Stylish

I’m Not Attractive or Successful. But Can I Still Look Stylish?

It all depends on how many chances you want to take — and how much you can spend on shoes

Based on the number of personal styling services selling clothes to men with ostensibly no fashion sense, it’s safe to assume that men don’t know how to dress themselves. Sure they know how to put on pants, and hopefully, they also know how to tie a tie. But ask the average guy to put together an ensemble, and most will wear clothes that will make him appear sloppy — at least so goes the marketing message of the aforementioned personal styling services.

But what does it even mean to be fashionable in the first place? Is calling someone fashionable just code for telling them they’re attractive and/or they have enough money to buy something that looks expensive? In other words, can someone “unattractive” ever look stylish?

The modern answer is, of course someone without typically attractive features can look cool. But it’s obviously much easier for someone who is conventionally attractive to wear whatever they want and make the clothes look couture. For example, Instagram influencer Luka Sabbat is considered a sort of avant-garde streetwear fashion icon. He’s often seen wearing oversized clothes, extra layers and even cargo pants — classic fashion faux pas. And yet, I dare you to try to find a single image of Sabbat where he doesn’t look like the personification of Gen-Z cool.

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“No cap”

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But it’s tough to imagine an Average Joe pulling off these “looks” as seamlessly as Sabbat. So then, if you’re not conventionally attractive, is there any hope for you to at least appear within the margin of error with regard to personal style?

Rayne Parvis, a personal stylist, certainly thinks so. “The key is confidence, charisma and/or swagger,” she says. “These traits are attained by having good posture, a confident voice and by dressing in a stylish manner that suits your personality. He should stand up straight, have a clean and well put together image and a voice that isn’t afraid to go after what he wants.”

But what does she mean on the last count — “clean and well put together” — which speaks directly to fashion sense?

“Washable, non-iron/wrinkle-free button-ups make great wardrobe investments and are easy to care for without the cost of dry cleaning,” she explains. “Second, having an up-to-date wardrobe with smart jackets (blazers, sport coats, bomber, racer and/or leather jackets) will elevate your look.” She adds that most people stop styling themselves at a top and a bottom, which is why she recommends a topper (jacket/sport coat/denim button-up) and an accessory like a watch to appear even more, ahem, put together.

Footwear matters, too. “No matter what type of shoe you choose, make sure they’re clean and cared for,” she says. “Ditch the dress shoes you’ve had since your first job interview that have scuffs and square toes.” Instead, she suggests simple style white street sneakers, chukka boots and other timeless dress shoes like brown lace-ups with a slightly pointed toe.

All of which is to say that you can look stylish if you’re not conventionally attractive. You might however have to lean toward wearing more classic, tried-and-true looks rather than a giant pink jacket embroidered with white crabs.