Oh, the stories a bra fitter could tell… and I’m doing just that in this solo episode of The Hurray Show. After 20+ years in fitting rooms with thousands of folks, I’ve learned that what’s happening under the bra is just as important as what’s happening under the surface. In this intimate conversation, I’m opening up The Fitter Files—a storytelling series that blends practical fit advice with powerful lessons on worthiness, support, and self-love. Whether you’ve delayed shopping for a bra, avoided your reflection, or waited to feel “ready” to honor your body, this episode is here to lovingly challenge those old beliefs. Let’s rewrite the story of support, starting today.

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

Show Notes

Oh the things you’ll learn after 20+ years of fitting folks for bras. In this solo episode, host Kimmay Caldwell dishes on the truth behind the curtain, and shares powerful, personal lessons from The Fitter Files, a storytelling series based on her 20+ years as a bra fitter. What if the support you’ve been waiting for…is something you actually deserve right now? 

Through emotional insights and practical wisdom, Kimmay challenges the toxic belief that worthiness must be earned or delayed until your body changes or you think you’re “enough”. This episode is more than just about bras. It’s an opportunity to step into support (in every sense of the word) NOW. 

From financial fears to shame-based shopping, and fitting room tears to joyful breakthroughs, Kimmay invites you into a conversation about radical self-care, rejecting tempting societal norms, and honoring your body exactly as it is today. Hurray!

Key Takeaways:

• An introduction to The Fitter Files: How sacred support led to life lessons; Kimmay’s new series of the powerful takeaways after 20+ years of fitting folks for bras
• You Deserve Support Now: Kimmay will explain how delaying your bra support has massive implications beyond the bra, and what you can do about it 
• Understand the Ripple Effect: Learn how if you do something in one area of your life, you’re likely to do it in another (and how to take a step toward your hurray!) 
• The “F Words” Holding You Back: The 6 “F Words” that are stopping you from supporting your body and stepping into your worthiness today 
• Start Now, Not Someday: Simple and powerful truths to shift your perspective and finally take a small (but important) step toward honoring the body you have today – not in 10 pounds, 10 years, or once you have a partner

Mentioned in This Episode:

The Fitting Room Files – An introduction to a powerful new series on the show uncovering emotional truths and self-worth lessons straight from the fitting room.

Bra Budgeting Article – A thoughtful guide on how financial investment in bras is also an investment in self-esteem: 

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

“Your body is not a problem to fix. It is worthy of care, support, and celebration right now.” – Kimmay Caldwell

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!

Your Turn: What’s one area of your life where you’ve been waiting to feel “worthy enough” to begin? Have you ever delayed buying a bra or offering yourself support because of finances, fear, or shame? 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.