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At 28 years old, I am a man— a guy?—who has never put any effort into being fashionable. That’s not to say I don’t care how I look. Nor am I one of those people who takes pride in being out of step with trends. It’s just that I don’t have enough energy or imagination to make deliberate, let alone sophisticated, decisions about my appearance, and I lack the perceptual machinery to understand what clothes mean—their connotations, what they say about me. If you asked me to construct an outfit that sent a message to strangers about who I am and what I’m like, I would stare at you blankly, like a cow at a fence.
And so I have come to Freemans Sporting Club, on Manhattan’s Lower East Side, to be converted. Not just made over, but convinced by the store’s team of haircutters and suit-fitters that I have been missing out—that, if I wanted to, I could be the kind of man I have always assumed I wasn’t.
As I wait my turn in the Freemans barbershop, I glance at the regulars—their hair already so correct that it’s unclear what they’re doing here—and wonder if it’s possible that, when I leave later today, I will be mistaken for one of them.
For the past year or so, I have been wearing the same thing pretty much every day: black jeans, a white V-neck, and one of the five identical button-downs I bought at Uniqlo in 2009. Before that, I wore clothes chosen for me by my mother. I have had the same haircut forever, except for a year when I had a rattail (I was 7) and that time in eighth grade when I grew bangs and shaped them into spikes using Elmer’s Glue. My favorite things to wear when I want to stand out are a stripy jersey, which my girlfriend calls my “heroin-addict shirt,” and a down vest that reminds me of Marty McFly’s cool red jacket from Back to the Future. At Freemans, I will be shorn, shaved, and dressed like a real modern man for the first time in my life.
Freemans Sporting Club is a lodestar for the rugged but pretty men of New York. It is a place that gives them permission to be finicky and purposeful about how they look—where they can work with professionals to craft an appearance without being made to feel unmanly. The barbershop at Freemans, known simply as “Barbershop,” was rebuilt only recently (from 300-year-old spruce reclaimed from an old barn) to accommodate the hundreds of customers who show up every week for haircuts, shaves, and beard trims.
I watch in the mirror as Ruben Aronov, the barber assigned to my case, stands behind me and talks with his associates about what needs to happen. “He has a good jaw,” one of them says. Then Ruben starts talking about what he’s going to do to the various “sections” of my head. I did not even know my head had sections. He takes the glasses off my face. The world goes blurry. I am acutely aware that I have just seen the old me for perhaps the last time.
While he works, I ask Ruben—who I find out later is part owner of the shop—what sorts of hairdos are requested by the typical Freemans man. (My usual line before someone cuts my hair is, “Clean it up, please, and leave the ears halfway covered.”) Ruben tells me that one time a guy asked him to shave his head but to leave a circular patch at the top. Another time, a fellow who was going to Burning Man wanted the hair on the back of his head arranged in an X. Those are outliers, though, Ruben says. A lot of guys come in asking for the “Ryan Gosling.” Others just ask him to do what he thinks is right. This is Ruben’s special power, I gather: He can look at a man and know how to shape his hair to capture his essence. When I came in, he says, he could tell I wasn’t going to go for anything extreme. “You’re not too conservative, but I don’t see you doing insanely edgy, youk now what I’m saying?” he says. “I don’t mean that in a bad way.”
I ask Ruben for some advice about keeping my hair looking good after I leave—and generally being a fashionable man once I’m out in the world. He recommends something called Mr. Natty Hair Clay—but he warns me that unless I really commit myself, it’s not likely I’ll stick to the program in the long run.(“If you’re not that guy, I dunno....”) Then again, he says, it’s possible the haircut will have such a profound effect that I’ll never go back to the way I was. “Sometimes I’ll change a dude’s persona so much that he’s like, ‘Whoa,’ you know what I mean?” Ruben says. “I swear, they’ve texted me at 2 a.m., drunk-texted, telling me, ‘Dude, I’m sorry it’s late, but I’m fuckin’ on fire right now!’ ”
This sounds like what I want! As Ruben shaves my face, using some Imperial Barber pre- shave oil, hot foam, and Aesop Shaving Serum, I fantasize about the circumstances under which I might feel compelled to text him tonight, with pretty girls passing me in the street and competing with one another for my eye contact. Before I know it, I am being handed my glasses. I take a breath, slip them on, and allow myself to come into focus. What I see astounds me: My hair is shorter on the sides than it has ever been, and long on top, where it is draped from right to left in a glossy, perky swoop. It makes me look focused, prosperous, and sure-footed. I look like a man who is supposed to be somewhere.
This, in fact, turns out to be true: I am late for my suit fitting. I thank Ruben and head next door, where a distinguished man named Jon Callahan and his associate, Winston Tolliver, have me try on something in “indigo” and something in what I’m told is Donegal tweed. Like all the clothes I’ll be wearing out of the store, they are designed in- house by Freemans Sporting Club.
“I’m doing whatever you say,” I tell them when they ask me what I think.
Jon likes the indigo—“The shoulder and the chest are perfect,” he says—but, after some debate, we end up going with the tweed, because the jacket is available in a smaller size, and it is explained to me that smaller, tighter, and narrower is a more modern look.
As I stand and look at myself in the mirror, I am amazed that this “traditional British tweed,” as it’s described to me—a material I have long associated with professorial lamewads—could look so cool. And while the pants are a little bunched up below the knee, I’m assured that a bit of tailoring will fix this and I will walk out with a “classic break” that leaves the bottom of the pant legs barely grazing my shoe tops.
Next up: the shirt and tie. “What’s your shirt size, do we know?” Jon asks.
We do not. “OK, let’s measure you.” After finding the best possible option—a dungaree shirt in a delicate robin’s-egg blue matched with a “tonal” tie that I’m told will look really cool—Jon submits, in the most diplomatic way possible, that I have kind of a weirdly shaped body. “You’re, in reality, a good candidate for having made-to-measure or bespoke, for both suits and shirts,” he says. “You’re tall. And you’re broad. And thin.”
Before long, I am face-to-face with a version of myself I have never seen. I look like I should be going to an awards show where I will win all the awards. Wearing my new clothes, I am led onward, through a bustling restaurant also owned by Freemans, toward a secret room for tailoring. I squeeze past beautiful young people eating brunch. Has my new look made me fit in with them? Or has it elevated me to some higher level? As such thoughts pass through my brain, I am worried that I will sweat through my shirt. Also, that I will get hives on my neck before my photo shoot, which happens to me sometimes. We enter the tailor’s quarters by way of a door camouflaged as a bookcase. There, I meet Alex Young, a wry man with a British accent, who is Freemans’ suiting director. He is wearing a brown suit with comically large pants, which seem to contradict some of the things I’ve learned so far today. “Your pants are very baggy,” I say, as he kneels down to measure my ankles. “Yeah,” he says, after getting back up to my level. “I like baggy pants.” Later, when we’re alone, he says he doesn’t consider himself a fashionable guy, and when I ask him if that makes his job at Freemans kind of difficult, he says he doesn’t think tailoring has anything to do with fashion. He tells me wearing trendy clothes is evidence of a “deep-rooted psychological issue,” which leaves me feeling confused.
As I walk onto the street and start toward home, I feel like a prince. When I glimpse my reflection in a tinted window, I stop to look.
On the subway, I think about the three parties I’ll be attending this evening with my girlfriend, Alice, and how, by the end of the night, I will have seen pretty much every single person I have ever met in New York City. I’m also thinking about whether I should buy the suit instead of giving it back the next day, like I’m supposed to. Although it costs $1,195, it seems like a bargain, given that I feel like a million bucks.
I walk in the door of the Brooklyn apartment I share with Alice, and right away I can see it on her face: She does not like my new look. “I hate it,” she says, not holding back.
“You hate it how?” I ask. I feel like I’m taking a cold shower.
She takes a softer tone. “Well, how do you feel in it?”
“I...I don’t know,” I say. Because all of a sudden, I don’t.