Ask An Expert

Ask An Expert

Who is Kim?

Professional bra-fitter and lingerie expert Kim Caldwell is here to quell your buying fears and give you the encouragement you need to say “hurray” about your body. In addition to running her own successful blog and consulting company, Kim is the lingerie expert for, has appeared on The Martha Stewart Show and Tim Gunn’s Guide to Style and many more, all while working tirelessly to bring awareness and comfort to both millennial women and baby boomers about their undergarments. “I truly believe that a well fitting bra can help a woman stand tall, lead with her heart, and say hurray,” proclaims Kim. We say hurray for Kim!

How She Began Her Journey

Kim attributes much of her success to her motto, “Be nice and show up”,  a mantra she’s practice since she worked in a small shop in NYC selling lingerie while earning her degree in Theater from Marymount Manhattan College. Kim was quickly recruited by a rep from Saks 5th Avenue and then by another to sell La Perla, where she soaked up all the knowledge she could in the world of lingerie and bra-fitting before becoming the brand merchandiser at Bergdorf Goodman.

The recession of 2007-2008 took a toll on her and she lost her big corporate job; going back to a small shop, climbing from employee all the way to marketing director —she knew her customers and their pain points so well that she was able to reach women directly and on a personal level. Her boss there was actually the one to give her the idea to start her own company as a bra-fitting consultant. “I could sell lingerie with my hands behind my back with my eyes closed,” she ruminates. “It just made sense to branch out on my own now that I’ve had so much experience with both lingerie and marketing.” Now, she makes videos, social media, blog post content, and other marketing for mostly smaller companies but she has a plethora of clients in her bra-fitting and consulting portfolio.

Owning Her Style

As you can imagine, Kim owns over 100 bras, and well over 200 pairs of underwear. As for fashion “on the outside”, she tells us one of her favorite things about being a woman is having permission to be expressive all the time —especially in New York City! “Today I’m in a tank and flannel, dark jeans and some riding boots and glasses. Yesterday I wore a high, black turtleneck and necklace. It’s whatever I feel like that day!” she beams.

Kimmay Looks Comfortable In A T-Shirt, Jeans, Flip Flops and Comfy Sweater

Kimmay Looks Comfortable In A T-Shirt, Jeans, Flip Flops and Comfy Sweater

Kim wasn’t always so liberated, though, as she used to feel immense pressure to wear more dramatic outfits for press events. She laughs as she describes her ensemble for her first press gig while working for La Perla, Live on NBC on The Martha Stewart Show: “All La Perla styles, a low-cut, high-slit dress, big heels, thigh highs, and the huge ball of nerves in my stomach!” After that, she was a guest on Tim Gunn’s Guide to Style and has steadily guested on many, many shows as a professional bra fitter, her style evolving as she becomes more comfortable with her own body.

Cup Size Stigmas

Kim tells us 90% of the women that would come in wearing an ill-fitting bra didn’t realize that once you go down in band size you must go up in cup size —a fact which bothers many women based on decades-old stigmas. Kim has done a lot of “unscientific research” asking women what cup sizes mean to them, and the results are fascinating:

“A size – sporty, smart, plain, not very sexy, serious, thin.

B-C size – just right, average, nothing special, basic.

D-DD – big boobed, sexy, slutty, or loose.

DDD+ – sloppy, a mess, voluptuous, or a pin-up.”

“Crazy right?” she says in dismay. We can relate to this frustration, which is why we offer our styles in sizes XS through 16-18 — not an arbitrary letter that could mean anything — sticking true to US Standard sizes to mitigate the fear women have when purchasing a larger size.

Addressing The Issue

Kim practices what she preaches about loving our bodies; she doesn’t Photoshop her pictures and asks companies that sponsor her to follow suit. Her garments always fit, and she once tried on 9 bras from different brands in various sizes that all fit perfectly. We asked Kim if she had plans to start her own line of bras to combat this strange sizing phenomenon and while she neither confirmed nor denied, she did tell us standard sizing is a huge issue for her. “Transparency with measurements is the way to go,” she explains. “And I’d definitely be open to maybe doing a line with another company that I felt embraced my values about how we view our bodies.” We would definitely buy a bra from her line — she’s an expert.

Kimmay Wearing a Montelle Bra and Fleurt Robe in Nourish

Kimmay Wearing a Montelle Bra and Fleurt Robe in Nourish

The Best T-Shirt Bras

While we at Stepforward support women with our carefully crafted clothing on the outside, Kim advised us on how to support women from underneath. She tells us that the biggest stipulation for a t-shirt bra is that it’s smooth underneath the t-shirt, which is the most sought-after quality in bras in the US right now. “Breasts are accessories and how you shape them is up to you!” she tells us. The most traditional style is molded (when you lay it down it keeps its shape), with underwire, smooth, slightly separated, and in neutral colors. Below are the bras she thinks are the best for wearing under t-shirts, like perhaps even under a Stepforward scoop or v-neck!

The Best T-Shirt Bras, According To Kim: Wacoal, Anita, Ongossamer, Natori, Le Mystere, Simone Perele

The Best T-Shirt Bras, According To Kim

Kim’s Inspiration

In business, Kim admires a few lady entrepreneurs who are “killing it and run their businesses in a way that is heart-led and smart and forward-thinking.” She admires Marie Forleo, Kris Carr, Gabrielle Bernstein, Mamagenas, Danielle Laporte, Natalie MacNeil — women who are making a business out of doing what their heart is leading them to do. She’s in Natalie’s Conquer Club and as part of her business plan they do meditations and tap into their hearts to ask what the world needs. We’re all in this together, empowering women to accept their minds and bodies and push through stereotypes to keep moving forward in a supportive arena.

What’s next?

Kim is embracing her ever-changing body as she enters the next phase of her life. “What happens when age and pregnancy or possibly even disease changes it?” she laments, anxious yet excited for what the future holds. We will be tagging along for her journey, and you can follow Kim on Instagram, Twitter, and Facebook and check her website for an incredible amount of content related to all things celebrating our bodies. Be sure to check out her Top 5 bra-fitting tips and opt-in to her newsletter stay up-to-date on how to say “hurray” to your own body and outfit yourself in undergarments that work for you.Save


Jesse Erin