It started as a dare, if I’m being honest. My editor and I were having one of those late-afternoon conversations that happens when both of us are procrastinating on actual…
The precise moment I knew I had a problem was standing in the security line at O’Hare, watching a family of four check fewer bags than I had packed for…
The first time I ever walked into a thrift store with the intent to actually buy something, I was twenty-two and broke as hell. My first “real” job interview was…
I got a panicked text from my buddy Chris last Thursday night. “HELP. Got promoted to senior management. Meeting with CEO Monday. Entire wardrobe screams ‘junior analyst.’ No time to…
The first time I walked into a major tech campus in Palo Alto, I felt like I’d entered some bizarre social experiment where they’d eliminated all clothing choices to reduce…
Let me tell you about the weirdest day of my professional life. Last month, I found myself standing in the fluorescent-lit menswear section of a suburban Walmart at 7:30 AM…
I was sitting at a coffee shop in Williamsburg last weekend, watching the Saturday morning parade of guys in performance joggers, technical hoodies, and limited-edition sneakers, when it hit me:…
I have a navy cashmere sweater that cost me $320 back in 2011. At the time, it felt wildly extravagant—I’d just started at Style Authority, was making approximately nothing, and…
Three years ago, I stood outside a café in Florence during Pitti Uomo, watching a group of American buyers squint at passing Italians with the concentration of anthropologists discovering a…
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.…