114. Finance and Fashion

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Does what you wear to work on Wall Street matter? How much? Why? What exactly are you supposed to wear, anyway? 

Who makes those decisions? And how can you express your personal style in a way that elevates your career?

In this inspiring conversation with former finance PR specialist-turned-fashion-founder Kerry O'Brien, the CEO of Commando, we learn how to navigate all of these questions in a fun, freeing way.

Kerry gives us insight into her innovative, technology-forward approach to fashion, her personal philosophy about taking risk, and her solutions for some of the classic problems we run into when it comes to fashion in finance.



Kerry O’Brien is the visionary founder, CEO, and designer behind Commando, a brand renowned for its unique blend of technical innovation and elevated design. After a successful career in financial public relations in New York City, Kerry set out to redefine the way women experience intimate apparel, transforming her passion for problem-solving into a game-changing endeavor.

With no formal background in design, Kerry launched Commando in 2005, introducing the industry’s first ever raw-cut, elastic-free, invisible undergarments. What began as a mission to deliver exceptional comfort and confidence has evolved into a brand synonymous with innovation, with Kerry holding two patents for her groundbreaking work in hosiery and slips.  In 2012, Kerry was inducted into the Council of Fashion Designers of America (CFDA), solidifying her status as a pioneer in the industry.  Today, Commando’s designs are seen on red carpets, runways, and magazine covers worldwide, making it a trusted favorite among stylists and celebrities alike. 

Under Kerry’s leadership, Commando has grown from its pioneering signature raw-cut intimates to a full ready-to-wear collection that continues to push boundaries in technical fabrics and modern aesthetics. Kerry has applied commando’s raw-cut and comfort-obsessed philosophy to many corners of your closet by designing long lasting, timeless wardrobe essentials that you can wear on repeat season after season. This commitment to excellence and ingenuity earned her a Femmy in 2024 for Brand Evolution, the intimate industry’s highest award. 

A sixth-generation Vermonter, Kerry lives in Burlington with her husband and three children. Her products are available in over 500 premium retailers, including Bergdorf Goodman, Bloomingdale’s, Neiman Marcus, Net-a-Porter, Nordstrom, Saks Fifth Avenue, and at https://www.wearcommando.com.

Links to shop items discussed on the podcast:
https://www.wearcommando.com/collections/ceo-collection-chic-easy-outfits

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