Your favorite Undergarment Educator and expert bra fitter (moi!) is back on The Drew Barrymore Show for more bra makeovers! These two had Drew, Valerie Bertinelli and I, plus the whole audience in tears of joy. I always say that I couldn’t do a regular bra fitting if I tried. Once we’re “in there”, I’ll get you a bra that fits and feels great, sure. But we’re also going to talk about your beliefs, your body image, and that sacred area just under the bra: your heart. In short, I’m going to help you say hurray inside, outside, and underneath. Hurray!

I have been preparing for 20 years for this kind of work, and it’s truly a blessing to share my own heart and expertise on TV and with you! Below I’m sharing the scoop on these two amazing makeovers – including an empowering and healing step after breast cancer, and a brand new lease on life after years of ill fitting bras – plus shop the styles they went home with and bonus styles for you to try out yourself. 

Remember: your body as it is today deserves the time and effort and money it takes to support and adorn yourself with kindness, honesty, and comfort. You got this and my hands are at your back. Dive in!

The Rack Shack and the brands and bra styles shared on the show were not partners, and were chosen organically as the best fit for each volunteer. Below you might find an affiliate link to one or more, including bonus styles we didn’t get to on air. As always, I only share styles I know are great for those I fit, and that I think will support you, too!

How to Put On Your Bra Without Ruining It

One thing that always fascinates me is how habitual the act of putting on your bra becomes. Oftentimes when I ask folks “so how do you put on your bra” they have to really think about it, because on a day to day basis they don’t think about it at all. They just do it. And what’s more, they think the way they do it is how everyone does it. But there are many “right” and “wrong” ways to put on your bra! I put “right” and “wrong” in quotes because you can put on your bra however you can or want to. Truly! But if you want your bra to last longer, there are a few methods that are better for the bra. In fact, the “crush and flip” that Valerie demonstrated on the show (and that my mom taught me, bless her) is a major reason that cups get dented, bands stretch out, and underwires pop free. So if you want to see some of the suggested methods I shared on the show, click the buttons below! I have a few video tutorials (including one video that went viral to 11 million views and counting!) to help you. It’s never too late to learn!

Check out the replay of the show (if and when it’s available) on Drew Barrymore.

Finally Finding a Bra That Fits

Amanda is a ball of energy… wearing worn out bras. The funny thing, though, is that she found out from the audience of The Drew Barrymore Show the last time I was on! As I taught about how tight the band should be, how snug the straps should fit, and what makes a well fitting cup, she realized really quickly: none of my bras fit. 

I was so excited to support her because she had just been making due with ill fitting bras for far too long. In fact, as an attempt to get more lift, she even resorted to filling her bra cups with paper towels. I mean, we do what we gotta do, right? On top of that, she recently lost her grandmother, and I could just see her powerful and sassy legacy living on in her granddaughter, as she made an empowered decision to support and adorn her body. Hurray!

So I was pleased to help her find a bra that fit well, lifted her bust, and even a great accessory to even things out (see below in the bra balancer section!) without the use of kitchen items. The plunge style of this bra and the inner cups gave her the lift and shape she wanted, while the back was smooth and sleek for her outfits. Doesn’t she look amazing?! And she FEELS amazing, too, which is what really matters. 

Shop the style she wore on the show below, as well as a few other options so you can find your own hurray. 

Chantelle – Norah Chic Plunge

T-Shirt Bra

• Chic and sheer graphic print lace over lightweight, plunge contour cups
• Super soft back with 4 hooks and eyes, plus enclosed seams for a smooth look
• Fully adjustable straps with a movable J hook for different wardrobe needs
• Eco-friendly fit and recycle materials, OEKO-TEX® Standard 100 certified
• Designed in France for style, with North American practicality in mind
• 30-38 bands, B-H Euro Cups
• Buy it at your local shop, or on Amazon

Beautiful Bras After Breast Cancer

Saying hurray for lingerie is more than just finding a good fit or a sassy style, it can be healing. That was the case for Caitlin, who came to our fitting after 2 ½ years of surgeries due to breast cancer. After a stage 4 diagnosis, she underwent a mastectomy and reconstruction on one side, and two reduction surgeries on the other. She also finally had a new nipple replaced onto her breast! After all that, she was finally ready to let go of the stretchy, post surgical bras and embrace beauty right over her heart again. 

Since she’d been cleared to wear underwires, we opted for a wired bra that would help support and shape her bust equally. I also for one with a plunge front and low center gore which did not interfere with her breasts, which are slightly more connected up top. This is common after surgeries, and the low plunge was a great shape for her bust. 

Additionally, she loved a bra balancer I had on hand (see below!) and this outrageous purple color gave her all the confidence! Wearing beautiful, well fitting bras right over the heart is truly part of the healing process, and Caitlin wore this one SO well. 

Shop the style she wore on the show, plus a few similar bra styles below. 

Gossard – Superboost Lace Plunge Bra

• Underwire bra made of stretch lace with a special inner sling on all sizes for an extra boost & projection
• Plunge front has a lower center gore that both reveals and doesn’t interfere with connected breast shapes 
• Cut and sew style features seams for support and shape
• Smaller sizes have 1 hook & eye row while medium to large sizes have 2 hook & eye rows
• This group comes in fun colors and various silhouettes 
• Oeko-Tex Standard 100
• Band sizes 30-38, B-G UK Cups
• Get fit for this at your local bra boutique, or shop other colors on Amazon

Free Fit Guide & Video

Want to wear a bra without ripping it off at the end of the day? Watch Kimmay’s video tutorial on getting a comfortable fit, plus a printable guide and checklist to take shopping. Don't spend another minute feeling uncomfortable in your bra.

Bra Balancers & Inserts to Even Out Breast Size and Shape

On my previous appearance on DREW, I discovered that Valerie Bertinelli has uneven breasts – a very common and normal thing that a lot of folks deal with. But what shocked me most was that she was using an old shoulder pad from the 1980’s to even things out. While this is resourceful, it’s probably not as useful as items made specifically for this! 

So I called up my friends at Evenly and brought a few styles for her to try out, and lovingly “bequeathed” one to her. She was so happy, and actually went home with two different styles and sizes to play with. Hurray! 

In addition to to Valerie, BOTH of our bra makeover volunteers went home with bra balancers. Amanda had naturally uneven breasts so I gifted her a small balancer to use to increase the volume on one side if she wanted to. She loved it! On the other hand, Caitlin had been through several breast surgeries and it left her reconstructed side and the side that underwent two reduction sides looking uneven. Wearing an underwire bra actually helped even out the silhouette, but she was still self-conscious about the lumpier texture on the reconstructed side. This is super common, so I chose a slim balancer that she placed in the front to even out the texture. She was thrilled! 

Whether you want to even out your bust shape, size, or texture these items can support you!  

If you’re tired of flimsy inserts that move around, I found a game-changing solution. Read my article on Honey Cloudz below.

Thank You & Boutique Support

I have to send a huge thank you to Drew Barrymore and her incredible team—again! Not only for creating space for real conversations about breasts, chests, and confidence, but for embracing my educational approach with such enthusiasm. It means the world to have this platform to show how a bra fitting can be more than just about undergarments—it’s a powerful coaching tool for self-worth and comfort.

A huge shoutout as well to The Rack Shack in Brooklyn, where we filmed part of the segment, and shopped for the bras shared on the show. Laura and her team welcomed us with open arms, letting us explore their beautifully curated bra selection. I specifically chose this woman-owned, size-inclusive boutique over a big department store because I knew they share my dedication to fit, support, and helping folks feel amazing. Amanda and Caitlin (my fabulous bra-fitting guests) walked away with more than just a better fit—they got a fresh start with their bra wardrobes and a whole new perspective on comfort.

If you’ve never had a professional fitting, let this be your sign: find a great boutique, work with a pro, and get the support you deserve. More info below to help you. Hurray!

Your turn: What’s your biggest worry about bras? How do you want to feel when you wear one? Did you catch the show? Share with me @hurraykimmay on Instagram!