Best Shoe Colors for a Light Gray Suit

I own four light gray suits and exactly eleven pairs of dress shoes that could theoretically go with them, and I counted last week because a friend asked me what…

Read more

Slim Fit Jeans: Shoes That Suit

I bought a pair of pointy white leather sneakers off a resale app at eleven fifteen on a Tuesday night, absolutely convinced they were the missing piece to every pair…

Read more

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…

Read more

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,…

Read more

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…

Read more

Velvet Blazer Styling: Black and Colored Options

My roommate walked into the kitchen, looked at me for a full three seconds, and said, “okay, who died.” I was wearing a black velvet blazer over jeans and a…

Read more

Blue Suit Shoes: What to Wear on Your Feet

Okay so I counted last week because I was packing for a wedding and had to physically go through my shoe rack, and the number of pairs I own specifically…

Read more

Blue Shirt: Tie and Pants Pairings

I counted it up the other week out of pure boredom: seventeen. That’s how many times this year I’ve been asked, mid text message or mid panic in my own…

Read more

Womens Blazer: What to Wear With It and Underneath

I counted my blazers this morning, actually got up and counted, because a client asked me last week how many I owned and I genuinely didn’t know. Eleven. Eleven blazers…

Read more

Black Denim Jacket: Jeans, Pants and Shirts That Work

My sister called me on a Tuesday, which she never does, just to tell me she’d seen a photo of me in my black denim jacket standing next to my…

Read more