Mens Black Leather Jacket: What Actually Works

I have a spreadsheet. Not a metaphorical one, an actual Google Sheet called “Theo’s Closet” that I started three years ago and have never once let him see, because if…

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Jean Skirt: Everyday Looks

I counted them last Tuesday night, sitting on my bedroom floor with a glass of wine I probably didn’t need, and the number was eleven. Eleven jean skirts. Not eleven…

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Longline Coat: What to Wear Underneath

I’ve owned exactly three longline coats that actually earned their closet space, and I got there by ignoring almost everything the internet told me about wearing them. The reputation is…

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Brown Knee High Boots: From Casual to Dressed Up

The reputation on brown knee high boots is that they’re the safe choice. The boot you buy because you couldn’t decide, the fallback for when the black pair is at…

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Which Tie Goes With a Black Shirt?

I’ve been told, more than once, that a black shirt is a “put it with anything, it doesn’t matter” garment, the fashion equivalent of a blank wall. My brother in…

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What Color Pants Go With a Black Shirt?

I bought a pair of black pants specifically to wear with a black shirt for a job interview, and I want you to understand that I thought this was a…

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Black Chinos: Shirts, Shoes and Everyday Outfits

I was doing my Sunday inventory, the thing where I lay everything from Monday’s meetings across the bed and try to figure out if I actually need to do laundry…

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