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How To! with Charles Duhigg

How To! with Charles Duhigg

How to Feel Good in Your Clothes

Jul 21, 2026 · 34m

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On this episode

About this episode

Today on How To!, Michael, a retired FDNY captain who used to rely on a uniform every day, finds himself staring blankly into his closet and canceling dates because he does not know how to dress. Host Mike Pesca brings on Tavia Sharp, an executive image and personal brand strategist and founder of Styled Sharp, to help Michael navigate post-retirement style, move past 1990s baggy clothing trends, and overcome the challenge of finding proper-fitting clothes as a shorter guy. They discuss the concept of building a practical "capsule wardrobe," why you shouldn't blindly trust store clerks who call themselves stylists, and how to shop for your specific body type. Plus, is adopting a color…