So when I started at GQ, I quickly learned that my closet was not up to the task. No one here dressed alike, but everyone dressed with purpose. The only intention behind my outfits was “Don’t be naked.” My boss gave it six months before I figured things out. It happens to everyone who comes to GQ, he said.
It has been three-plus years and I’m still waiting. That’s not to say I haven’t tried—a pair of A.P.C. jeans here, 18 pairs of Stan Smiths there. But I never quite turned “owning clothes” into “having style.” I wasn’t trying to go crazy with oversize Visvim ponchos or ugly-cool Balenciaga sneakers. I just wanted to give off David Beckham on a Weekend Coffee Run, but I couldn’t manage to get past Ben Affleck on a Vape Break.
And then I discovered Chelsea boots. I don’t remember where, only that once I saw them, I couldn’t stop seeing them—on red carpets, in magazines (like this one), on seemingly every other dude on the sidewalk. In a fashion universe where trends moved quickly and barriers to entry were high (“Baggy pants? With pleats?”), they seemed timeless, and democratic: Kanye looked great in Chelseas, but so too did all the hot dads in my neighborhood. I didn’t yet have the vocabulary to describe what I was looking at, but I knew they were sleek and sexy, not clunky like all the other boots I’d owned. (Plus they slipped on!)
Best of all? These boots—from New Republic—were only $99 and came in lots of different styles. I passed on brown leather (trying too hard) and camouflage (too teen hypebeast-y) and grabbed a pair in tan (“sand”) suede with a cushy crepe sole. They were elegant but non-threatening. I could imagine wearing them without a chorus of my longtime bros calling me Devil Wears Prada. Which makes sense: The man behind the boots—Mark McNairy, a veteran shoe designer—explained that this whole style thing doesn’t have to be so hard.
“You can put on a pair of Levi’s and a white T-shirt with a cool pair of shoes, and that’s all you need to make your statement,” he told me. And what did these particular boots say? “You’re timely. But you’re not an idiot who spends his money on unnecessary things.”
I was okay with putting that message into the world. But even though these boots weren’t that out-there, their stylishness quiet and personal, I was still nervous. So I wore them to dinner with a low-stakes audience to try something new on: my family. No one noticed, and I realized I could wear them without feeling like a complete poseur.
So I kept wearing them. I wore them with the few “fashiony” items I owned—those A.P.C. jeans; a dressed-down gray suit with a black T-shirt—hoping they would elevate my style. People at work started to notice. It was a small addition with an outsize consequence, like a spritz of cologne providing an extra layer of presence as I moved through the world. Walking to dinner one night, I felt like I’d finally slid into the slipstream, one more figure in the nightly parade of fashionable New Yorkers. Even at dinner, my boots hidden under the table, I got an added dose of confidence just from knowing they were there. Also: They feel like walking on memory-foam pillows.
And then one night, because it was raining and my boots were suede, I took a cab four blocks home. Had that moment of reckoning my old boss promised finally, belatedly, come to pass? Was I someone who cared about getting dressed?
Yes and no. I still don’t know much about fashion or What to Wear, but I don’t roll my eyes at the idea that caring about clothes might actually breed confidence. When I asked McNairy what he’d say to the guy—me—who was skeptical whether style really mattered, he drove it home: “You can not give a shit about clothes and still look super-fucking cool.”
But how? I’ll spend the next few months here, trying to figure that out—how you go about finding the denim jacket you want to own for life, or how to wear a necklace, or what a damn “grail” is. At the end, my style might not scream David Beckham Jr., but I’m hoping it’ll be somewhere beyond “grew up wearing athletic shorts in the snow.” Low bar, sure. But it’s a start.
Maybe foremost among the 7,648 reasons we love Chelsea boots? They’re perfect for your very first foray into fashion—but also for every last step on your own style journey. Whether you want harness hardware or cherry red designer soles, there’s a boot for you.
The Boot That Launched a Thousand Fits
Common Projects calf suede Chelsea boot
Chelsea boots now come in every color of the rainbow. But before you grab a pair in desert camo, try slightly out-there maroon.
$529, Neiman Marcus
A Bargain Bit
Aldo “Afille” Chelsea boot
One side effect of the Chelsea-boot explosion? You don’t have to fork over a grand for that coveted strap-and-ring piece.
Christian Louboutin “Samson” suede Chelsea boots
Buy for the details you can see, like that extra-sleek silhouette, and the one you can’t: CL’s famous red lacquer sole.