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June 2, 2025 British Style Fit & Tailoring Shopping Style Advice Wardrobe Basics

My Yankees Cap Has Seen More of the World Than Most People I Know

There’s this Yankees cap sitting on my dresser right now that honestly deserves its own passport. Thing’s been with me longer than most friendships, and I’m pretty sure it’s more…

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May 22, 2025 Fit & Tailoring Style Advice

Why I Wore the Same Outfit for 10 Years (And What It Taught Me About Dressing Your Age)

So I’m at Target last week looking for new undershirts – you know, the exciting life of a middle school teacher – when I catch my reflection in one of…

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May 21, 2025 Style Advice

Why Most Guys Are Overthinking Style (And the Three Things That Actually Matter)

So I’m standing in this cramped hotel room in Vermont watching my buddy’s brother completely transform someone’s entire vibe in like four minutes, and it hits me that most of…

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