A Conversation with Kimmay Caldwell of Hurray Kimmay: Building Confidence Through Lingerie
TL;DR — The Heart of the Conversation
I chat with Kimmay Caldwell, founder of Hurray Kimmay Media, LLC to explore the transformational power of lingerie—from the fitting room to entrepreneurship.
We cover body image, sizing shame, the sacredness of undergarments, and how honoring yourself inside, outside, and underneath can ripple into how you show up in the world.
This is a deeply personal, beautifully honest conversation between two women building companies with purpose.
The conversation below has been edited and condensed. To listen to the full conversation, head to The Sustainable Undress on Substack!
Introduction
Micki:
Kimmay, I’m so excited to chat with you today! For those who don’t know, you’re an undergarment educator, self-love coach, and founder of Hurray Kimmay Media LLC. You’ve helped thousands of people find the right fit, from cup sizes A to N, and your expertise has been featured everywhere from The Today Show to The Drew Barrymore Show and in major publications worldwide.
You were a huge part of my early days of figuring out what Petal +Ash could be, how to approach things from a customer fit first perspective. This is really important because I came to this journey as a customer first. Beyond that, you've become a friend and someone I deeply admire. The heart led work you're doing is really inspiring and exciting. For people who don't know you, can you share a little bit about your journey and what led you to become an undergarment educator and found Hurray Kimmay?
Kimmay Cauldwell in Paris. Photo by Paige Gribb.
A Life-Changing Job
Kimmay:
Thank you! First of all, a quick note about us working together—I was sort of nervous, because I'm not a designer, but I loved our conversation so much, and really felt like I just wanted to support this woman. I loved working with you.
I always joke around and tell people that I got into undergarments for the money, because I was selling shoes for $7 an hour in New York City, putting myself through college. I was completely financially independent at 18 years old, and I was really, really broke. A friend of mine knew this, and asked me if I was interested at all in bras; she knew somebody who was opening up a store in SoHo. And I said,” I don't care about bras, but how much do they pay?” She said ten dollars, and I thought, “Oh my gosh, I’m going to be rich!”
But what was supposed to be a college job to get me through school, so that I could eventually be on Broadway—as we share this love for theater—was totally life altering. At 20 years old, which is when I started in 2005, I was so obsessed with needing to look a certain way in order to be considered successful. Especially going to school for musical theater, it was all about how I looked, and I did not measure up to the perfectly airbrush images I was seeing in magazines at the time. This is before Instagram and the body positive movement. At the time, I didn't have any examples of what real bodies look like.
I encourage everybody to work as a bra fitter for one week in New York City, because I was witness to what real human bodies look like, and the very real insecurities that everybody has. The fitting room is such a vulnerable and revealing place. People would come in and take off their clothes and tell you everything. They would say things out loud about their bodies and make apologies for them, and excuse away very natural, beautiful things about themselves. I realized I had been doing the same thing. I thought, “This is such a waste of time. I'm going to start talking kinder to myself and my body and help other people do the same.” Very quickly I was able to help people find bras that fit, which is already life altering for people. But I was like, while we're here, why don't we look at who you're talking to in the mirror and how you talk to them. So kind of accidentally, at the ripe age of 20, I started coaching people in the bra fitting room.
Returning to What Matters
Eight months in, I was recruited by Saks Fifth Avenue, and soon after, by La Perla. I worked at Saks and Bergdorf Goodman for three years. The clientele was different, but the body insecurities were the same. That’s when I knew — it wasn’t about the bra itself. I could change someone’s life more meaningfully with a $60 bra than a $300 one.
Now, mind you, I was still trying to be on Broadway, and I took a job with Just Cavalli, which had just opened a big flagship store on Fifth Avenue. A friend worked there—it paid really well, it was prestigious, and I thought, "How fancy!" But I was miserable.
It was right before the 2008 recession hit, and I realized something huge: everybody has their own sharp tool for transformation. For some, it’s clothes, but for me, clothing felt like a blunt tool. So, when they let me go—along with so many others—I was devastated for about three days…and then I was relieved.
I spent the next eight months unemployed, figuring out what I really wanted. I dabbled in creative work, commercials, and even worked on a Martha Stewart craft show. And then, the original bra shop called me back. It was humbling—I went from making over $65K a year to $12 an hour—but I said yes. That role led me to become their store manager, then their trainer, then their marketing manager, and eventually their marketing director.
Not because I had a marketing degree, but because I knew our customer so well—and I cared.
It became really exciting for me to create educational content—not just for one person in the fitting room, but content that could reach thousands, even millions. This was right when social media started booming around 2010–2011, and it was life-altering to realize how much impact I could make.
So in 2014, I started my own business. Over 10 years later, I’m still running it, under the same name I came up with in college—as a joke. You never know where a name will take you. People think I’m still a bra fitter—which I rarely do now. What I really do is run a media and educational content company. I train people, I educate, and I help brands share their products with the world through impactful content. That’s what I do now.
The Power of Lingerie
Micki:
Your journey is so amazing. I’ve also been asked “why undergarments?” I could create any product, so, why this? There was so much for me in my connection to undergarments. Coming in from the ballet world where my body was never the “perfect ballet body.” I had curves. I was tiny, but I had curves. And so body image was always something I really struggled with. There was something about putting on undergarments that fit me well and that I felt beautiful in, that was really transformative.
Kimmay:
Absolutely. Bras and underwear cover such sacred parts of the body. And when you put on something that fits great, feels amazing, and is matched with your values and looks fantastic, it changes your whole day. Let's say you do that every single day for one year, that 1% change can totally shift your trajectory from feeling “ugh” to feeling great.
In the fitting room, I often see people dealing with three big things: discomfort, shame, and confusion. Discomfort is easy—digging straps, riding bands. But shame shows up too, especially around cup size. The stories we carry—too much, not enough—are deeply ingrained. And confusion? Most people don’t know how a bra should actually fit. We’re passing down guesses from our mothers and grandmothers, without real education.
The reason I work in undergarments is because I do think we can change the world. Because when you feel that way within yourself you are more open to being loving with other people. You are more open to being understanding with other people. You have more capacity, when you take care of yourself, to take care of others. And that's our biggest purpose in the world.
Kimmay in London. Photo by Scandi Sisters.
More Than Your Numbers
Micki:
You mentioned the things that come up in the fitting room, and cup size being one—and all the baggage that comes with that. This is so true, not just with bra sizing, but with sizing in general. The size jeans you wear, the size shirt you wear. Then you have so many brands in the marketplace doing different things, so then we as consumers, maybe are putting on a small in one brand, and then putting on a medium, or a 32C in one brand, and then a 34D in another. How do you navigate that with people?
Kimmay:
Wow, I love this question. Sizing is such a fabulous topic for me because it is so potent. For some clients, when I'm fitting them we don't discuss numbers. Numbers are not a healthy place for them to discuss, right? And that might be true for many numbers. For them, it might be weight, it might be their age, it might be their salary, it might be their bra size. And when we measure someone, you can feel what someone's feeling. You can really witness when it’s safe to share numbers with the person and when it’s not. There's power in in both ways, but I really encourage people, when possible, to use numbers as information and not a definition of who you are. And so that's an education point for me in the fitting room every time.
This is the reason I created this campaign called More Than My Numbers, which I started in 2015 because nobody else wanted to produce it. Because every single time I would wrap the measuring tape around someone, what do you think happened? They would immediately try to get smaller and hold in their breath. And then they would also be like, “so, what am I?”
Number one, this measurement is only going to give us a starting point.You can wear nine different bra sizes depending on the sizing method somebody uses, or what country it's made in the firmness of the elastic, etc. Everything changes depending on many factors. But also, I was like, can you just breathe like a human. This is not who you are. Who you are is a divinely created, generous, beautiful inside, outside and underneath person, you're not a number, like, that's not actually who you are. And if I put this number next to you, it would tell us, like, very little about who you actually are.
This number can also change. Come to me in three months, come to me in three years, come to me after three babies, like, your body's going to be different. That size can change. There are certain things about you that will never change, including your worth, which is immeasurable,
So I created a whole campaign that now has been going global for years and years and years. I kind of can't get away from it. I kept thinking, maybe that was good for a time, and and then it just keeps coming up. People love this campaign.
Inside, Outside, and Underneath
Micki:
You have a beautiful mantra: Inside, Outside and Underneath. Can you speak a bit more to the meaning behind it?
Kimmay:
Typically I say I help people say “hooray, inside, outside and underneath.” My tendency to start coaching people in the fitting room comes from the belief that we have to start inside. That’s where the real work happens. And by inside, I mean the way we talk to ourselves, our inner dialog, our faith, our purpose in the world, our values. That's all happening within us, and that includes those, what I call “I am”, statements of who you are—no matter what. Uncovering that and standing firm in that, and your purpose and your mission and your values is really who you are. It's your character. It's like your soul. That is the uncovering part that is the most important.
Outside means our relationship with other people around us, our work in the world, how we show up to the world. Even your clothes and how people see you. But I think a lot of people miss the underneath part, which is our physical bodies and what's underneath our clothes. Our bodies are tactile, and they are slower, so it takes them longer to understand something, and when, when somebody says, Wow, you really embody this, that's very different than just mentally getting something, when you walk it, when you live it, when you put your your body, into that work and into that practice. It's very different than just doing mindset work and then hoping it translates into the outside. So I like to work with people from the inside out.
Entrepreneurship
Kimmay:
This wasn’t the plan. I didn’t grow up dreaming of fitting people for bras and changing lives. But I think it's so important—a thing most people hate wearing or think is a torture device—I'm like, can we actually change that? But sometimes, you get very forcefully pushed into your purpose—whether you like it or not. And I think that’s beautiful. Some of the most unexpected journeys can become the most meaningful.
Micki:
I don't think that even five years ago, I would have had any idea that I would start a lingerie brand. It's definitely been a hard journey. And, I’m also so thrilled to be on this journey.
Kimmay:
I'm so proud of you. I could cry. The work that I'm doing is very much focused on the person and the work within the fitting room. But I'm not a designer. I'm not breathing life into products, and we need people like you who are doing that thoughtful, emotional work all the way back at the creation part of the product. So I'm really proud of you.
Micki:
As someone who’s often figuring this out alone, it can be a very lonely journey. I think about how hard it was to be a professional dancer. People would say, “If you made it through that, you can do anything.” But this journey is hard—some days it feels insanely insurmountable.
Kimmay:
We all have those days as business owners—where we wonder, “Why am I doing this?” I could be making more money working for someone else, with better health benefits. It’s hard to wear all the hats and be the boss and carry everything. And then, just when I think maybe I should throw my hat in, someone reaches out and says, “Thank you for the work you’re doing,” and I’m like—gosh darn it, here I am, back in the game.
So I hope I can be that person for you. Because this work needs you.
Micki:
Thank you. Yes, on the days that get really hard, something always happens—like the universe is literally saying, “Not yet. You can’t quit.”
Where to Find Kimmay
Micki:
Kimmay, this has been so inspiring. Where can people find you and learn more?
Kimmay:
If you want a free, empathetic fit guide, I have a great one over at HurrayKimmay.com/freefit. I’m also on every platform @HurrayKimmay. So come over and see me. I love to hang out on Instagram. It's my fave. If you read this and you want to come say hi, and either you got something from this that you're like, “Wow, that was really important for me to hear,” or you have a question, please, literally come over and ask me a question. Slide into my DMs. I can't guarantee I'm getting back to you right away, but I'd love to hear from you and let me know that you read about me on Micki’s Substack
Micki:
Thank you so much, Kimmay. Your wisdom is a gift, and I’m so grateful to have you in my corner.
