The 10 Truly Unforgettable Fits We Couldn’t Stop Thinking About This Year

The Esquire Editors
·12 min read
Photo credit: Elaine Chung - Hearst Owned
Photo credit: Elaine Chung - Hearst Owned

From Esquire

When lockdown orders went into effect across the country earlier this past spring, the smash-hit series Celebrity Street Style: Another Picture of Someone Named Chris! seemed destined to go on temporary hiatus. The cottage industry that sprang up around documenting every famous guy-worn designer gem and yet-unreleased sneaker suddenly appeared doomed to become another casualty of a virus that continues to wreak havoc around the world. The once steady stream of eagle-eyed pap shots culled from the cultural capitals of the world slowed to a trickle—then stopped entirely as celebs hunkered down in their capacious Beverly Hills enclaves and did their part to flatten the curve (or at least pretended to).

In retrospect, we shouldn't have worried. Because faced with the grim reality of a global pandemic, the world's most beguiling dressers simply found new ways to get those fits off. Deprived of their usual outlets for creative expression, some took to the timeline to document their increasingly wild homebound looks, while others used every outdoor excursion, no matter how trivial, as an opportunity to flex—and flex hard.

The humble streets of cities across the globe took on a significance on par with the swankiest red carpet event. Otherwise mundane grocery store runs suddenly yielded photoshoot-worthy looks. Serendipitous trips to the corner store resulted in some of the best outfits of the year. And all of them provided a soothing balm for eyes made bleary from doomscrolling, offering a comforting simulacrum of normal life in otherwise abnormal times.

So in an ongoing effort to make sure the dedication of these unabashed Big Drippers didn't go unappreciated, we started keeping careful tabs on the whole lot of 'em. Now, as 2020 finally comes to a close, we're digging through the archives and taking a look back at 10 of the outfits that stuck with us—haunting our dreams, derailing our trains of thought—and breaking down why they still live rent free in our heads today.

In a year so replete with bad news it'll go down in the history books as one of the bleakest in recent memory, seeing any of these guys pop up unexpectedly while scrolling through the 'gram was enough to distract us for a brief, glorious moment, temporarily easing the collective headache we've all been nursing since March. Watching them give it their all—even if "their all" just involved a tattered old flannel and some slouchy jeans—made us want to get dressed again, if only to flick ourselves up and then promptly change back into the same pair of sweats we started the day in.

And because we're nothing if not generous, we rounded up a few of our favorite displays of pure sartorial strength so you can peep the fits we obsessed over this year and then snag some much-needed inspiration, too.

Peace out, 2020. We knew thee for way too long.

Justin Bieber's Dedication to '90s Skate Rat Style, 2/7/20

Photo credit: Pierre Suu - Getty Images
Photo credit: Pierre Suu - Getty Images

Over the last few years, Justin Bieber has gradually evolved into one of the most idiosyncratic dressers of our era. But in early 2020, the pop star's stylistic verve reached dizzying new heights, as he doubled down on the sleaze and embraced a look best described as "blissed-out late '90s ski instructor."

Drink it all in: the precariously perched beanie, the wraparound Oakley shades, the subtly pierced ears, the wispy mustache. (And that doesn't even include the sweatsuit in a fluorescent shade of highlighter pink, the throwback Lakers jacket covered in custom patches, and the chunky black skate shoes.) This was a big year for Bieber by any metric, but few accomplishments could top the sheer bigness of this fit.

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Harry Styles' Particularly Epic Run of Fits, 2/26/20

Photo credit: Kevin Mazur - Getty Images
Photo credit: Kevin Mazur - Getty Images

Choo choo! All aboard the Harry Styles appreciation train. First stop: hyperbolically hailing his every stylistic choice as a "significant moment in the way men are dressing right now." Sure, coverage of Harry and his styles (sorry) can get a little breathless, but this year the guy more than proved his mettle. Because here's the the thing about Harry Styles: He genuinely can't miss.

When the singer showed up to his performance on the Today show in February (wearing a pair of flared Gucci jeans and a patchwork cardigan from J.W. Anderson that would later launch thousands of TikTok-inspired imitations) he kicked off a tour de force display of pure stylistic mastery that lasted the whole damn year. In November, Styles made history as the first man to appear solo on the cover of Vogue—promptly breaking the internet in the process—but his run of outfits in the first stretch of 2020 is a tough milestone to top, even by his own high-flying standards.

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Bad Bunny's Statement-Making Skirt and Tee Combo, 2/28/20

Photo credit: NBC - Getty Images
Photo credit: NBC - Getty Images

Bad Bunny's never been shy about sending a message with the way he dresses, especially when it comes to upending age-old conventions surrounding the way a straight man should present. Performing on The Tonight Show in late February, the breakout star of the year rocked an oversized double-breasted blazer and a heavily pleated black skirt, dropping the former off his shoulders towards the end to reveal a simple graphic tee underneath. Bunny's tee read "Mataron a Alexa, no a un hombre con falda," or, in Engish: "They killed Alexa, not a man in a skirt," a reference to a trans woman shot dead in his native Puerto Rico earlier this year and the police report that misgendered her as a "man dressed in a black skirt."

Taken in context, Benito's outfit is a touching tribute to Alexa's memory and a poignant reminder that getting dressed is always an opportunity to make a serious statement—particularly when you're one of the biggest musicians in the world.

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Paul Mescal's Glorious Summer Glow Up, 5/27/2020

Photo credit: AM - Hearst Owned
Photo credit: AM - Hearst Owned

If you, too, finished Normal People this past spring and lamented the missed opportunity to see Paul Mescal in a fit truly worthy of his considerable talents (the man, it should be noted, looks like a fucking marble bust), lament no longer. Because this summer Connell was spotted swanning through the not-so-crowded streets of London and he—and his particular brand of "run me over with a truck" appeal—didn't disappoint.

If David Beckham is the personification of a certain type of buttoned-up British style, Mescal represents the opposite end of the spectrum, one inspired by elements of old-school football hooliganism—thoroughly scuffed sneakers, thigh-baring soccer shorts and all. Over the summer, Paul Mescal became the internet's favorite crush, and in a fit finally worthy of his leading-man energy, he and his sturdy, athletic gait could stroll into my life (and yours, tbh) and fuck it up completely any day he chooses.

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Offset's Kaleidoscopic Kapital Sweater, 6/18/20

Earlier this year, Offset posted a casual fit pic to the 'gram rocking an extremely wild sweater from the beloved cult label Kapital and a complementing pair of flared jeans in a shade of burnt orange reminiscent of homemade marmalade. (I'd like to imagine that the Migos, like so many of us, have a tacit understanding among their boys that when one of them pulls up in a fit this big, they don't even have to ask to be flicked up on the spot.)

Like any of his best bars, Offset's fit does a lot with a little. At the end of the day, he's just wearing a sweater and jeans. But taken in aggregate—including the Yankees hat and the AF1s (not to mention the neck truly flooded in I-don't-want-to-think-about-how-many-dollars'-worth of ice)—his outfit is one for the books. The sweater or the jeans alone would be more than enough to warrant mentioning, but the color-coordination on display here takes this fit to expert-level swerve territory. In a year chock full of expert-level swerves, it remains one of the best we've seen yet.

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Chris Pine in 'Oh Shit, Is That Dude Famous?' Casual, 8/6/2020

Photo credit: GPJR/Bauer-Griffin - Getty Images
Photo credit: GPJR/Bauer-Griffin - Getty Images

Smack in the middle of the dogs days of summer, Chris Pine threw down the gauntlet. Way back in August, The People's Chris stepped out looking like the poster boy for a whole lot of the shit we've been talking about here in an outfit that'll look as good this coming summer as it did then.

The mask is firmly affixed to the face, the shirt is trim and left open, the pants are slim and cuffed, the sandals are open-toed and well-worn. Topped off with a gold medallion necklace and a complementing watch in a similar tone (not to mention the big-ass hat), Pine's outfit is a perfect encapsulation of "oh shit, is that dude famous?" casual, pulled off by a master of the genre. He's not out here doing the absolute most (although, hell, he's no stranger to it). He's out here doing the absolute right amount. In 2020, that's more than enough.

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Cole Sprouse Elevating the Fit Pic to an Art Form, 8/25/20

This past summer wasn't the first time Cole Sprouse, former child star and current wispily mustachioed heartthrob, has flirted with the coveted menswear triple crown (sports!) that is getting off multiple big fits all at once. The man is no amateur. But the difference between your fit pics and his is that when Sprouse hits one of his boys to pull up ASAP and capture whatever heat he's rocking, he calls a photographer friend and stages a full-on impromptu photoshoot.

2020 is the year Sprouse did his damndest to elevate the friendly fit pic to an art form, doing it all wearing a version of what might aptly be described as Harry Styles lite—which, if you're literally anyone else, is a very heavy look. I mean, my god, man. This dude's hitting for the fucking cycle. (More sports!) In his tropical knitwear, slim-but-not-skinny denim, and Cuban-heeled boots, Sprouse didn't waste a moment of the precious opportunity, spotlighting a veritable cornucopia of current menswear touch-points with aplomb. Here's hoping he doesn't let up any time soon.

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Reese Laflare's Matching Jacket-and-Trouser Set, 9/8/20

On Instagram, where he dutifully documents his many, many fits, Reese Laflare is one of the swaggiest dudes around, making his account one very much worthy of a follow. Take, as a prime case study, this particularly spicy outfit from early September. You don't have to be a diehard clothing aficionado to appreciate the degree of mastery on display here, because his get-up speaks for itself; and boy does it speak volumes.

Lounging poolside in Tulum—huge mood!—Laflare effortlessly embodies Big Vacation Energy in some bonkers Loewe clout goggles and a standout jacket-and-trouser set from Needles, finished off with a pair of rainbow-embellished Gucci clogs (worn with coordinating pink Gucci socks, naturally) and a fistful of pearls slung artfully around his neck. He looks comfortable. He looks completely at ease. He looks exactly how we should all aspire to dress throughout this coming year—regardless of when we can actually take a vacation next.

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Brad Pitt's Low-Key Volunteering Look, 11/19/2

Photo credit: Coleman-Rayner - Hearst Owned
Photo credit: Coleman-Rayner - Hearst Owned

In November, Brad Pitt was snapped helping deliver groceries, yielding a veritable smorgasbord of grainy paparazzi shots more dazzling than any high-strung auteur's cinematic vision. And if there's another blessed image that more accurately captures the type of positive energy you should bring into the new year, I'm not sure I want to see it.

Shortly after Joe Biden was elected the 46th president of the United States, no one embodied the country's celebratory spirit more than Pitt (mask clinging gamely to one ear, hair delightfully unhinged, cigarette clamped firmly in mouth) trying to do some good after a long, arduous year while wrapped in a threadbare flannel and the only pair of clean pants left in the house.

In his distressed denim, scuffed slip-ons, and a fraying button-down vintage-hunters around the world would do unspeakable things to get their hands on, Pitt wasn't the hero we deserved, but he's definitely the one we needed. And if rocking a thrashed flannel and destroyed jeans while doing your best to restore some semblance of basic human decency to a world sorely lacking it—and enjoying a hard-earned cigarette every hour or so in the process—isn't enough to land you on this list, what is?

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Tyler, the Creator's Commitment to Getting Dressed, 12/11/20

Photo credit: GUMU, SPOT - Hearst Owned
Photo credit: GUMU, SPOT - Hearst Owned

We've been saying it for a minute now, but it's worth repeating: Tyler, the Creator is one of the best dressed dudes on the whole damn planet. If you follow the guy on IG, this probably isn't news to you. It doesn't matter what he's doing, Tyler's going to come correct. And that means he's going to come in some variation of this uniform, whether he's casually hanging out with Solange in a drool-worthy knit from Gucci or snagging groceries in an absolutely banging color-blocked cardigan, tobacco brown high-water trousers—cropped to reveal a healthy amount of sock—and neon yellow loafers. Tyler's an an aesthete through and through, and he's not dressing for anyone but himself.

It's that degree of commitment, more than anything else, that separates the Grammy-winning artist from the pack. Tyler, the Creator is out here making the most compelling argument I've seen yet for getting dressed not because you have anywhere in particular to go, but because getting dressed in and of itself is a pursuit worth indulging, and maybe even a vital one if you're starved for a fleeting sense of pre-pandemic dignity. So, in 2021, consider ditching the sweatpants and getting dressed like nobody but you is watching. In other words, make like Tyler—even if the only place you're headed is the grocery store down the street. Right now, that should be all the incentive you need.

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