I can see it now. It’s happened several times. A woman I’m meeting, who knows that I’m a long time bra fitter and lingerie enthusiast, introduces herself and with great embarrassment and implied apologies, says something like “I know you love bras, but I actually loathe them and never wear them. Don’t hate me!” or asks me “I actually don’t like wearing bras…but you obviously think everyone should, right?” It’s a pretty big question. I mean, do you HAVE to wear a bra? It’s time to set the record straight. Here’s what I think about this complicated and important topic!

First thing’s first: You don’t HAVE to do anything. Seriously. No one, including me, can tell you what to do with your life, or your breasts. I often tell people that I am not a “bra Nazi”. It’s a terrible term, I realize, and I mean no offense to Holocaust survivors. I use it because I want people to know I’m not going to come to their home, terrorize them in the middle of the night, and scream “Why don’t you wear bras?!” It’s not that serious. I love bras, and I absolutely think that a well fitting bra can help a woman stand tall, lead with her heart, and say hurray. But it’s also just one tool I use to do that, and I realize that they’re not for everyone.

Shocking, right? You’d think that a woman who has been devoted to bra fitting, braducation, and undergarment awareness since 2005 would be “pro bra” all the time. So here’s the deal.

Anything done in love is worth doing. Anything done because of hate is a waste of time. 

It’s that simple, but let me explain.

If you are not wearing a bra because you “hate bras”, this is not a very hurray thing to do. In fact, if you “hate bras” because they are uncomfortable, I actually suggest that we discuss fit, size, and style to find something that feels great for you. I’ve helped many bra haters learn to love bras, and more importantly, this important part of their bodies.

I think refusing to wear a bra because you “hate bras” is a waste of time. I think choosing to love, honor, and embrace your breasts by not wearing a bra because you love the way your breasts sway when you walk without a bra on, or you enjoy the ease you feel without a bra on, is worth your time. And vice versa. I think choosing to wear a bra because you hate how people react to you if you’re not wearing one is not super helpful. And choosing to wear one because you love the security or confidence you feel in one is a great choice. Just make sure the action you’re taking is done in love. Always.

Do you HAVE to wear a bra? Find out on Hurray KimmayStyle notes: Above, I’m wearing a pair of Falke thigh high stockings, and a Gossard bikini and garter belt. The tux jacket and photo was provided by photographer Laura Boyd of Own Your Sexy. Makeup and Hair by Zuleika Acosta.

A few reasons when or why to wear a bra: 

  • To support your breasts and keep them up off of your torso
  • To shape your bust into a desired shape
  • To create a desired silhouette underneath your clothing
  • To feel supported and embraced, like wearing a hug
  • To conceal nipples
  • To adorn and decorate your body
  • To express your personal style and true colors {more below}
  • For comfort {more below}
  • For confidence
  • To avoid staring and judgement in public {more below}
  • To work or in public
  • To sleep (non underwire only, please)
  • Health concerns or physical issues – post surgical bras, for example
  • To say hurray

A few reasons when or why not to wear a bra: 

  • To explore your body in its natural form
  • Style or built in support {more below}
  • To sleep
  • Around the house
  • Running errands
  • Comfort {more below}
  • For women’s rights {more below} 
  • Health concerns or physical issues – after a serious burn injury or accident, for example
  • Post surgery – after a mastectomy or augmentation you may not need or want to wear one
  • To say hurray

Let’s dive deeper on a few of these…


Let’s start with the #1 one reason a lot of women I know wish to go without a bra: comfort. Think of bras like shoes. If you are wearing the wrong size (too small or too big), or a style that isn’t a good fit for your feet or level of physical movement, walking around all day will feel pretty painful, right? But if you’re wearing a pair of shoes that fits well and feels great, wearing shoes can actually be pretty comfortable. In addition, they can protect your feet from the ground and wear and tear of walking around all day. That’s how I feel about bras. Believe it or not, many women who “hate” underwire bras, or “hate” bras in general, citing that they feel constricting or like torture, just need a size or fit adjustment to reap the benefits of a well fitting bra. I’ve fit thousands of women who were ready to give up on bras, and this is almost always true! Want to explore this? Check out my top tips for checking fit, and get your bra size starting point. Plus browse my resources page for loads of other help.

Do you Have to Wear a Bra? Kimmay in peach on Hurray Kimmay
My friend, Liz C., who wears a 34H relayed that comfort is her #1 reason for wearing a bra. I know that many people skip the bra to feel comfortable, but Liz actually feels more comfortable when wearing her bra. She told me that once she ventured down the staircase in her apartment building to answer the door wearing pajamas, sans bra. While descending the staircase, she felt the need to physically hold her breasts with her hands to stop the bouncing. You see, Liz felt comfortable and confident enough to answer the door without a bra, but the physical pain she felt from walking about without support was too much to bare. Liz adds: “The act of being seen without wearing a bra is not a thing for me. But the physical discomfort of going without a bra is not enjoyable”.

Style notes: Above, I’m in Puerto Rico on the #HurrayVacay and wearing the peach captivating demi bra, with a matching thong (coming soon!) and the coziest flyaway cardigan in Navy. Photo by Becky Yee.

Personally, I love the support and security I feel when wearing a bra. It feels good to feel tucked in, held, and supported. I feel like I’m wearing a layer of love. If that’s not how wearing a bra feels for you, I encourage you to explore the fit, size, and style of bra for you. Just like shoes, there are many options and things to learn about the shape of your breasts, the multitude of bra styles, and the needs that you and your body have.Kimmay wearing peach bralette cardigan and panty in Puerto RicoI also love to wear a bra to sleep a few days before and into my menstrual cycle. During this time my breasts are more heavy, full, and tender. Having a soft, stretchy bra on feels so good. Many women practice this same thing, and the number of women doing this gets even higher when it comes to pregnancy. Try a sleep or travel bra, or any wire free bra style and see how comfortable it feels at night or in a long car ride!

Style notes: Above, I’m in Puerto Rico on a #HurrayVacay and feeling so cozy in a peach simply soft bralette, super soft flyaway cardigan, and a new hipster (coming soon!)  Photo by Becky Yee.

Beyond physical comfort, going with or without a bra can help you be comfortable with yourself and who you are. When I was at the third annual Wild Woman Fest recently, facilitating a workshop on loving your bust, I noticed that many women went without a bra. (Well, many women went without clothes in general – things get wild up on the mountain). So I asked for some insight into why. One woman shared that she felt like she could be 100% herself and love her body fully while in such a supportive environment, so she went without a bra at the Fest, but planned to wear one when she went back home. Of course, if you’ve taken loving steps and actions and going sans bra feels the best – go for it! Whether it’s just around the house or all the time, you get to decide what to do with your bust.


One of the biggest reasons to wear a bra in the first place is to wear it as an undergarment. In other words, bras can help the clothes you wear look great and your personal style shine! Breasts are accessories (I mean this in the kindest way possible). You can push them up, press them down, decorate them… it’s really up to you! You get to decide (within reason) the shape they can take. Go pointy, round, smooth, sassy, pushed up, pressed in – it’s up to you and how you want to look that day.Kimmay wearing different outfits and bras in new blog post on Hurray Kimmay
In addition, you can also play with making a bra a part of your outfit. Show off a beautiful color, let a little lace peek out, or jazz up a basic outfit with a pretty bra underneath. A few resources to explore this:

Style notes: Above (from left to right) I’m in Puerto Rico on the Hurray Vacay! 1. Bralette and Dress, Express. Hat, Gap. 2. White top, Marshall’s. Strapless bra, LeMystere. Cotton shorts, Old Navy. Sunglasses, Under Armor sunglasses. 3. Red bra, OnGossamer. Queens shirt, Lockwood Style in Astoria, NY. Sunglasses, Marshall’s. Shorts, H&M. 4. Romper, Marshall’s. Vintage belt, my Grandma. Push up bra, Adore Me. Sunglasses, Marshall’s.Kimmay in PR jumpsuit and no bra on blog post on Hurray KimmayOn the contrary, your personal style may call for you to go without a bra. I do this sometimes when my outfit has some kind of built in support, like the halter jumpsuit I’m wearing here in Puerto Rico. The way that this garment is structured around the bust, and with the deep V cut front, it makes sense for me personally to go without a bra. Instead, I’m wearing some nipple covers to keep them from showing through. (Of course, it’s up to you if you want your nipples to show or not.)

Style notes: Above, I’m wearing a jumpsuit from Forever 21, necklace from LOFT, heart sunglasses from a street vendor in NYC, and nipple covers from DIMRS.

And remember, just because it doesn’t show, doesn’t mean it’s not part of your style. While many women went without a bra at the Wild Woman Fest, a few had a different view. Amy G. is 40 and has a “love hate relationship” with bras. She used to only wear them in public, because she had to. But as she has aged, she has changed her story. She shares my belief that wearing a bra that suits her personal style is a great way to say hurray throughout the day. Adorning her body and bosom with pretty lace, sassy colors, and delicate designs puts a smile on her face. And most importantly, it can be her sexy secret. Even if no one else sees it, she knows she’s wearing it. I mean, I felt like she was preaching the Hurray for Lingerie mission! Wear it for you and to say hurray inside, outside, and underneath. Hurray!


OK – tricky topic warning. Ready?

For years I felt like maybe I wasn’t a good feminist or was not standing up for women, because I was giving in to the patriarchy if I wore a bra, cared about makeup or my hair, or liked to wear dresses. It was a struggle for me to own my version of femininity without feeling like I was giving in to an outdated societal idea. This is something I’m still working on – but am moving past. After the years of pretending not to care about things like makeup, bras, and dresses in order to fit in with the cool feminist kids, I realized that I was lying to myself. Quite frankly, I was dimming my version of feminine energy and what was true for me. I was doing the opposite of embracing my personal version of womanhood. Wearing bras feels good to me. It feels fun, supportive, loving, and light. They make me say hurray.Kimmay wearing Anita Fleur

Style notes: Above I’m wearing an Anita Fleur Underwire Mastectomy bra and matching panty with a peach simply soft robe in Puerto Rico.

But what if bras don’t make you say hurray, or you feel like you “have to” wear them in public in order to be presentable in society? That was the struggle that one full busted woman felt when she came into the bra shop where I was working years ago. She was filled with fire and hatred, as soon as she walked in. My colleagues and I asked how we could help, and she said: “I need a bra. I do not want to wear one. I think it’s stupid that I have to, quite frankly. But the society that we live in makes me have to wear one in order to be taken seriously, and not get stared at. I can’t walk down the f***ing street without being stared at unless I tame these breasts down and strap them in.” Wow. I mean, I can still feel her anger and resentment for feeling like she had to be something or someone she is not. It was a heavy load she was carrying around with her. And her action for wearing a bra was coming from a place of hate. We assured her that we didn’t think she “had to wear a bra”, but if she wanted one, we could help her find something comfortable, smooth, and supportive. I’d like to say that we did our job. In fact, we found her a great fit in a cup sized, wire free, smooth, sports bra. But she was still not satisfied. She bought it with quite a bit of indignation… and returned it a few days later. I saw that coming a mile away.

I wonder what would happen if I ran into that woman now. I wonder if I could help her come from a place of love. She may not feel like she fits into the society that she is in right now, and in order to fit in she has to do something she doesn’t want to with a sacred part of her body. That’s a bummer. I get it. But what if the place was “I lovingly choose to find a bra that fits well and feels great so that I can go to these meetings and interviews and show them the work that I do and the love I pour into my job. I choose to put the focus on that instead of my bust. I acknowledge that I love my body and breasts as they are, and understand that not everyone is there yet.” This is a toughie. What are your thoughts on this?

My friend Kat had an interesting perspective. She shared a memory of being in line in college with two other girls, when they noticed a classmate who very often went without a bra. The other two women, with disdain and disgust, described their classmate as someone who was showing off, asking for attention, and probably “a slut”. In fact, they whispered “you can even see her brown nipples through the shirt!” Kat couldn’t help but think of her own dark, brown nipples. And it made her think that going without a bra was distasteful and that nipples should be hidden. Especially if they’re dark. This experience is what makes her double and triple check if her shirt is too sheer when she runs to grab her laundry without a bra, and usually prompts her to put one on. It’s a big reason she won’t go without a bra now. It was a lesson in shame. Sigh.Kimmay wearing tux jacketWe have the opportunity and responsibility to navigate how the world views us and how we want to show up in it. It’s a constant state of learning, I find. While I’m tempted to say “screw society and wear whatever you want!” I understand that is not always possible. Sometimes, choosing to show up fully is a way to say I love myself and my breasts. And sometimes, the most loving act you can take for your breasts is to guard them against the world: lurkers, mean girls, employers, etc. Find your own way and say hurray.

Be gentle with yourself, and don’t judge yourself or others too harshly. We are all doing the best (or breast!) we can. Take it one step at a time to love your body, own your sexy, honor your bust, and figure out the balance for yourself.

Your turn: what do you think about wearing a bra? Are there certain times when you do, and some when you don’t? Do you hate to wear a bra? Do you love wearing a bra? Did anything you read here give you a new perspective?

Leave me a comment here, or send me a tweet!

xoxo kimmay

PS: as always, zero photo shopping to my body here. I am wearing makeup (sometimes more than others) posing to look and feel my best, but my commitment to you is to never airbrush away “imperfections” so that you can see what a real body looks like. Join me on the journey to love your body!