what’s comfortable, physically and emotionally, and try not to focus on what “should” be. Shop online or send a friend to pick stuff up for you if going into specific stores are uncomfortable.
Connect with Bex:
Blog BexTalksSex or Podcast


Cassie Brighter is the webmistress of and creator of the upcoming online summit at and a woman of trans* experience

Read more about Cassie
How do you identify? Are you trans, non-binary, etc? Can you explain a little bit about what that means for someone who may not know? 
I identify as a woman. I am trans*, binary.
My mind and heart follow the conventional traits related to women. My body presents traits conventionally related to men. I’m transitioning – adapting my body so that it better conforms with my identity, my thoughts and my feelings.
How do you think your (or in general) gender identity relates to your undergarments?
This is a wonderful question. Gender identity is validated or squashed by undergarments.
I have memories of trying on my mother’s bras as a teen, and eventually owning a few bras and panties as a young adult. I remember a feeling of empowerment, as well as a wistfulness, a wild longing full of “if only” and “I wish.”
Fast-forward two decades later, as I started to transition – shopping for clothes was filled with dread, embarrassment and uncertainty. In 2011, I wore bras only in private. In 2014 I began to present female in public, and wearing the right undergarments always represented a strong reassurance.
Currently I still have to present male at work. Wearing my preferred undergarments keeps me grounded and helps me retain my sense of self.
What’s it like shopping for undergarments? Do you feel like you have to choose a section based on gender online or at a shop? 
Shopping for undergarments has always been a challenge. I feel awkward shopping at stores. Shopping online is always hit-and-miss. Additionally, I am missing a lot of the learning that most girls get simply by going through puberty, sharing with their moms and their friends.
Have you ever had a bra fitting? And what was that process like? Was it trans*/non binary friendly?
I’ve never had a bra-fitting. I would welcome a trans-friendly bra-fitting, but I’m unaware of any such opportunity in my area.
How can undergarment professionals (sales people, bra fitter, shop owners) make it easier or better for you to shop for undergarments?
It would really help if the customer-facing employees had some basic indoctrination on how to comport themselves around trans* or non-binary people. A symbol or marker announcing that the store is trans*-friendly would be really useful. I’d love to see a trans*-flag sticker on a shop’s window. I’ve never seen that done.
Proper use of pronouns sets the tone for any further conversation. And demeanor matters. A smile, and offers to help in any way needed, would be appreciated it. I think it’s hard to understand for many cisgendered people how uncomfortable and/or intimidating a cis/binary world can be to non-conforming folks.
What brands do you love and why? Are there any that you feel really serve the trans and non binary community?
The big challenge with panties is that they don’t accommodate for my [male] anatomy. It’s very frustrating to see a cute pair of panties and immediately realize there’s no way I could make them work. I found a website called – it mostly has male underwear, but it includes frilly and lacy underwear. This is where I buy some of my undies.
I found two online stores for purchasing swimwear: and Both have some one-piece swimsuits that include a small skirt, which makes it possible for me as a transwoman to wear these. (Most swimsuits are unwearable because of the exposed crotch area).
What specific products do you love and why? 
I love gaffs [underwear used to aid in “tucking” male anatomy], although I still haven’t found one that would do the job perfectly. I like post-mastectomy bras which include a prosthetic form inside (I wear a prosthetic now while my breasts develop, and I really don’t like to have the prosthetic fall out as I remove my bra).
I love frilly and lacy panties. I’d love to find matching pantries/bra sets thats I could wear comfortably.
What do you wish existed or there were more of when it comes to undergarments and lingerie? 
I’d like to see gaffs that are pretty. Currently I wear a gaff and then panties on top. I’d like to see more options for swimsuits. I’d like to find a way to wear shorts.
What’s your advice to someone who feels marginalized, misunderstood, or confused about their underwear options as a trans* and non-binary person?  
My advice is to find community. Community empowers, and help heal wounds from the constant micro-agressions. Good places to find community are the local LGBT Center, or groups on I am in the process of building a community site for transwomen called


Your Turn: Are you a person of trans* experience? If so, what has your experience been like shopping for undergarments? What brands and styles do you like, and why? What do you feel is missing? What do you want people to know about your needs and desires as a trans* person? What loving steps can you take to say hurray for lingerie?

Do you work in the lingerie industry? How can you support and include this community? In what ways are you already doing so? And what steps can you take to make sure you are supporting their actual needs, and not just surface level needs?

Are you not a person of trans* experience? What came up for you while reading this article? What doors opened for you in your heart? What surprised you? How can you support this community? What can you personally do to create a more loving and inclusive world, for people of trans* experience and beyond?

Leave your comments here (please be respectful and caring. The people interviewed here are brave and loving to open up their inner thoughts and needs with you. Rude or lewd remarks will be deleted.) or write them in a journal, or share them with a friend. Whatever you do, I hope are taking a loving step to say hurray on the inside, outside, and underneath!

xoxo kimmay

A personal note: I feel really happy to have the blessing on this topic by the people of the trans* community that I interviewed. Several times, they’ve told me that I am their ally and advocate, and welcomed me with love and support. I am so thankful for this, because I am trying my very best to show up with sensitivity to a topic where I have no personal experience. I’m so happy to have the support to overcome my own doubts, so that I can help YOU overcome yours. If this article has inspired you to open your heart a little bit more, your mind a little bit more, and your self a little bit more to new pathways of love – then hurray. It was all worth it.

A special thank you to Maison Close and Playout for providing samples or donating styles to be worn for this shoot. A massive thank you to Laura Boyd of Own Your Sexy and Own Your Brand for the amazing photographs. And a formal thank you to the interviewees for their time and effort – especially to Nicki and her mom, Nancy, for making the trip to New York City.

Other resources:

Special thank you to Kathy Mills of Outright for providing several of these resources.