Courting The Next Era Of Tennis Style with Courtney Kelly

Today, I have the pleasure of sitting down with Courtney Kelly, founder of Courting - a tennis-inspired brand rooted in nostalgia, community, and seriously good style. What started as an idea for a tennis themed coffee shop (and even a matchmaking app) evolved into a full collection that blends performance, functionality, and fashion in the coolest way. We talk about the real story behind Courting - from growing up around tennis in the 90s to reimagining what the sport looks and feels like today. Courtney shares what it actually takes to build a brand from the ground up: trademarking your idea, pushing through endless design iterations, and learning when to trust your instincts. We also get into starting something new later in your career, navigating stability vs. risk, and letting go of the idea that there's a "right" timeline for success. Plus, a behind the scenes look at what it's been like working together on the collection, and why tension, honestly, and creative trust are the magic ingredients. Courting is about more than just tennis fashion, it's about community, self-expression, and doing something because you genuinely love it. This episode is brought to you by Alice + Olivia, Sam Edelman, and Jones Road Beauty. Exclusively for With Whit listeners, you can get 15% off everything from new arrivals to best sellers by visiting aliceandolivia.com/whit Visit Samedelman.com to explore everything you need for spring and get 15% off with code WITHWHIT15. For a limited time our listeners are getting a free Jones Road Beauty Shimmer Face Oil on their first purchase, just head to jonesroadbeauty.com and use code WITHWHIT at checkout. This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode. Produced by Dear Media See Privacy Policy at and California Privacy Notice at .

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Courting The Next Era Of Tennis Style with Courtney Kelly is an episode from With Whit by Dear Media.

This episode is 00:55:02 long.

This episode was published on Mar 24, 2026.

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