Mens Black Jeans: Building Outfits From Tees to Jackets
I ironed my black jeans once. Properly ironed them, crease down the front like school trousers, because I had a second interview for a job I badly wanted and I’d…
Sweater Dress Styling: Shoes, Boots, Coats and Jackets
My roommate walked into the kitchen on a Tuesday, looked at me for exactly two seconds, and said, “You’re wearing the vacuum sweater as a dress again, aren’t you.” Which,…
Wide Leg Joggers: Tops, Jackets and Shoes That Keep Them Polished
I was folding laundry on a Sunday afternoon, the kind where the pile has gotten embarrassing and you promise yourself you will never let it get that tall again, when…
Best Shirt Colors for a Gray Suit
I own a charcoal gray suit that I bought for my cousin’s wedding eight years ago, and for the first two years I wore it exactly once, to that wedding,…
Gray Suit Shirt Patterns and Colors
I own six gray suits. Not by design, not some capsule wardrobe manifesto, just the slow accumulation of a decade where gray kept winning over navy at the tailor’s counter.…
Brown Sneakers: Outfits and Socks
Brown sneakers have a reputation for being the shoe you buy when you’ve given up. The safe choice. The “I don’t want to think about this anymore” purchase that sits…
Best Shirt Colors for a Light Gray Suit
I own eleven dress shirts that exist for exactly one reason. A light gray suit I bought three years ago from a shop in Wicker Park that has since closed,…
Denim Jacket for Guys: Outfit Ideas
I own seven denim jackets. Seven. I counted them Sunday night while doing laundry, laid them out on the bed like some kind of evidence board, and just stood there…
Sneakers: Socks and Outfit Ideas
Seventeen. That’s the count, and I did it twice because I didn’t believe myself the first time. Seventeen pairs of sneakers lined up along my hallway in Chicago, in an…
Best Shirt Colors for Brown Pants
My sister in law walked into Thanksgiving last year, looked at my brown corduroys and my white button up, and said, “Oh, you look like a substitute teacher who’s about…