The 10 Best Men's Fits of 2019
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By Lee Cutlip / December 31, 2019 12:55 pm

If there’s one thing 2019 blessed us with, it was men dressing well. The year might have been a strange, dizzying and often nightmarish one, but rarely did it fail to provide some noteworthy outfits.

Let’s first give credit where credit is due and thank the celebrities who shunned the monotony of the black tux in favor of something a little more unconventional. Men’s style is increasingly listing in the direction of — gasp! — personality, resulting in looks that reflect the wearer himself rather than the obvious hand of a stylist. This attitude also produced looks that increasingly challenged — and sometimes altogether disregarded — the rules of gendered dressing, a lesson that is well worth carrying into 2020 and beyond.

And so, from the vast amount of fits we saw this year, we’ve collected 10 of the best and biggest below. Treat it as a mood board for dressing bolder and better in the year that lies ahead.

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Shia LaBeouf


Shia LaBeouf has become something of a street-style god in recent years, amassing a cult following thanks to his normcore (or is it scumbro?) wardrobe. This year, the LaBeouf fit that caught our closest attention consisted of a cropped yellow sweatshirt, grey jeans, white socks and his beloved Nike Cortezes. Before you declare it un-extraordinary, consider the details: the sweatshirt’s worn inside out, revealing the fuzzy interior and seams; the pants expose a considerable amount of ankle; and the pristine white socks contrast with the battered sneakers. It’s “basic” yet elevated. But the real standout piece of this outfit is LaBeouf’s necklace, a hand-painted rendering of a clown in a tiny yet ornate frame that’s an homage to his dad. It’s odd, but that’s Shia.

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Timothée Chalamet


Little Timmy has been having yet another whirlwind year and shows no signs of slowing down. Thankfully for us, more films means more fits, like this magenta number he donned for the Little Women premiere in Paris. The suit, made by Stella McCartney, is yet another in Chalamet’s repertoire that challenges the notion of traditional suiting. Let it be known that Chalamet doesn’t have a stylist, meaning everything he wears is of his own volition and carefully crafted himself, and it shows. This might explain his decision to dangle an Eiffel Tower keychain pendant from his finger, thereby creating an entire new class of accessory.

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Frank Ocean


Any time the notoriously reclusive Frank Ocean deigns to make a public appearance, it’s a big deal. Because he reveals so little of himself, each outing serves as a fresh reminder for just how good his style is, and the range he possesses. The same person who wore see-through sequined Gucci pants for his 30th birthday can just as easily wear the more classic look you see above. It’s one that’s attainable even for us mere mortals, and will never fail to go out of style because it’s comprised of timeless staples: a navy blazer, white tee, subtly patterned pants and brown leather Wallabees.

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Robert Pattinson


Do not be fooled — this is not just a black suit and white button-up. Upon closer inspection you’ll find Robert Pattinson’s shirt is actually silk, with a black panel affixed to his blazer. It’s a hard fabric to pull off, and one that can easily veer into sleazy territory, yet Pattinson does it with ease. The suit, by Dior, vaguely resembles sleepwear without venturing too far into the casual. It’s the ideal getup for someone who wants to take a slight risk when it comes to formalwear without worrying about committing a fashion faux-pas.

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Young Thug


Drip or drown. This is the mantra by which the rapper Young Thug operates, and it consistently shows. Thugger has garnered a reputation in the rap industry for wearing clothes not normally attributed to rappers — ruffled blouses, tulle skirts, floral coats. In other words, he wears clothes that don’t adhere to a gender-binary way of dressing. Unsurprisingly, his sartorial choices have generated backlash and criticism within the hypermasculine rap community, but Young Thug does not care. While the outfit he wore for Gunna’s Drip or Drown 2 album release party is understated (yes, understated) for him, it’s nevertheless unconventional by normal hip-hop standards. The clashing patterns manage to work, and the cream turtleneck under the silk and velvet kimono-esque jacket lend him a sophisticated, professorial air, all while he holds a foam cup of Lean.

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Jonah Hill


If you were unaware, Jonah Hill has become a street-style icon of sorts. Now that he’s a serious actor and a serious director, his wardrobe must in turn reflect this, which for Hill often means dressing like a Lower East Side skater (which is essentially synonymous with fuccboi). But, that isn’t to say Hill’s style is bad; in fact, it’s quite good, as evidenced by the outfit above. For the Berlin Film Festival, Hill opted to go full European gallerist, meaning a purple coat layered over a checked sweater paired with slouchy track pants and day-glo orange Adidas. It’s sophisticated without being boring and shows that Hill is clearly in tune with contemporary trends.

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Bernie Sanders


Senator Sanders, is that you? The Vermont politician recycled his favorite Burton parka jacket (the same one he wore to Trump’s inauguration) and could easily have been mistaken for a Balenciaga model. What makes this fit particularly good is that Sanders is unaware of the effect; he’s wearing the jacket for utilitarian purposes and has no idea how much of a hypebeast he actually is, which makes it all the more endearing.

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Leon Bridges


This outfit largely flew under the radar, but it’s not to be ignored. The custom Bode suit singer Leon Bridges wore to the Grammys was born out of a collaboration between the Bridges and designer Emily Bode. Both have a penchant for the past, and the result of their work is a mustard-yellow corduroy two-piece that hearkens back to the ’40s and ’50s. The suit was decorated in drawings that paid homage to Bridges’s home state of Texas, including a cowgirl and the Ford logo. It’s a creation that looks like it was sourced straight from a vintage store, yet its specific and pointed reverence for the past and Americana makes it feel fresh and new.

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Tyler, the Creator


Tyler, the Creator is no stranger to experimenting with his wardrobe, and near the end of the year, he took a particular liking to dressing like a mid-century schoolboy. For the 2019 LACMA Art and Film Gala (sponsored by Gucci), for which many people arrive in their best black tie, Tyler went a different route and wore a mustard v-neck sweater over a striped blue button-up with a green tie, pleated khaki shorts (with a hat to match!), white calf socks and Dr. Martens mary-janes. It would appear the main style inspiration for Tyler is Prince George’s school uniform, and he looks like he would be right at home in a Wes Anderson film. Tyler has consistently dressed according to mood rather than trends, and it makes for an altogether more fun and interesting experience.

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Harry Styles


Harry Styles can do no wrong and everything he wears is a Fit with a capital F. Every kit Styles put together this year proved to be a contender for this list, but the ultimate winner was his BBC 1 Radio look. Although he’s donned flashier lewks, this outfit’s genius lies in its subtlety (subtle by Styles’s standards, that is): flared and high waisted trousers (a signature), a plaid Bode shirt/jacket, a tee from his own collaboration with Gucci’s Alessandro Michele, white Vans and a pearl necklace. Okay, so it sounds like a lot, but for Styles, it’s fairly tame. But let’s just pause and reiterate that he is wearing his own merch. While the jacket covers much of it, you can still clearly see “Harry Styles” (with Styles in strikethru) emblazoned on the front and enclosed in a heart. The world loves Harry Styles, and apparently so does he.