Boots for walking. Probably a pair of vintage cowboy boots. They're from Red Wing, but this pair looks more like it walked out of an Our Legacy lookbook. They're all
black, made with a mix of smooth calf leather and bull hide that's got an intense grain, and a 2-inch heel. I feel hot when I wear them. That's what boots are supposed to do, right? After a lockdown spent working from bed, this pair of hard-soled boots motivated me to go outside to see people again (and to be seen by people). It's also been great for my legs because cowboy boots apparently exercise completely different leg muscles than the spongy sneakers I'm used to. — Gerald Ortiz
Art. Each purchase I made this year was more considered than the last. (In my head, I dubbed it The Year of Magical Copping.) I found myself drifting away from purchasing clothes and more focused on things for my home. I bought a painting from artist Joe Henry Baker—a watercolor on raw canvas with a simple wood frame well over four feet wide. It is the most significant piece of art I've ever purchased. And now it's hung in a place where it is one of the first things I see when I wake up in the morning. The painting makes me happier than any pair of pants or sneakers I've ever owned—I just wish it didn't take a damn pandemic to make me realize I should be buying more art. — Tyler Watamanuk
Spikes. Like many American bozos, I spent most of my non-couch leisure time in the one place where I reasonably and safely could: on the golf course. One nice thing about golf is that the game simultaneously stokes a bottomless desire for new gear while reminding you, with every chunk and skull and slice, that all that fancy new stuff won't help you, anyway. (That didn't stop me, of course, from loading up: on clubs, on polos, on balls and ball markers and divot tools and training implements and a net to hit into in the backyard.) But even a bad golfer needs golf shoes, so as not to fall down while shanking yet another tee shot. So the best thing I bought this year was a pair of black golf spikes, their black leather saddle-shoe construction hiding a futuristic chassis underfoot. They do not look cool. But they keep my feet glued to the ground, and for that, I am thankful. — Sam Schube
No sleeves. It all started on a rainy day in June, pacing through the West Village, when I stumbled upon a small vintage store I’d never seen before. After stroking through racks of old suits and sweaters, a talkative woman dressed in all Ralph Lauren greeted me. “You need this,” she said behind two cloth masks. Simultaneously, she reached out her arms and held up a dark purple Ralph Lauren cashmere sweater vest. I’ve never thought of myself as the type of person who sports eggplant, but I've worn it often since. — Willa Bennett
My own handiwork. How about the best piece of clothing I made this year? Back in September, I dipped my toe in the ever-booming bootleg merch waters by printing up a couple dozen shirts with the immortal Rob Reiner emblazoned on the front, and his untouchable '80s and '90s directorial run (Stand By Me! When Harry Met Sally!! A Few Good Men!!!) listed on the back. Receiving orders from actual people for a dumb thing that I designed is far and away the greatest drug I've ever tried, and rest assured I'll be chasing the dragon with new tees in 2021. — Yang-Yi Goh