Kim "Kimmay" Caldwell

Kimmay Caldwell of Hurray Kimmay lingerie writer and expert bra fitter
Kimmay Caldwell, lingerie writer and bra fitting expert of Hurray Kimmay. Hurray Kimmay/Own Your Sexy


Hurray! My name is Kim, and you can call me Kimmay. I’m the owner of Hurray Media. And my business all started with boobs.

I started my career in the lingerie industry as a bra fitter in January of 2005, when I was putting myself through college in New York City. That’s quite a few years and busts ago. Since then, I’ve worked in a small family-owned shop, for large department stores, and for one of the most luxurious brands on the planet. I’ve helped educate and inspire women with AA-N cup sizes. I’ve sold a $5 panty and a $575 bra. I’ve appeared on shows like Tim Gunn’s Guide to Style, The Martha Stewart Show, and The Rachael Ray Show sharing my swimwear and undergarment expertise. I’ve also been quoted in magazines like Real Simple, Women’s Health, Brides, and more. You may have even seen me in a national bra commercial, or wearing my bathing suit in O Magazine. I’ve literally helped thousands of people find their comfort and confidence in the bra fitting room, and beyond. I have a long history of writing about lingerie and providing advice. It's my passion and my purpose to share it with you! 


I started my career in lingerie as a bra fitter way back in January 2005. I have fit women into bras ranging from AA-N cup, swimwear, loungewear, lingerie, post-surgical products, nursing items, and more. In the bra fitting rooms, I have helped thousands of customers! 

I’ve witnessed a lot of confusion in these fitting rooms. I feel so fortunate to have helped clients walk out of a bra fitting appointment feeling confident and comfortable. I truly believe that a bra fitting can change a woman's life, and she can go on to change the world. Plus, I simply adore lingerie and the wonderful way it can make us feel.

Behind the scenes, I’ve worked closely with the Saks Fifth Avenue and Linda’s buying department, giving me a unique view into buyer’s insight. I’ve assisted in wholesale and market week with La Perla, I’ve sold luxury lingerie brands at CurveNY (the big lingerie trade show), showing several lines at once. I have a rare mixture of wholesale, retail, sales, marketing, and 

Now I have my own website, Hurray Kimmay, with resources to help women say hurray inside, outside, and underneath - including bra fittings, women's circles, and articles. I also run a content marketing company called, Hurray Media. My all female team and I create educational and inspriational content for some of the most wonderful lingerie and swimsuit brands in the industry.


I graduated from Marymount Manhattan College in New York City with a degree in Theater and a minor in Musical Theater. 

I use my performance education as a tool in my marketing and literary career. I sit on the board and in the soprano section of The Astoria Choir in Queens, NY. In addition, I am proud member of several entrepreneur courses and communities including Marie Forleo's B-School and Natalie MacNeil's Conquer Club. 

A Message from Kim "Kimmay" Caldwell

 Lingerie is my favorite way to say hurray on the inside, outside, and underneath™

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