802 Brittany Cobb: Founder & CEO of Flea Style

Feb 18, 2026

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On today’s episode, we welcome Brittany Cobb, Founder and CEO of Flea Style and author of the forthcoming book How to Style a Hat — a modern style guide and cultural manifesto centered on confidence, authenticity, and self-expression. What began as a small, underfunded side project rooted in Brittany’s love of flea markets and vintage culture has grown into a nationally recognized experiential retail brand valued at over $15 million, with seven locations redefining how people shop and connect with personal style.
Brittany’s path to building Flea Style was shaped by her early career as a lifestyle journalist and her instinct for storytelling — skills she seamlessly translated into entrepreneurship. Long before the shop-small movement gained momentum, she created a brand that celebrates individuality over trends and emotional connection over fast fashion. From launching The Original Hat Bar, an interactive concept that transformed hat shopping into a creative experience, to expanding into hospitality with in-store cafés and tearooms, Brittany has consistently pushed the boundaries of what modern retail can be. Her personal journey with melasma further deepened her belief in style as a confidence-building tool, inspiring both her brand ethos and her upcoming book.
In this episode, Brittany shares what it takes to build a category-defining brand from the ground up, why experiential retail is more relevant than ever, and how personal style can shape identity and self-expression. We talk about turning adversity into creative leadership, building emotional resonance in business, balancing the many roles of founder and mother, and scaling while staying authentic. A thoughtful conversation for founders, creatives, and anyone looking to lead with originality and confidence.

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To learn more about Brittany Cobb, Flea Style, & How To Style A Hat :
https://www.fleastyle.com/
https://www.amazon.com/How-Style-Hat-Decorate-Dream/dp/1419783564/
https://www.instagram.com/fleastyle/
https://www.instagram.com/brittanycobb/
https://www.linkedin.com/in/brittany-cobb/