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June 25, 2025 52 mins

Why do men wear shirts under their shirts? Are you forever doomed to wear the same clothes as your 32-year-old self? Why isn’t male fashion more fun? Why are all these moms still buying clothes for their adult children? WHY IS EVERYTHING IN EARTH TONES? This week we welcome Jason Diamond to the show to answer all these questions — with side trips into slutty dad jorts, aspirational dad fashion, the joys of good tailoring, what it feels like when you put on something and really feel yourself, and just generally figuring out your style as an adult. This one’s very fun and very funny — a perfect summer listen.

Thanks to the sponsors of today’s episode!

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