Kimmay in front of cube-painted brick wall

Meet Kimmay

Undergarment Educator & Coach

When you look in the mirror, what do you see? When I was 19, I didn’t like what I saw. My inner dialogue was worse than a gaggle of mean girls. I was putting unfair expectations on myself and my body. It was stopping me from loving myself, allowing others to love me, and showing up confidently as the real me. Among other things.

It wasn’t until I started as a bra fitter in a small shop in NYC and saw real people’s bodies – not the false perfection shown in magazines – that I started to appreciate the gift that I had been given. I also started to see the beauty in others. But what surprised me, was that almost every person who walked into the bra fitting room – mother of three, young, old, supermodel, breast cancer patient, trans individual – had something negative to say to themselves in the mirror. I was shocked! Something had to change. I knew I wanted to say hurray. It was then, in 2005, that

I decided to change the conversation I was having with my body, and eventually my whole self, and to help other people do the same.
Like you.

I had such a positive experience, that I have already shared stories about it with multiple friends and will continue to do so. I certainly feel more knowledgeable and braducated. Thanks, Kimmay!

Ferna Hall
Bra Drawer Audit and Shopping Client

Kimmay in mirror

As an Undergarment Educator I use undergarments as my favorite tool to support people, and even as a coaching tool. I have literally fit thousands of people for cup sizes AA to N since my start. I’ve helped people in that family owned shop, and at fancy stores like Saks Fifth Avenue and Bergdorf Goodman when I worked for luxury lingerie brand, La Perla. Whether they spend $150 or $15 on a bra, all people face challenges when it comes to the mirror in the bra fitting room. And it’s an intimate opportunity to help them let go of old stories and embrace the fullness of who they are. Every person deserves comfort and confidence – in their bra and beyond.

I truly believe that a well fitting bra can help a person stand tall, lead with their heart, and say hurray. And it’s not just about bra fitting. With coaching, articles, videos, events, and more, Hurray Kimmay is a go-to resource for you. Not just for expert bra fit tips, but for ways to support you holistically. I’m here to help you uncover your confidence, stand in your power, and to learn to love yourself inside, outside, and underneath™. Hurray!

Kimmay in mirror
Kimmay measuring

In addition to Hurray Kimmay, I was a fashion, beauty, and relationships writer at, and a regular contributor to The Lingerie Journal.

I also work at big lingerie expos, teaching bra fitting basics (and how to use compassion in the fitting room), as well as hosting panels and workshops. And I am often on TV and in the media. You may have seen me on The Today Show, The Rachael Ray Show, Tim Gunn’s Guide to Style, or The Martha Stewart Show where I share my expertise and my heart with millions of viewers.

Plus, I am the owner of my own lingerie content marketing company, Hurray Media. I partner with brands to empower and encourage people while sharing their products. I’m not just a bra fitter, writer, or marketer. I am your soulful sister on the same journey to saying hurray. Whether it’s one on one, in a small group, or with millions – I’m proud to share my journey with you, and I’m so excited that you’re here!

When it comes to bras, Kimmay Caldwell knows her shit.

Amanda Richards
Writer, Bustle

On Hurray Kimmay, you’ll find things about:

Inside: Your relationship with your inner self. Yoga, meditation, your soul, confidence, inner voice, inner beauty, healthy foods, women’s circles

Outside: Your relationship with the world outside of you. Your job, environment, home, style, fashion, personal branding, shining from the inside out

Underneath: Your relationship with your body and what’s underneath your clothes. Bra fitting, undergarment solutions, lingerie style, and your beautiful body

You’ll also find photos with no airbrushing or photoshopping on my body on this site. I realized it was one thing to talk the talk, and another to walk the walk. I started by posing in my bikini in O Magazine, then started taking images in my swimsuit and lingerie all around the world in places like Paris, Guatemala, Puerto Rico, and Mexico on the #HurrayVacay campaign with that same commitment lovingly sharing my true self with you. And guiding you to show up fully in your own way, too.

3 Ways to Learn on Hurray Kimmay

The Class

Start here! Watch Kimmay's class, How to Find a Comfortable Bra Fit For Your Body Without Wasting Money on Bras You Drea Wearing + her go-to Bra Fit Guide are your free! Take 60 minutes of me-time (plus get a peek at The Bra Confidence & Comfort Course + a special surprise)!

The Course

Kimmay's signature course, Bra Confidence & Comfort™ demystifies bra shopping and turns wearing a bra from routine into ritual using The Comfort Fit System™ and 18+ years of bra fitting experience. Includes 4 modules, bonuses, shopping guides, and more!

The Blog

Not only has Kimmay been fitting folks into bras since 2005, she's also been writing about them (and so much more!) Search the blog shopping guides, how-to's, Q&A, and more. Along with bra support you'll find inspirational posts and motivation, too. Hurray!

I have been handling the public relations for intimate apparel brands for over 15 years. I can say with ease, that Kim is one of the most knowledgeable bra fitters I have had the pleasure of working with. Plus, she has a great sense of humor!

Heather Patt
Owner and Director, Heather Patt Public Relations

Kimmay on Rachel Ray Show

Hurray Kimmay

As Seen On

Since starting in the lingerie industry as a bra fitter in 2005, Kimmay Caldwell has appeared in over 100 press outlets, including numerous TV shows, many magazines, and lots of websites. Her very first TV appearance was LIVE on the Martha Stewart Show on NBC as a representative for La Perla, back in 2007. Since then, she’s also appeared in or on:

TV: The Today Show, The Rachael Ray Show (9 times!), Tim Gunn’s Guide to Style, The Martha Stewart Show, The Better Show, The Marilyn Denis Show (12 times!) and more

Magazines: Brides, Women’s Health, Real Simple, O Magazine, OK Magazine, and more

Online: Bustle,,, The Huffington Post, and more

Online video and Facebook LIVE: HuffPostLIVE, Bustle Live, SheKnows Live, Look TV, and more

Commercials: Warners

Kimmay on Rachel Ray Show

Click to Watch Kimmay on TV!

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The Rachael Ray Show

Kimmay has appeared on The Rachael Ray Show 5 times (so far)! Explore some behind the scenes info and shopping suggestions, along with recaps of Kimmay’s trips to talk with Rachael about bras!

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The Marilyn Denis Show

Kimmay ventured up north for 5 different episodes to teach Marilyn Denis, host of the most popular lifestyle show in Canada, how to find two bra size starting points, when to buy maternity bras, and so much more!

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The Today Show

Kimmay joined Megyn Kelly Today LIVE in the NBC studios at 30 Rock to discuss some of her favorite bra fit tips, how to hide nipples, and fun ways to show off your bra!

Let's Connect

Want to book or interview Kimmay?
Kimmay Caldwell is the leading on-camera bra fit and undergarment education expert in the USA and Canada. In addition, she is a well-known leader in the self-love and confidence movements, and uses her bra fitting knowledge to support her work in helping people say hurray!

Beyond press mentions and features like these, Kimmay is also a popular panel host, workshop teacher, and women’s circle leader on various topics from bra fitting with compassion, sustainability and inclusivity in intimates, confidence and self-worth, moon circles, and more.

Get in touch to book her today!

PS: Are you a brand that wants to partner with Kimmay? From sponsored content to special events, Kimmay and her creative team are ready to authentically share products that are a good match and help folks say hurray! Use the contact link above to get started.