Hurray! I’ve done a lot of bra makeovers on TV over my 20 years in the bra business. And as an Undergarment Educator, I truly relish the opportunity to speak to thousands or even millions at a time about how powerful and transformative wearing a bra that fits well and feels good can be. 

But this one was extra special. This was my first appearance and bra makeovers ever on The Drew Barrymore Show! To answer a few of your questions: 

• Yes, Drew Barrymore (and her crew!) are just as lovely as they seem 
• Yes, I’ve been on Today, Rachael Ray, and countless other major TV shows but meeting Drew (who is a bonafide movie star) was extra special and exciting
• Yes, when I booked this segment I ran around the room like an excited little girl
• And yes, we got to go deep and talk about things way beyond the bra such as why supporting your bust unlocks blocked energy so you can lead with your heart, a core value of mine. 

“Everything about this experience has been life alternating in the greatest way and I am so thankful” – Liza

Read on for the behind the scenes scoop on these two amazing bra makeovers on The Drew Barrymore Show, and see how I can support you! 

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!

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

Uneven Busts and Unexpected Sizes

My segment was part of their Breast Show Ever, a full hour dedicated to the chests and breasts of the world – and all of the issues, joys, and worries that come with owning them. Um, basically a match made in heaven. This is what I’ve been discussing for 20+ years! The moment I met her, I thanked Drew for opening up this conversation on TV. She is truly making a difference! 

In addition to Drew, 80’s TV star (and fabulous lady) Valerie Bertinelli was on hand to co-host the segment with her. I was able to give Val a very quick measurement check in order to assess her current bra fit backstage. She was wearing a great bra… in the wrong size. When we discussed how the 34C wasn’t the best option for her, she knew she might be due for a size update. But she was shocked when I said 30F (aka 30DDD) would fit best. 

Remember: bust size is relative to band size! So a 34C has the same cup size volume as 32D, or 30E (aka 30DD). So really we just went down two band sizes and up one cup size. It just sounds so different! 

She also has asymmetrical breasts which is SO common, and was using a 1980’s shoulder pad to even things out. I mean, you do what you got to do! Good news for Val, I have some options for this that do not require vintage fashion, including bra balancers. 

Finding the Best Bra Size

 Liza was a ball of energy and a woman on a mission with big plans this year – but her poorly fitting bras were holding her back. Like most bra wearers, she was wearing a cup size (or two!) too small and a band size too big. So we took this vivacious woman from 38C into a 36DDD in some bras. Yep! 

That size change alone completely changed how she looked and felt, and she definitely had some bra size shock. But it was the style, coverage, and shape adjustment that really helped her say hurray. As we age, breast tissue can become softer. Liza wanted to avoid spillage, so I found a bra for her that still showcased some cleavage but without the severe plunge. That way everyone stayed inside. 

One thing I’ve never forget about Liza was when we were trying on bonus styles and she slipped into a sexy lace bra. She said “Oh, my husband will love this!” and I said “Girl, this is for you.” Her eyes welled up with tears. So many of us forget that we are deserving of support, pleasure, and beauty whether anyone else sees it or not. I could see that her whole perspective was changed in one moment. 

“I am allowed as a woman to wear something just for me. Just to know I am allowed to do something empowering for myself and make myself feel better, it’s amazing.”

– Liza

Want to try the bra she wore on Drew? Check it out, plus several others that she loved that didn’t make it on air!

Natori – Elusive Full Fit Bra

• Full-coverage underwire bra with a seamless, molded design for a smooth silhouette
• Seamless stretch foam cups molded with power mesh for a supportive fit
• Soft, decorative lace detailing along the band and neckline adds an elegant touch without bulk
• Adjustable straps and back for a customized, comfortable fit
• Uses certified safe and high quality materials with OEKO-TEX® Standard 100
• Classic black color for versatility under any outfit
• Available in sizes 32-42 bands, US C-H cups 

Cup Size Isn’t Who You Are

Cassandra is tall, gorgeous, funny… and absolutely wrong about her bra size. It happens! And in this case, she has an idea in her mind that she was part of the “itty bitty” community, and only A cups would fit. 

I could tell that this wasn’t just a misunderstanding about her bra size, but also her identity. So often we associate bra size with our identity. We let our band and cup size “mean something” about us. Most commonly that we are too much or not enough, that we are beautiful or not, and that we are worthy or unworthy. Phew! 

So when I told Cassandra that the comfortable, supportive, and stunning strapless bra she was wearing was a 34D, and not the 36A that she usually wears, she was blown away. This kind of change can challenge or empower folks, and Cassandra chose (after the shock wore off) to take it in stride. 

Note: you can wear more than one bra size depending on the brand, material, shape, etc and in most bras she was fitting great into 34C. This strapless has a push up, and it’s common to size up 1 cup size for push up bras. Additionally, she measured for a 32 but her ribs flare outward a bit, and her bust isn’t very heavy, so we opted for the snug enough to stay in place 34 band over the more firm than we need it 32 band. 

“I hope everyone can have this experience, no matter how old or how young you are.” – Cassandra

More important than the size adjustment was her energy adjustment. She is standing tall and feeling great in that new bra (and the various other bras she went home with!). Shop this strapless bra for yourself below, and browse through the bonus styles she loved. 

Thank You & Boutique Support

Huge hurray and thank you to Drew Barrymore and her whole team. Not only for being brave enough to have this conversation about breasts and chests, but for being so open to my educational approach, and using a bra fitting as a coaching tool. 

I often have producers or female staffers come up after a segment to say thank you for the info, or that they never knew how cup size really works, or to ask me to give them a quick measurement. But I’ve never had the response like I did post show at Drew. These folks were ready to learn and thrilled for the information! 

I’m also sending a big thank you to The Rack Shack in Brooklyn for hosting us. Laura, the owner, and her staff were extremely accommodating, and let us play in their carefully curated bra drawers. I opted to bring these two gals there instead of a big department store for a few reasons: I wanted to support a small, woman owned, local business, and I know they have the size range and styles that I love because they’re also dedicated to fit. 

“Working with Kimmay, I felt safe. Kimmay has one of the most beautiful hearts. I just felt completely nurtured in this entire experience.” – Liza

Liza and Cassandra stayed well after our fitting to shop more bra styles and now have a brand new bra wardrobe. Stop by your local boutique and work with a pro to find your best fit and support. Hurray! 

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.

Your turn: What styles will you try? When is the last time you had a fitting? How did Drew and I inspire you to say hurray? Share with me @hurraykimmay on Instagram!

Credits:​ Big thanks to The Drew Barrymore show the producers and crew, and our lovely volunteers. I loved working with everyone!