Styleforum, meet ChetB. He flits between CM and SW&D so easily you’d think he was an Internet ghost, but like many of us, he just has a lot of interests. This week, he tells about the lows and highs of online menswear hobby-chasing, and how he ended up where is today.

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Luxury Sweatpants (Or: What I Wore While Wasting My Life)

I saw the the best minds of my generation dressed by the internet, starving for 15% off codes, dragging themselves through the Mr. Porter sale section looking for an angry fix (preferably something blue from Japan).

Like other millennial dudes who grew up in the age of the internet, I too have suffered for #fashion. Questing for sick fadez, I sat in a bathtub with jeans on, the cold blue water swirling around me, as clouded as my judgment. I bought suede jackets from Belgian designers too expensive and delicate to wear in the kind of weather you need a jacket for. I wrote eBay listings with phrases like “pit to pit” and “plenty of life left.” I learned to tell forward pleats from reverse pleats and barely wince when I hear “shirting” or “trousers” or “pop of color.” I collected quote-unquote wardrobe essentials the way 80s kid–me collected baseball cards. At my lowest, I searched for cool walls to stand in front of while my wife took pictures of my outfits, which I then posted to the internet in order to farm thumbs from people named “Jet” and “Mr. Moo,” blurring my face to hide the shame.

I used the words “luxury” and “sweatpants” in the same sentence, in consecutive order. I sized down two. I sized up one. I wore shirts made from seven other shirts.

How did I get here? How did we get here?

Slip-Sliding the Slippery Slope

The answer, for me, is a question: “How should my suit fit?”

That’s what I asked Google a decade ago. I was starting my first job out of college and didn’t know how to dress for it. I landed on a site called Styleforum, a place where, among other banalities, grown men fight about how best to fold small pieces of silk. Years later, I’m still down the rabbit hole, exploring all the nooks and hidden passages, emerging only occasionally in chunky baller knits and/or drop crotch pants.

For as far as things have come, they started out slow. I spent a lot of time at first scouring dusty thrift shops, scooping up Paul Stuart ties, vintage Oxxford suits, and L.L. Bean boots. At that point clothing wasn’t so much a hobby to enjoy as it was a problem to solve. As if once you collected all the essential ingredients your closet was “complete.” Like beating a video game or something.

Things changed in a dingy thrift shop in rural Utah, when I happened upon a black Maison Margiela suit. It was like that scene in 2001: A Space Odyssey, when early man encounters the mysterious black monoliths. What’s with all the numbers on the tag? Why the exposed white stitches on the back, and the weird cut? Though I didn’t know what to make of it all, for $10, I took it home.

My tastes didn’t change overnight. But now I wondered: what else is out there? Soon my wardrobe of “sensible basics” started looking like a sea of boring, the blue Brooks Brothers collars rolling in like tiny waves. I was ready to start having more fun.

Dreeze Van What?

I never get the chance to talk about fashion IRL. (Except for once, at Costco, when a guy asked me if my Blue Blue Japan jacket was Engineered Garments, and if I knew where the taquitos were). Which is fine with me. I’d probably flub the pronunciation of my favorite designers’ names anyway.

But I’m happy that there’s a community online where it’s not weird to talk about how pants should “break” or why epaulets are lame. A place where people understand my excitement at finding a Hunstman of Savile Row shepherds check tie at Goodwill for a dollar (which, incidentally, I wore at my wedding a year ago) or a vintage shop coat or a Brioni jacket.

As time goes by, I find myself becoming less and less prescriptivist and narrow-focused and instead learning to enjoy all the vast possibilities. It feels sometimes like you’re supposed to pick a team: “I’m a Neapolitan tailoring guy,” or “I’m a workwear guy,” or “I’m a 90s sportswear guy” or “techwear is my thing.” But things are more interesting when you don’t pick a side.

Have fun. Experiment. Don’t be uptight about it. It’s just clothing.

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