I’ve been in the bra fitting industry for almost 20 years, and as an Undergarment Educator I’ve gotten a lot of questions through those years. Thanks to Hoda & Jenna and the folks at The Today Show, I was able to answer a few of the biggest bra, fit, and size questions. Below are the answers to questions about finding your best bra size, learning how your bra should fit (finally), nipple coverage (and enhancer!) options, and how to even out bust difference. 

In the end, my goal is to help you make a loving and informed decision about what you wear right over your heart. I truly believe that wearing bras that fit well and feel great leads to greater confidence and comfort. And whether you’ve been wearing bras for 4 or 40 years, it’s never too late to learn something new. Let’s get to it. Hurray!

Psst! Some of the brands linked here might be past or future partners of mine, but were independently chosen for this segment without compensation or contract. I’m proud to bring them your way! As always, I share what I think will support you and help you say hurray.

Watch the recap video clip on the Today Show website!

Comfort & Confidence from Bras That Fit

One of the best ways to say hurray is a well fitting bra. I know, I know hear me out! If you have a hate hate relationship with your bra, you’re not alone. But that’s because most of us weren’t taught how to shop for bras, pick the best size, or how to determine if it even fits. That’s why I’m on a mission to educate and inspire bra wearers everywhere. Because, just like shoes, wearing the wrong size or style for your unique body will hurt. That means even the best bra in the wrong size will feel like a bad bra! So along with some of the best bra options below, pay attention to my tips in the segment for getting a great fit. And don’t forget to go to your local bra fitting shop for support from a professional. 

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Question: How do I know if I’m in the right bra size? 

Answer: Dalena has been wearing bras for years, but still isn’t sure if she’s in the right size or fit. Sound familiar? In my years as a bra fitter, the most common age was in their 50s, and nearly every one was still off the mark with their size and uncomfortable in their bra. Luckily, it’s never too late to learn! 

The truth is, bra sizes and fit vary depending on the brand, cut, coverage, and material. So, it’s important to take your measurements or work with a professional fitter to find the best sizes to start with. Then, you can compare the fit between each and adjust the size as needed. 

In Delena’s case, she thought a 34A would fit her best, but the gapping cups weren’t caused from a too big cup, but from a too big band, and loose straps. In the end, I changed her size to 30D and 32C and sent her home with a bra wardrobe that fits flush against her skin, hugs her body, stays in place, and feels good. Hurray!

Want to feel as good as Dalena? Below are two of my top resources to support your journey of finding the bra sizes and fit that’s best for you. 

Buy & Try the bras from the show:

Question: How can I stop my bra band from riding up all day? 

Answer: Most people I’ve fit are wearing a bra band that is way too big. In clothing, we think of loose for comfort, but bras should fit like a great pair of leggings. Snug enough to stay in place without falling down, or digging in. Kerin is wearing a stretchy bra with a band size that’s way too big. Many folks do this in order to get a fuller cup size, but then her bust just pulls everything down in the front, hiking the band up in the back. The best way to keep your band from riding up is to get a bra band that fits snug like a hug. And because 90% of the bra’s support comes from the band, and every other part of the bra’s fit relies on the band, you’ll be several steps closer to a bra that fits and feels great. 

Kerin went from a 40DDD or XL larger to a UK 36HH (which is a US 36L!) That snug band, full cup, underwire, and seams means she can walk around supported and feeling awesome. You can, too.

Also, keep in mind that bodies change, and bras stretch out. So if you were wearing a bra that fit at one point, check in on the band and make sure you adjust it as it stretches out. For that reason, I usually suggest buying a new bra that fits on the loosest hook. That way you’ll have plenty of room to move in as it stretches out over time. 

Buy & Try the bras from the show:

Question: How can I fit uneven breasts?

Answer: Uneven breasts are so common. SO common. Just like hands and feet, breasts are never perfectly symmetrical. And some vary in size more than others. Always, make sure you fit your bra to the fullest cup. That way you can leave a little bit of room or add in something to the smaller side, rather than fit to the smaller side and dig in or spill out of the fuller side. 

If you have a small difference, a simple stretch cup can help your bra flex to fit both without gapping. For larger differences, you can fill the smaller side with an insert or balancer. There are many sizes available and it’s easier than ever to even out your silhouette. In fact, you can even buy a bra that connects to provide one cup size on one side, and another on the other side. Genius! In the end, know that your body is beautiful, and there are many options to fit your bust as it is, or even things out if you want to. Hurray! 

Buy & Try the bras from the show:

Question: How can I conceal or enhance my nipple?

Answer: Honestly, one of the most common reasons people wear bras in North America is for modesty, and to conceal nipples. That said, you can wear a contour cup to do so, or you can pop on some reusable nipple covers. These work great with or without a bra and can turn your favorite sheer bra into a more modest option. Want something more fun than an invisible skin tone option? Decorate your bust with stick on flowers or pretty colors! It’s up to you.

Or, you might want to enhance your nipple! While nipple bras like the one from Skimms have existed for years (there was a popular one in the 1970s), nipple enhancers are a really beautiful option for folks after breast cancer surgery. Reconstructed breast tissue does not include a nipple, and that can often feel really jarring when looking in the mirror. So much of our identity and womanhood can be found in our bust, and this is a simple way for some folks to achieve a look that feels most like themselves. 

You get to decide how you shape your bust, and if you conceal or enhance your nipples. As the decider of your body, it’s up to you!

Buy & Try the bras from the show:

Buy & Try the bras from the show:

Need more support?

Free Bra Class

Want to wear a bra without ripping it off at the end of the day? Watch How to Find a Comfortable Bra Fit For Your Body WITHOUT Wasting Your Money on Bras You Dread Wearing! Plus, you'll also get Kimmay's Bra Fit Guide, and a taste of Bra Confidence & Comfort™. Watch now and don't spend another minute feeling uncomfortable in your bra.

Your turn: What questions do you have about bras? Were any of yours answered here? Share it all with me over @hurraykimmay on Instagram!

Credits:​ Thanks to the volunteers, and Today Show staff and crew (and amazing producers)! And a special thank you to the brands that helped make this happen.