"Matt will probably be too cool for school to show up at reunion," reads the latest e-mail from our class officer, who never knew a pair of baggy chinos or penny loafers he wouldn't wear. "To see what he looks like now, just Google Image 'hipster.' Or you can reach him on Twitter, at #OccupyWallStreet."
I put my not-iPhone in my pocket — my contrast-striped, blue-and-green pocket — and get on the subway. Not downtown and home to Brooklyn, with my okay-they're-a-little-skinny gray jeans. Uptown, to the Collegiate School for boys — founded in 1628, the oldest school in America, JFK Jr., and all of that — with my plaid sport coat, my Ivy-inspired oxford, and my striped boat shoes. Not quite dress code — who wears a tie on a Friday night, much less to their tenth high-school anniversary? — but the stylish length of an Ivory Tower or five from Zuccotti Park.
"Well I think you win outfit of the night," says the reverend at the front door.
"I actually like that jacket," offers the former fat kid, with the Patrick Bateman hair and the private-wealth management pedigree. "I would wear that. Where'd you get that?"
I got it from the Esquire fashion closet, I tell him. From Michael Bastian's line for Gant. And, while I don't usually wear this kind of thing, I actually like it, too.
"I always thought it was Gahhnt," chimes in a voice from down the aisle. It's Teddy, god bless him, who always had his own personal style. When Collegiate made us wear blazers and ties with sneakers and jeans, he once walked down that aisle late to a Monday assembly, having just about made out with a Knicks City Dancer at a party the Saturday before, in a leather jacket and a skinny tie and he got a goddamn round of applause. "But you're a mean dresser."
"Mean" was never a word you used to describe the Collegiate boys back in the day — the kid with the Patrick Bateman hair, maybe, but not the nice smart boys who had to wear the uniform: a never-dry-cleaned navy blazer, maybe a polo shirt, or some novelty cartoon tie from the Warner Bros. store and chinos. Always the chinos. And they were still wearing the chinos at this reunion, all of my old friends from Park Avenue, whether they were on their way back to Park Avenue or to become some sort of rocket scientist on a yacht (really), and they looked at me — wearing extremely tight green pants, mind you — and asked where they could buy this sort of thing. Even Teddy looked kinda boring, and even the older guy who comes back every year made sure to get a picture with me and him and the rigid old dean, just so he could text it to the class: DRESS-CODE VIOLATION.
So a couple of whiskeys and a few days later, I asked Christoper Bastin, the head designer at Gant Rugger, what the hell was going on. "The whole preppy costume days are over, which I'm kind of happy about because it’s much more personalized today," he told me. "The stuff we're working on is a bit more grown-up, a bit more dressy — dressy but messy, not trying to look like your dad, but not trying to look like one of the guys from Dead Poets Society either."
You can't just buy a preppy look off some mannequin in Connecticut, is what he's saying. You have to violate the rules of where they came from.
It's true, though, that there is some sort of prep invasion going on in most stores these days. There was the kind of aggressive rugby thing a few years back, when I remember feeling a little bizarre going to a presentation for Michael Bastian's own line (not his Gant one I'm wearing) at a faux-locker room that involved a male model in nothing but a towel. And then, as Bastin says, "we and a couple other brands went along for the ride with the whole fancy heritage thing and came back." Back to trim silhouettes (I can feel that green jacket on my ribs, even after said couple of whiskeys) and to over-the-top details (Tommy Hilfiger has some seriously fantastic two-tone penny loafers right now) and to more colors of pants than the Google Image search for "hipster." You can wear these things without looking like a jackass — while looking like yourself — as long as you wear one thing (Chuck Taylors, maybe) that is definitively old and your own. Or, as Bastin suggests, just start buying everything a size smaller. "You don't want to be too comfortable," he says, "but just safe enough."
Myself, I still felt dangerously comfortable, even on this most uncomfortable of nights, dressed the preppiest at that preppiest of schools: I combined my girlfriend's reunion at the all-girls' school across town with ours, stayed up all night in that green jacket of not-mine, and wore the hell out of it to Esquire's Derby party the next afternoon. And to a Cinco de Mayo party after that. And to breakfast the next day. And I'm wearing it right now, actually. Although I guess I'd better return it.
Plaid sportcoat ($985) by Gant by Michael Bastian, us.gant.com; Oxford shirt ($115) by Style36o , style36o.blogspot.com ; chinos ($60) by TopMan, us.topman.com; boat shoes ($175) by Band of Outsiders for Sperry, sperrytopsider.com; belt ($40) by Style36o , style36o.blogspot.com
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