This Friday we chat with Kimmay Caldwell, a multi-tasker par extraordinaire: bra fitter, media owner and media personality and educator – her vast experience and knowledge spans from bra fitting cup sizes AA-N, retail and e-commerce, marketing and content creation, buying and wholesale, and much more. Based in the USA her influence and expertise extends across the pond and her exuberance and joie de vivre have won her followers and fans across the world. We can only say Hurray Kimmay!
Life before Hurray Kimmay?
I grew up in NY State and moved to New York City when I was 18 where I put myself through university while studying musical theatre. I didn’t come from a wealthy family. In fact, my parents split when I was just two and my mom had to lean on government assistance to help my older brothers and I through. Her resourcefulness and strength are embedded in me forever, and that got me through some really tough, poor times living in New York. I have been a singer and performer from when I was very young. And while I love being in the spotlight, I also had major struggles with insecurities and poor body image. In fact, taking a $10/hour bra fitting job when I was 20 years old changed my life. Not just because it paid more than the $7/hour I was making selling shoes, but because of how it opened my eyes to real bodies instead of the perfectly airbrushed images in magazines. It was a huge step in my devotion to talking kinder to myself, and using a bra fitting to help others do the same.
Your career before launching Hurray Kimmay?
I started Hurray Kimmay as a blog, and in 2014 I officially founded Hurray Media LLC and in the last 10 years it has expanded into an education, content creation, and coaching company with a global reach. Before this, I was a theatre actress and worked in retail. New York City retail is a beast – and I have worked in a small bra boutique in Soho, Saks Fifth Ave and Bergdorf Goodman, as well as for La Perla. I’ve even worked on the backend of an online bra company as their marketing director. I finally took the plunge to create my own company when a former producer for Tim Gunn’s Guide to Style, a show I had been on when working for La Perla 7 years earlier, came in for a bra fitting one day and encouraged me to dive in and go out and create my own thing. I have been in the business of bras since 2005!
Why fitting and coaching in intimate apparel?
I knew in an instant that I could absolutely serve folks in a major way with the right bra. But I knew I could also go deeper. While we were in the fitting room, why not discuss who you see in the mirror? Why not uncover some old stories and repair your relationship with yourself.
A secret: though I personally love bras and lingerie, I don’t actually care if anyone wears them. I truly don’t. What I do want is if someone chooses to wear a bra, that they make a loving and informed decision about what they wear right over their heart each day. Right over their heart! This part of the body is so rich with stories we’ve made up, expectations we’ve bought into, limitations on our own worth and beauty. And in an empathetic bra fitting we can undo those stories. We can look in the mirror and talk kinder to ourselves. We can support and adorn ourselves in a sacred area of ourselves. And, we get to repeat that ritual every day. That small daily action adds up! That ritual of supporting yourself and maybe saying something kind to yourself becomes habit, and habits change us. I have seen a bra fitting and then a daily choice to honour yourself and your body absolutely change people’s lives for the better. Now they are walking around with their shoulders back and hearts out and making heart led decisions. I mean it when I say that a bra fitting session (especially the way I do them) can change the world.
Bras just happen to be my sharpest tool to live out my why in the world.
What is different about the underwear market?
I often joke with newcomers to the industry, “Welcome, you’re never leaving.” Ha! The truth is that this industry is really special. We have such a unique opportunity to dress folks for their most intimate moments. Every side of the industry can feel that – from marketers to designers, and beyond. But my most rewarding and immediately impactful experience has been as a bra fitter. That’s why I now train fitters to fit with accuracy and empathy in The Fitters’ Formula. We need more experienced and heart led fitters providing transformation for more people.
How have you managed to increase your profile from USA to Europe and beyond?
I owe a lot of my reach to my networking and relationship skills, as well as my prolific content and social media presence. WOO, or “winning others over” is my stop Clifton Strength, and it along with a genuine curiosity and high work ethic have helped me immensely in building up relationships. I took a big risk in 2018 and went to Paris for the Salon International de la Lingerie show. There, and through Curve NY contacts, I met the team and they invited me to create a workshop on the show floor at the next show. I loved this workshop, and really hit it out of the park! Over the years it grew and grew. Attendees would tell me that they came to the show just for my workshop. Or they would tell me they wanted to be the “me” of their country. It was a wonderful way to cement myself as an expert, and get the word out about fitting with empathy in Europe. Now, I have an even bigger reach. The Fitters’ Formula, for example, has members from Iceland, France, Australia, Guatemala, Puerto Rico, Canada, USA, South Africa, and more. I’m so thankful for modern technology and big events that bring us all together!
A typical week?
I truly don’t have a typical week but here’s a try:
- Sunday: Church and a date with my honey (he loves history and we currently live in Philadelphia so there are plenty of opportunities for this)
- Monday: Usually a coaching client, then a meeting with my content manager who is currently based in Portugal pursuing her Masters
- Tuesday: Once a month we have a team meeting, then I have a newsletter and Fitter’s Formula content meeting with another team member, then a Creator’s group meeting I’m in
- Wednesday: I have a standing 2 hour co-working session with two fellow women in business (we’ve been doing this for something like 6 years), and this is a big writing day for me: newsletters, blogs, copy, etc plus meetings
- Thursday: Meeting with my online business manager, film 5-10 TikToks with my video manager, and then pitches and sales meetings
- Friday: this is my spill over day. I often have supportive meetings for my own business this day, or I meet with our IT person to build out our upcoming bra fitter directory, or catch up on work and calls. This is also a night I either crash or go out with friends to a museum or new restaurant.
- Saturday: Veg and/or a game night with my friends
Throughout those weeks I also have group coaching calls with my mentors, check in on my Fitters’ Formula group or host calls, answer press questions for magazines or get interviewed on a podcast, hold the vision for the business, pitch clients and have sales calls, and create content for any workshops or events I’m hosting. Of course, if I’m travelling or doing a TV segment, this all gets uprooted.
Who do you admire in the underwear industry?
Gosh! There are so many people I look up to and am grateful for!
One is Ivana Nonnis, who was the CEO for La Perla when I worked there. She is steadfast, and a class act, and has always believed in me, even back when I was in my early 20s. She was the first person to suggest me for TV, putting me on The Martha Stewart Show back in 2007 when I was just 22. It was LIVE on national TV and an experience that has led me to TV again and again.
I also think Sonya Perkins from Forever Yours is up there! She is so real, and so smart, and her longevity as a retail owner is absolutely astounding. She is also a major reason I created The Fitters’ Formula, and I am so grateful for both her encouragement (aka her demand!) and support.
I could write about hundreds of other people who I think are amazing but these two came to mind right away.
Any other ambitions for yourself and the Hurray Kimmay brand?
Any? Ha! I have many. Sometimes I find myself having to prune away my ambitions because I tend to work on too many things at once. I have a few that I’m actively working on, then I also have plenty of ideas that I think could be fun, and I’m not sure how or when they’ll really happen. Some of the latter include writing a book, creating empowering bra and body educational content for schools and young people (I’d love to partner with Michele Obama on this), and building a production company that focuses on matching brands with creators, and fitting influencers and models into bras and products that actually fit (nothing irks me more than when a social media brand ambassador or model is wearing a bra that doesn’t fit). At one point I thought I might like to become the go-to undergarment expert for TV and film, and work with celebrities. I’ve even dreamt of having my own TV show or magazine, or a regular segment or column in an existing publication.
Kimmay on The Marilyn Denis Show
Proudest/most exciting moment to date?
Some of my proudest are behind the scenes, and several have to do with saying no to projects. In the very beginning when I was in need of funds, a bra company asked me to work with them but their values and my values truly didn’t match up. I was tempted to give in, but it truly made me sick to my stomach and I knew I wouldn’t be able to sleep at night knowing I’d endorsed their products. I said I wasn’t a match for them and went on my way, unsure if I’d ever book a brand partner ever again. Turns out, I’ve now worked with over 100 amazing clients and did not need to neglect my integrity.
I also was awarded the very first Lingerie Influencer of the Year by Curve and NPD back in 2021. There are MANY amazing influencers in this space, so I was very honoured!
I’m also quite proud of my TV appearances on Rachael Ray (10), Marilyn Denis (13), and The Today Show (5). Mostly because TV is fun and exciting, but also so much work. I have to keep so many things in mind as I pitch the topic, write the talking points, pitch brands, secure volunteers, then fit them and calm their nerves, appease the producers and the legal team and the hosts, share complicated bra tips in bite sized versions, be fun and approachable and filled with energy, all early in the morning. Phew! It’s a lot. And, it’s also extremely rewarding.
And I would have to say doing photo shoots and hosting events in Paris does not get old. For someone who came from government assistance, and could barely pay her very meagre rent while putting herself through university, who hated her body and thought she was worthless, to then traveling to Paris 11 times and all over the world teaching empowering workshops, and encouraging people to love themselves…. That’s a hurray. Creating filter free photo content, especially stopping traffic in my underwear in front of the Eiffel Tower was definitely a highlight!
And regrets?
Other than putting my foot in my mouth a few times with something nerdy or stupid I said (we all have those), no not really. I’ve been through some pretty difficult things. But we all know how much those help us become who we are now. I like who I am now, so I’m thankful for the decisions I’ve made, and grateful that my integrity standards are very high. Sticking to my values, my why, and my integrity has never steered me wrong.
Sticking to my values, my why, and my integrity has never steered me wrong.
Where do you see yourself in 5-10 years’ time?
My husband and I have been trying to conceive for more than 3 years. I’ve been pretty public about our trials, so I truly hope in 5-10 years we’ll have two little ones! I have some global plans for my business, including growing The Fitters’ Formula and creating a wave of love that spreads worldwide… and I know how those things can change in a heartbeat. Ha! That said, I have seen both our children and my business in visions (almost like dreams) that feel like promises. So I am standing firm on those promises coming true.
How do you relax?
I sing! I love to sing worship music, especially, which keeps me reminded that I’m not alone while making these big moves in the world. I also sing while I cook – it’s my favourite thing. I’m a pretty anxious person so I find meditation and prayer extremely relaxing. I shop, I travel, I read. But I also love to watch TV and movies, I am a big bath person, and you can sign me up for a massage pretty much any moment of any day and I’ll say yes.
Pet Hate?
People who chew loudly or with their mouths open give me an absolute ick. To be fair, sometimes it is my husband. I have ushered him out of a room or put on headphones more than once. We wouldn’t have gotten to 18 years together otherwise.
@hurraykimmay
