As Women's History Month draws to a close, it's worth noting that a bra design patented in 1931, featuring an underwire structure that encircled the base and sides of each breast, remained virtually unchanged for 88 years. This uncomfortable and unyielding design remained the dominant standard in the global bra market, a market projected to reach nearly $60 billion by 2032. McKeen, founder of Evelyn & Bobbie, left her job in Silicon Valley to address this personal problem.

Her experience at a venture capital firm provided valuable insights, but it was her own physical discomfort that prompted her to seek a solution. After long workdays, McKeen suffered from headaches and shoulder marks due to bra pressure.

Despite having no experience in fashion, McKeen, with a master's in medical anthropology and an MBA from Stanford, delved into research. A physiotherapist pointed out that her posture was excellent, but that the bra was causing her pain. This discovery led her to understand that the bra generated a neuromuscular response that affected her posture and well-being. “Here I am doing all this work to carry myself with authority and poise, and my bra, I find out, is totally doing the opposite,” McKeen said. “You don’t have to tell your body to curl around the pain. It just does.”

This realization marked a significant career change, abandoning venture capital to found Evelyn & Bobbie, one of the most disruptive women's brands. She moved to Portland, near Nike, Adidas, and Columbia, for inspiration and to establish new connections. She began experimenting with prototypes in her garage, immediately requesting intellectual property protection.

McKeen obtained her first utility patent (a harder, more defensible type that covers how something works, not just how it looks) within a year. The brand did not disclose the amount of funding it has raised, but now holds 16 international patents protecting its proprietary EB Core technology, which mimics the support and structure of a wire without causing discomfort. To put into perspective how critical it was to protect her intellectual property, only 12% of patents in the U.S. were awarded to women, according to the U.S. Patent and Trademark Office as of 2019. McKeen has six of them, protecting the unique 3D-sling technology in her bras.

The Evelyn & Bobbie brand, named after her maternal grandmother and her aunt, operates on the premise of a bra that fits well and feels comfortable all day. “I wanted a bra that made me look better in my clothes,” McKeen said, an inspiration reminiscent of how Spanx founder Sara Blakely started her shapewear empire, now valued at $1.2 billion. “Wire-free bras give you that mono boob—not a nice silhouette. They make your clothes look frumpy. I wanted nice lift, separation, a beautiful silhouette. I could not find that bra. How outrageous, really.”

The company differentiates itself through its approach to sizing, designing with 270 fit models in seven easy sizes, grading each style individually rather than scaling from a single sample. The average bra size in the U.S., McKeen pointed out, is 34F, a statistic that surprises most people, including the initial investors she once had to convince that comfort was a relevant selling point.

McKeen has achieved remarkable success, even having a Slack channel dedicated to customer love letters and a relationship with Dr. Nina Naidu, a New York-based plastic surgeon who sends the bras to all post-operative patients. With a luxury product comes a luxury price: Evelyn & Bobbie bras retail for $98 each. “Comfort is the new luxury,” she said. “We spend money on yoga pants that make us look and feel great. I’m going to make the premium bra the bra of the future.”