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June 25, 2025 Shopping

The Truth About Custom Clothing: When It’s Worth It and When It’s Not

It started with a joke at a dinner party. My friend Dave—the kind of guy who’s perpetually fifteen minutes late because he’s changed outfits seven times—was complaining about decision fatigue.…

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June 23, 2025 Shopping

The ‘Investment Pieces’ That Actually Pay Off in Cost-Per-Wear

Last week, my mom called me in a panic. She was cleaning out my childhood closet in Chicago and found a shoebox with what she described as “an obscene amount…

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June 20, 2025 Shopping

The ‘Investment’ Menswear That Actually Holds or Increases Value

There’s a particular type of menswear salesperson I’ve encountered throughout my career—the one who, with practiced sincerity and unwavering eye contact, tells you that the $1,200 sport coat you’re considering…

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June 16, 2025 Shopping

The Gap/Old Navy/Banana Republic Items Actually Worth Buying

My apartment has a closet problem. Specifically, I don’t have enough closets to contain my borderline problematic shoe collection. At last count, I own 31 pairs—ranging from handmade Italian dress…

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June 13, 2025 Shopping

The Only 5 Shoes American Men Actually Need

My apartment has a closet problem. Specifically, I don’t have enough closets to contain my borderline problematic shoe collection. At last count, I own 31 pairs—ranging from handmade Italian dress…

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June 10, 2025 Shopping

The Fast Fashion Alternatives That Don’t Cost Much More

I killed a t-shirt last week. Not like, “oh this doesn’t fit right anymore” killed it. I mean I put it on, raised my arms to grab a coffee mug…

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June 9, 2025 Shopping

The Real Difference Between $50 and $500 Dress Shoes

I’ve got a pair of black cap-toe oxfords sitting on my desk as I write this. The left shoe cost $59.99 at a department store sale. The right shoe cost…

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June 2, 2025 Shopping

Baseball Caps Beyond the Ballpark: The Accessory That Defines American Style

I’ve got this Yankees cap that’s been through hell and back with me. Faded navy, brim perfectly curved (not bent, never creased—I’m not a monster), logo just weathered enough to…

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May 29, 2025 Shopping

The Athletic Brands Actually Worth the Premium Prices

I have a confession that would probably get my menswear card revoked if such a thing existed: my most expensive clothing purchase last year wasn’t a tailored suit or a…

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May 28, 2025 Shopping

American-Made Denim: Brands Still Manufacturing Jeans Domestically

The first pair of American-made jeans I ever owned were a complete accident. I was twenty-two, broke as hell, and had stumbled across a pair of raw selvedge Cone Mills…

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