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Chicago Manual of Style | Gentleman’s quarterly complaints

Always choose socks over flip-flops.

Photo: Tiffany Tan
The world of men’s fashion is strange and inhospitable. You think it’d be a progressive place, one which cultivates personal expression and artistic license. Clothing, after all, can be one of the most immediate indicators of our personalities. Even if you dress mindlessly, by virtue of being decent and clothed, you’re saying just as much about yourself as if you’d constructed your outfit meticulously. But men’s fashion, or at least its most lasting representation in popular America, certainly isn’t a welcoming space.

All of the ugly parts of sports culture—the stress on hyper-masculinity, the investment in the nebulous notion of “manliness,” which operates as the diametric opposite of anything “womanly”—are just as present in fashion. Seriously, though: GQ, which started as a men’s fashion magazine, is a prime example. Its “Men of the Year” special issue was printed with five different covers: four of the winning men in sharp suits, and a fifth featuring a naked and fetal Lana Del Rey. Magazines primarily targeted at women are constantly and justifiably lambasted because of the unrealistic expectations they set for women; it’s no different for guys. If I were to base “my style” off what the popular press tells me a man should be, I’d need an eight-pack, lethally sharp cheekbones, and those lower-back ass dimples. I’d need to maintain an expression of perpetually furrowed brows paired with a slightly open mouth, the male equivalent of duck face, as if to say, “I’m constipated, and feeling ambivalent about it.”

Yet there has been a new wave of expression in men’s fashion. Scroll through the tags on Tumblr and you’ll see sharply dressed men in incredibly fitted pants and checkered button-downs. Layers are also apparently a thing, and if I had more energy perhaps I would also match my undershirt to my button-down to my cardigan to my jacket to my coat, all of which I would then wear at once with some sort of magical array of folding so you could see different parts of each clothing article. I could try to rock a backwards hat, but I have a big head and most hats don’t fit on it, and anyway they suggest an aloofness I don’t think I can pull off. And that’s the thing about fashion, isn’t it?

As men are increasingly allowed to give a shit about their appearance, new implications begin to crop up. Maybe wearing a tie under a buttoned cardigan means you’re a little geeky, but in a charming Seth Cohen way. Maybe you’ll get a razor part and wear plaid shirts buttoned all the way up to your Adam’s apple to tell the world you’re edgy, but refined. Maybe you’ll rock a fringe or a fox fur, humming an overplayed rap song, as if the fact that you thrift is a badge of just how countercultural you are. “Grandpa style,” you’ll whisper to yourself, smiling because you’re just one kickass bolo tie away from living the life of a character from Skins.

I’m overthinking this. But when it comes to fashion, or I guess “men’s fashion,” my M.O. is simple: Give a shit. Aaron Sorkin wrote it best in his Social Network screenplay, as Andrew Garfield’s Eduardo Saverin screamed post-layoff: “Sorry! My Prada’s at the cleaners! Along with my hoodie and my ‘fuck you’ flip-flops, you pretentious douchebag!” Sometimes we just don’t feel like wasting brain power on clothing when it’s 9 a.m. and we’re already running late for Honors Analysis. Sometimes it’s easier to just wear the “fuck you” flip-flops and the Gap hoodie. And sometimes, that’s okay.

My manual of style: Mind your neckbeard. Sweaters are always, always a great option, especially in the winter. I’ve lived the last five months in a rotating collection of what are essentially blankets with sleeves. Just  make sure your seams line up with your shoulders, or slouch past them. Bigger is better in the winter clothing department; to go tight is to risk looking like a cased sausage.

I’ve been told we UChicagoans can get denim crazy, so perhaps if you’re wearing jeans and a jean shirt and then a jean jacket, you’re doing it wrong. I’m of the school of thought that believes the socks make the man. I have ’em warm and cozy and patterned with all sorts of things (both animate and inanimate). Wear them recklessly, crazily! Beckon strangers to corners, all whispery-like, and slowly lift your pant leg: you’ve matched your socks to your sweater. Watch as, wide-eyed, they stare into the face of a wool-knit god. Similarly, peacoats always look classy, double-breasted cardigans too, if you’re comfortable trying to pull one off. Avoid wearing all one color at the risk of looking like something made by RoseArt (not even Crayola, you monochromatic terror).

But above all, two pieces of advice: Be showered, and be confident. In the words of the great maker of denim, Levi, whose company was founded on the bedrock of appropriating the style of the working class, go forth! Just leave the “fuck you” flip-flops at home.

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