As an Undergarment Educator and Coach, Kimmay Caldwell uses undergarments as a tool to support people. She has fit thousands of people for cup sizes AA to N since she started in the Intimates Industry. Whether people spend $150 or $15 on a bra, everyone faces challenges when it comes to the mirror in the bra fitting room. It’s an intimate opportunity to help people let go of old stories and embrace the fullness of who they are. Every person deserves comfort and confidence – in their bra and beyond. Kimmay truly believes that a well fitting bra can help a person stand tall, lead with their heart, and say hurray!
We were curious as to how Kimmay found herself in the industry and asked her to answer a series of questions that provide insight for any of those looking to take a similar path.
Lingerie is such a unique industry to get into. What drew you towards building a career in it?
The money! Ha! I was really broke when I started in lingerie. I was making $7/hour and living completely independent in NYC while putting myself through college. I was desperate for more money. My friend said a bra shop was opening up and wondered if I had any interest. I didn't care about bras at all, but when I found out they were paying $10/hour, I jumped at the chance. I was hired on the spot and the rest is history.
What really kept me in the industry though was the experience in the bra fitting rooms. I had just turned 20 when I started and had no idea what I was in for. At the time I had a very negative body image, even with all of the privileges of being thin, young, healthy, able, and white presenting. My body, like all bodies, wasn't perfect and didn't match up to the airbrushed images I saw in magazines. This was 2005, before body positive or anti airbrushing movements. So when I saw real human bodies, my eyes were opened. I witnessed every kind of body you can imagine. This was SoHo, so every walk of life came in to get a fitting!
Not only that, but I also witnessed every person say something negative in the mirror. I was so surprised that they all thought the same negative things about their wonderful bodies. It was then I realized talking to myself that way was a waste of time. So I started talking kinder to myself, and started helping other people do the same. I always say that bras are worn right over the heart, so they have a special opportunity! If there is any shame, confusion, or discomfort in that area it can totally block off the heart. Wearing a well-fitting bra brings comfort so you can stand tall with your shoulders back and heart out; and make heart led decisions. I love helping people take steps to make the routine of putting on a bra into a ritual. If you can start each day with a hurray, feeling empowered about what you put on over your heart, imagine the long term effects that has on a person. It will change their life, and then they can go out and change the world.
From that small shop I went to Saks Fifth Ave, then La Perla, and finally after working as a marketing director for that same small shop for years, I started Hurray Media LLC. Flash forward and I have now supported thousands of folks in person and millions around the globe through things like my blog, TV, or TikTok. Though I don't fit in a shop any longer, I do train other bra fitters and I love to serve and support bra wearers with education!
What are some things people may be surprised to learn about the bra/lingerie industry?
Many people think that working in lingerie is really glamorous. And some parts are! I love going to Paris, buying pretty things, and helping people feel fabulous. And. There is a lot of work that goes into this business and it's not all glitzy.
As a bra fitter, people thought maybe I was just trying on fancy bras all day and fitting other women in some kind of sexy film. But the truth was I was helping people's grandmas, and moms, and sisters. They have regular bodies, come in sweaty, are nervous and have insecurities, are on a budget, didn't groom that day, etc. It takes a lot of work to navigate people's self-esteem issues and also find a garment that fits well on their unique body, and fits their requests. I would be so busy some days that I would forget to eat or not have time to pee. It was wild! And like any job that serves people, I have loads of wild stories about customers.
As an Undergarment Educator and owner of my marketing company, people are so confused about what I do. They think I make lingerie, fit people for bras, sell underwear, or just model it. I have never designed lingerie and don't own my own shop. I partner with brands to wear and share their products, while educating consumers and bra wearers everywhere. I also train fellow fitters, consult with brands on marketing and industry strategies, product shoots and create content, host TV segments, and organize special events and workshops. It's a LOT of work and not a single part of it includes me designing undies.
What do you look for when purchasing a bra?
Personally I subscribe to The Comfort Fit System™ which means comfort equals fit, and fit equals comfort. I don't wear bras that don't fit well. I can't do it. Not only because I'm a fitter, but because I'm very sensitive to materials and sensations, so it has to fit well or I will rip it off. That said, I have plenty of gorgeous lace items, smooth t-shirt bras, stretchy lounge bras, and even bra-free compression tanks. I wear it all!
When I'm in Paris, I often look for special pieces that make me say hurray! I am gifted many products, or sent items for my client work, so truthfully I don't need another bra. I have over 200 or more by now! So, if I DO buy something, it needs to be special. Usually that means gorgeous lace, a fantastic color to show off with a specific outfit, or something really sassy.
What is something you wish you had known before you started in the industry?
Oh gosh, loads! First of all, working in this industry has taught me so much. I truly think everyone should be a bra fitter for a week. Not only to learn the basics of bra sizing, but also to see real human bodies and support people with something truly sacred. I am so thankful that I started as a bra fitter at 20 and was exposed to the secrets of the fitting room. It opened my mind and my heart in massive ways.
That said, I wish I'd known how people rarely leave this industry. For real! People stay in lingerie and never leave. Or, they go for a time and come back. For me it's been 18 years so far. Anytime I meet someone new to the industry I often say, "Welcome! You're never going to leave." We all stay, though, because to us this industry is so much more rewarding and needed than clothing, shoes, or purses. We all know that what we do really uplifts and supports people in more ways than one. And that feels good!
Where do you think the intimates industry is headed next?
I have about a zillion ideas here. Ha! But the biggest thing is accessibility. As someone who lived in NYC where there were plenty of bra shops, I never really thought about this. But I moved to rural Oklahoma for three years recently, and the only bra shop in town was Wal-Mart. People would drive 2.5 hours just to go to Victoria's Secret. With more education from folks like me on TikTok and my course, Bra Confidence & Comfort, more and more people are finally understaning fit and how important it is. They don't want to to settle. So I see bra fitters become a respected, highly skilled trade and more shops popping up.
That said, there will always be people who want simple, smooth comfort and convenience. So wire-free, smooth bras that are easy to order online will still rise in sales.
I do see more AI and scanners and fit quizzes coming into play. To be honest, I think fitters and technology will need to work together in order to truly serve clients. I don't think we can EVER replace bra fitters. But I do feel AI could be helpful in making bra fit more accessible to those who don't have a local shop or expert in the area.
And I also see more gender fluid options in lingerie emerging. It's such a binary industry because it covers genitals, which reflect sex, and which have been confused with gender. In some ways, that's actually really affirming for folks who want to reinforce their gender identity as female or male. But it's also lacking in nuance. Men's lingerie is growing. Non-binary options exist. Undergarments to support trans bodies are more prevalent. More and more items will be designed with more genders in mind, both by their materials and fit, and their marketing. Personally, this gets a hurray from me.
Check out Kimmay's website here.
Follow Kimmay on Instagram here.
