HerMoney with Jean Chatzky: Bree McKeen on Reinventing a 100-Year-Old Industry, One Bra at a Time

Release Date: June 13, 2025

In this insightful episode of HerMoney, host Jean Chatzky sits down with Bree (Bri) McKean, the innovative founder of lingerie brand Evelyn and Bobby. Bree shares her journey of disrupting the traditionally male-dominated lingerie industry by designing a functional, comfortable, and supportive bra that addresses the unique needs of women today. Below is a detailed summary capturing the key discussions, insights, and conclusions from their conversation.

1. The Lingerie Industry Landscape

Timestamp: [02:37]

Jean Chatzky opens the discussion by highlighting the vastness of the lingerie market, valued at $13 billion, and its historical domination by male interests. She prompts Bree to shed light on why men have controlled this space for so long and how the dynamics are shifting.

Bri McKean:
“I call it the woman as cupcake metaphor, to be, to be decorated and consumed. For a long time, intimates were about how it made you look, how sexy it made you. It wasn’t focused on the engineering of the product.” ([02:58])

Bree emphasizes that the industry traditionally prioritized aesthetics over functionality. She notes that while feminist movements empowered women to own their sexuality, the engineering aspect of lingerie—critical for comfort and support—was neglected. This gap inspired her to create a bra that works with the body rather than against it.

2. Inspiration Behind Evelyn and Bobby

Timestamp: [07:58]

Jean inquires about Bree’s transition from a successful career in venture capital to founding her own lingerie company. Bree candidly shares her motivations, blending professional insights with personal discomfort.

Bri McKean:
“I was having a terrible experience wearing a bra. I had a big aha moment in my doctor’s office... my bra hurts when I stand up straight, you’re going to slouch.” ([07:58])

Bree recounts how persistent discomfort from traditional underwire bras led her to seek a better solution. Her collaboration with a physiologist revealed that the pain from underwires affected her posture, likening it to having a pebble in her shoe. This realization propelled her to design a bra that offers support without the associated pain.

3. Developing a Unique Bra Design

Timestamp: [05:08]

Jean observes the saturation of the bra market with numerous new brands and asks Bree what gap she identified that others missed.

Bri McKean:
“I created the world’s first completely 3D printed bra out of multiple materials. The EB core is a 3D sling that, together with the long line snug band, creates a shelf to support up to a K cup with no wire.” ([05:08])

Bree explains her focus on replacing the traditional underwire with innovative materials and design. Her approach involved extensive prototyping, including hundreds of 3D-printed models, to perfect a bra that serves large cup sizes without compromising on comfort or support.

4. Navigating Challenges in Product Development

Timestamp: [10:54]

Jean brings up Bree’s initial failure with a strapless bra prototype and its impact on her journey.

Bri McKean:
“The product was a lot heavier and bulkier than it needs to be. It had a proprietary fit algorithm that was too complex. I learned that simplicity is everything, especially for bras.” ([11:29])

Bree reflects on her first attempt to create a strapless bra, which did not meet consumer expectations due to its complexity and bulkiness. This failure taught her the importance of simplicity and user-friendly design, leading to the refined bras offered by Evelyn and Bobby that accommodate over 100 sizes and focus on ease of use.

5. The Importance of Patents and Intellectual Property

Timestamp: [14:24]

Jean delves into Bree’s experience with securing patents, a crucial aspect of protecting her innovative designs.

Bri McKean:
“The patent office found that there’s nothing like the EB sling. The underwire hasn’t seen much innovation since 1931, and my design offers a new way to support without the wire.” ([15:36])

Bree explains the difference between design patents and utility patents, emphasizing that her utility patents protect the functionality of her bras. She highlights the scarcity of innovations in the bra industry and how her patents provide a competitive edge by safeguarding her unique support technology.

6. Advice for Women Entrepreneurs Seeking Funding

Timestamp: [23:37]

Jean seeks Bree’s guidance for women looking to pitch their ideas and secure venture capital, particularly in a landscape where only about 2% of venture funding goes to female-founded companies.

Bri McKean:
“You don’t owe anyone any information about your company. Treat it like a two-way interview and go slow. Don’t let investors waste your time.” ([23:37])

Bree advises women to be strategic and selective when sharing information with investors. She emphasizes the importance of vetting investors to ensure they understand and value the problem being solved. Bree also shares her tactic of assigning homework to investors to engage them meaningfully, which ultimately led her to secure investment from a supportive male investor who could relate to the ergonomic challenges her bras address.

7. Brand Philosophy and Personal Inspirations

Timestamp: [28:28]

Jean asks about the origins of the brand name Evelyn and Bobby, highlighting Bree’s personal connections and inspirations.

Bri McKean:
“Evelyn represents beauty, inspired by my maternal grandmother who modeled lingerie in the 30s. Bobby represents purpose, inspired by my great aunt who taught me the importance of detail and entrepreneurship.” ([28:28])

Bree shares that the brand name honors the strong women in her family, symbolizing beauty and purpose. These personal stories underpin the brand’s commitment to creating high-quality, purpose-driven products that resonate with real women's experiences.

8. Closing Remarks and Future Directions

Timestamp: [30:39]

As the episode concludes, Bree offers listeners a glimpse into the future of Evelyn and Bobby, hinting at upcoming products like front hook bras and swimwear.

Bri McKean:
“I just tried on the prototypes and they're gorgeous.” ([30:28])

Jean expresses admiration for Bree’s dedication and looks forward to the brand’s expansion. Bree invites listeners to explore and purchase her products online or at various retail locations.

Conclusion

This episode of HerMoney offers a compelling look into Bree McKean’s mission to revolutionize the lingerie industry through innovation, intellectual property, and a deep understanding of women's needs. Bree’s journey from venture capital to founding Evelyn and Bobby serves as an inspiration for women entrepreneurs striving to make their mark in traditionally male-dominated fields. Her emphasis on comfort, support, and intelligent design underscores the importance of addressing real-life challenges with thoughtful solutions.

For more information about Bree and her company, visit evelynbobby.com or find Evelyn and Bobby products in Nordstrom, Von Maurer, and various boutiques across the U.S.