The Art of Bra-Fitting

It is no secret that finding the right lingerie can boost confidence. But what’s even more important? Making sure that everything fits perfectly. Finding the right size and fit of a bra can be challenging – different band sizes, cup sizes, styles, fabrics, and cuts make every bra unique. In our attempt to unpack the art of bra-fitting, we spoke with Kimmay Caldwell, a bra fitting expert that’s been in the industry for over 10 years.

Kimmay began her career in the industry at a bra-fitting store in SoHo, and was immediately overwhelmed with the importance of finding the right fit. Kimmay found inspiration in the individuals that she assisted. She noticed that everyone who came into the shop – from supermodels to mothers -- had something negative to say about their body. From this inspiration, Kimmay created #MoreThanMyNumbers, and dove headfirst into the world of expert bra-fitting. In Kimmay’s words: “Size is a number. While it's important information to know and understand, the most important factor is fit. In fact, through the #MoreThanMyNumbers campaign I encourage people to use bra measurements and size (along with other numbers) as information, not a definition. When people say "I am a 34B", I lovingly offer up a correction. They are not a number or size. They are so much more! Knowing one's measurements and bra size starting points can help them narrow down the sizes with which to start in the fitting room. Then it's up to them and their fitter to assess the fit, comfort, and style for that individual.”

Now, Kimmay Caldwell is a bra industry expert with over a decade of experience since 2005. Her vast knowledge spans from bra fitting cup sizes AA-N, retail and e-commerce, marketing, content creation, buying and wholesale, and more. Her multifaceted background in the industry has made her a valuable ally for brands who aim to share their products with an authentic and empowering message. You may have seen her on The Today Show, The Rachael Ray Show, or The Martha Stewart Show, to name a few.

From our conversation with Kimmay, we have compiled a list of tips and tricks to help you find bras in the correct sizes – the trick to being comfortable and confident every day.

First, you must find your ‘starting points.’ These are the two simple measurements that will give you an approximate idea of your bra size. You should first measure your Bust – or the width around the widest part of your chest, in inches. Then you should measure your Underbust – the width around your ribs, just underneath your bust, and round up to the nearest even number of inches. With these two numbers, you can find an approximate cup size. Subtract the Underbust measurement from the Bust measurement, and match this number with the prospective cup (1=A, 2=B, 3=C, etc.) In the words of Kimmay, “Numbers are information, not a definition.” Because of the variation within bra sizing and fluctuation of the natural body, these two measurements cannot give you a consistently accurate size value. However, they give you a good starting point to begin your journey to finding bras that fit.

“Once you've measured and calculated your bra size starting points, or a fitter has helped you do so, it's time to try on each bra. It's nearly impossible to buy bras from different companies or countries, or made with different materials and designs, to each fit in the same size. Because size is a number, it doesn't tell the how story. I wrote a popular blog post on how 9 bra sizes can all fit based on material, country, sizing method, and more. The important thing is to assess the fit of each bra on your actual body, by yourself or with the support of a fitter. Without doing so, you're guessing that the fit will be a match for you based on numbers alone.” – Kimmay Caldwell

Next, you must find your sister sizes. According to Kimmay, “Sister sizing is the idea that bras are sized with the cup size relative to the band size. For example, a 36B and 38A have a different band size and the same cup size volume. Understanding this concept can help people discover a similar (but different) size when adjusting their bra choice based on fit feedback. When I share this as part of Bra 101 information on TV or in a magazine I'm always shocked at how many people have not heard of this concept. I often get emails thanking me for describing this or helping them realize why the 38B they tried on had a bigger cup than the 36B they had been wearing. Understanding how sister sizing works is key for being able to adjust sizes and get a really great, supportive fit.”

The concept of sister sizing is not well-known by the average consumer, but can help immensely when finding a bra that fits. Sister Sizing represents the size relationship between bands and cups. As a bra’s band size changes, the cup size adjusts accordingly. This means, as you adjust the width of the band to find the right fit, you will also have to adjust the cup size. Using your ‘starting point’ numbers, you can find sister sizes that are likely to fit similarly. According to Kimmay, “the basic rule to remember is ‘up in the band, down in the cup or ‘down in the band, up in the cup’ to keep the same cup size volume.” However, it is essential to remember that these sizes do not guarantee fit.

So, what’s the most important part of finding a bra that fits? Trial and error. Every bra fits differently – based on band size, cup size, fabric, cut, and style. Finding your ‘starting point’ measurements and ‘sister sizes’ can be a great first step, but trying everything on is the real key to finding bras that fit perfectlyThis process can help you understand your own body and its needs. It can increase confidence, comfort, and support on a physical and emotional level. And last, but not least, it can give you a slick foundation to create all of your desired clothing looks.

“I have fit thousands of people for bras and have seen their lives shift in simple and dramatic ways.” – Kimmay Caldwell

For a collection of resources from Kimmay, visit

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