When was the last time someone actually taught you how to shop for a bra? For most of us, it’s been a mix of trial-and-error, awkward fitting room moments, and maybe a tip or two from a well-meaning friend. In this solo episode of The Hurray Show, I’m your cool teacher for Bra Shopping 101 — whether you’re heading back to school or just back to the basics. I’m pulling back the curtain on everything I’ve learned in 20+ years of bra fitting so you can skip the confusion and go straight to feeling supported, comfortable, and confident.

Listen now on your preferred platform: Spotify, Apple Podcasts, Amazon Music, or YouTube.

Show Notes

Class is in session! In this solo episode of The Hurray Show, host Kimmay Caldwell transforms into your favorite cool teacher to guide you through Bra Shopping 101 – no matter your age or stage of life.

Whether your last “lesson” on bras came from a parent, a magazine, or social media, it’s time to toss out the outdated info and learn the real deal. Kimmay walks you through the basics of size, fit, sister sizing, bra wardrobes, and care – plus, why it all matters. If you’ve been wearing bras over your most sacred vessel (your heart) without ever being taught how to find the right one, this episode is for you.

It’s everything you were never taught about bras but should have been! Pull out your pink notebooks (or just hit play) and get ready to graduate from confusion to confidence.

Key Takeaways:

• Know Your Size, But Don’t Be Defined By It: Your bra size is a starting point, not a final destination. Kimmay breaks down how and why your size might change and why the number on the tag isn’t the final say.
• Fit is Everything: Forget the straps, it’s the band that’s doing the work. Learn why fit is the #1 factor in support and how to get it right.
• Understand Sister Sizing – Bra Math 101: Time for a little “bra math.” Learn how cup volume shifts with band size, and how sister sizing can help you adjust to find a comfortable fit.
• Build a Bra Wardrobe: Kimmay outlines the five types of bras nearly everyone needs to round out your bra-drobe for any occasion.
• Care Matters: How you wear, store, and wash your bras can extend their life and support. Learn the best practices that earn an A+ in bra care.

And above all: Your worth cannot be measured by a number. You are worthy of support, comfort, and confidence right now.

Mentioned in This Episode:

Free Fit Guide – Kimmay’s compassionate tool to help you find a bra that fits your body, not a number or expectation

Supportive Sports Bra Guide – Kimmay shares her expert picks and explains how to choose a sports bra that actually supports your movement and your body (without squishing or sacrificing comfort)

How to Care for Your Bras – This guide includes simple, practical tips on how to store, wash, and wear your bras the right way

Other Valuable Resources:

• Why 9 Bra Sizes All Fit
• Buying & Storing Your Best Bra Wardrobe
• How “Sister Sizing” Works
• Bra Confidence and Comfort Course

All that and more on this episode of The Hurray Show. Listen now and start celebrating your own story, one HURRAY at a time.

Don’t forget to like, comment, and subscribe for more inspiring stories!

Connect with Kimmay Caldwell:

• Share your thoughts and connect with Kimmay on Instagram – https://www.instagram.com/hurraykimmay/ 
• Get special show info, links, and more at https://www.hurraykimmay.com/podcast 
• For more valuable content, subscribe to The Hurray Show on your favorite platform: YouTube, iTunes, Spotify, or Amazon Music 
• Leave us a review on all popular podcast platforms and share how this episode has impacted you.

More visual? Hop over to our YouTube channel and hit the subscribe button to watch the show: https://www.youtube.com/@hurraykimmay 

Your Turn: What’s one thing you wish you’d learned about bras years ago? Which type of bra in your current wardrobe do you reach for the most, and why? Share your thoughts with me on Instagram or TikTok!

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.