Timothee Chalamet, Jeremy O'Harris, Justin Bieber, Harry Styles
Neil Mockford/Jacopo Raule/MEGA/Karwai Tang

The 10 Biggest Menswear Fits of 2020

The best fits of this crazy year reflected the chaos without succumbing to it

In a year largely confined to the indoors, outfits were left relegated to the imagination, something to be conceived in one’s mind with the hope of being fully realized in the distant future. While our wardrobes were increasingly infiltrated with sweatpants and tracksuits, we could (and continue to) hold ourselves over with our imagined outfits until the time to start really dressing presents itself again.

But for some, not getting dressed was never an option. Despite the prevalence of athleisure, these individuals refrained from giving in to the cozy and comfy narrative that dominated fashion and retail, persevering in the face of a pandemic to deliver outfits worthy of being seen. Or, they did what any true fit connoisseur would do and they adapted, adjusting their style in accordance with the current climate without sacrificing it altogether.

Granted, for celebrities having to contend with the omnipresent paparazzi or attending award shows and press events, even in the midst of a global pandemic, there remains little choice when it comes to being seen or not. But despite the constant exposure, there was an evident change in the famous and their own manner of dressing, which either saw them acclimating to the times with more casual clothing or taking risks they may have avoided pre-pandemic.

So in a year that seemingly should have been devoid of big fits, there was a wealth of them, many which sought to and successfully challenged the gender-binary way of dressing or re-define what casual wear is. Below are 10 of the best fits that spoke to the strange year 2020 proved to be or those that seemed to represent a new, less traditional direction in menswear.

Harry Styles
Karwai Tang / Jim Dyson

Harry Styles

If nothing else, 2020 blessed us with a few red carpet looks from Harry Styles, one of which is the above from the BRIT Awards. Slightly pared back in comparison to some of Styles’ flashier looks, the outfit succinctly captures the musician’s approach to fashion: masculine tailoring with feminine details. The strong shoulders and wide lapel of the suit could easily have been made more macho with the addition of a standard button-down underneath, Styles instead seeks to turn the traditional suiting on its head by pairing it with a scalloped collar and pearl necklace. The purple sweater acts as neutral territory between the two opposing aesthetics, allowing them to come together in a coherent manner that juxtaposes masculinity and femininity, presenting them as ideas that can (and should) coexist.

Timothee Chalamet
Neil Mockford/GC Images

Timothée Chalamet

A huge departure from his brazen red carpet looks, Timothée Chalamet exhibits a much more understated and inconspicuous manner of dressing in his day-to-day life (most likely in an attempt to go unnoticed in the event he runs into a horde of teenage girls). While his everyday style might be simple, that isn’t to say it’s unexceptional. Just as with his black-tie and red carpet looks (which he styles himself) Chalamet exhibits a careful and conscious hand when it comes to selecting pieces, showing that he’s attuned to trends without strictly adhering to them. His outfit for a stroll in Notting Hill is a dalliance with normcore, thanks largely to the New Balance 990v5s and muted tones, yet details like the Prada logo on the nylon jacket or the aggressive center crease along the pants rescue it from complete anonymity.

Adam Scott

An outfit more attainable for the rest of us, Adam Scott managed to achieve the ideal work-from-home fit during the first month of quarantine. At first glance Scott’s look might read as unremarkable, but when placed in the context of the year, it presents itself as the perfect casual yet not too casual fit. The slightly loose gray sweater thrown over the yellow tee indicates an air of carelessness while the artfully rolled jeans, slouched retro-tube socks and beat-up sneakers still exhibit a sense of style and pride in one’s outward appearance. It’s a look conducive to both the indoors or a quick jaunt outside, one that says, “Why yes, I just haphazardly threw this on and still look amazing.” And we’d be remiss not to mention Scott’s headwear of choice — a visor with tufts of hair sticking crazily out the top.

Paul Mescal
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Paul Mescal

When photos of Normal People star Paul Mescal wearing some near-micro shorts surfaced some time in May, it was all anyone could talk about, and understandably so. The Irish actor showcased an impressive expanse of thigh in a pair of athletic shorts, paired with a colorful Adidas jacket, slightly scuffed Stan Smiths and Clubmasters. The other elements of the outfit fall by the wayside as it’s hard to notice anything but the shorts, yet it’s not merely the length that is admirable, but the confidence and even offhand manner in which Mescal wears them, as though he might as well be wearing a pair of jeans.

Jeremy O'Harris
Jacopo Raule

Jeremy O. Harris

Before Harry Styles donned a tulle dress on the cover of Vogue, playwright Jeremy O. Harris arrived to the Venice Film Festival in a pleated Thom Browne skirt, dolphin-print blazer and Gucci Horsebit Orgasmique tote. Harris has never been one to follow a binary way of dressing, so it’s only natural he would be attracted to Browne’s similar design ethos, one which frequently results in skirts in menswear collections. It’s an outfit consisting of recognizable and highly-coveted pieces that reads as authentic because of Harris’ ingenious styling and his frequent wearing of these designs in his everyday life, so there’s nothing gimmicky happening here.

Justin Bieber
CrownMedia/Mega/GC Images

Justin Bieber

The Justin Bieber of recent years has been prone to sporting Drew House, his own line of loungewear-adjacent clothing, but this June he exhibited a slightly more mature and polished look while filming a music video. The outfit still feels appropriate for Bieber, falling somewhere in the realm of LA skater bro, but a little less douchey. The textured button-up over the white tank and Dickies-esque pants remain achievable enough, but what’s most impressive is Bieber’s ability to effortlessly pull off Dior’s Air Jordan 1 OG sneakers. For those lucky enough to have acquired the sneakers (or hoping to) take note in the casual way Bieber wears them, as though they’re just another pair of sneakers, yet keeping the rest of the outfit relatively simple so they’re still noticeable.

Brad Pitt
Jeff Rayner/Coleman-Rayner

Brad Pitt

Would this look have the same impact if it were worn by anyone else besides Brad Pitt? That’s debatable, but the fact of the matter is he’s wearing it and he looks damn good. Pitt makes the case for the classic white t-shirt and blue jeans combo, keeping both slouchy, throwing a plaid shirt on top complete with a rip on the right side of the chest. Paired with his tousled locks and ability to look cool while smoking a cigarette, this may very well be an instance of the man making the outfit. But again — who cares? He looks hot.

Tyler, the Creator
Jon Kopaloff / Steve Granitz

Tyler, the Creator

The genius of Tyler, the Creator’s 2020 Grammy outfit lies largely in the concept, the rapper arriving to the awards show in a Wes Anderson appropriate bellhop outfit with suitcase in tow. Post-ceremony, Tyler changes into a red and pink striped collared shirt, brown slacks and baby pink desert boots, the same outfit that Tyler had been toting around in his pink luggage pre-ceremony. Outfit changes are commonplace at award shows, but none have been as inventive as Tyler’s, a slightly discreet and campy way of making the change that felt more for himself and his own enjoyment than it did for the audience.

Luca Guadagnino
Carlos Alvarez / Frank Lovicario/NurPhoto

Luca Guadagnino

It’s only natural that the director who brought us the aesthetically pleasing films Call Me By Your Name, Bigger Splash and I Am Love, among others, would himself exhibit a refined and quietly luxurious sense of dressing. During a photocall for his HBO series We Are Who We Are at the San Sebastian Film Festival, the Italian director kept things relatively simple in a red sweater, khaki pants and black loafers. Guadagnino allows the details of the outfit to speak for themselves, like the embroidered Loewe logo on the sweater, or the studded detailing of the loafers, near inconspicuous accents that, when noticed, communicate Guadagnino’s specific taste. The director then proceeds to top it all off with the pièce de résistance — a leather bucket hat.


As ASAP Nast heeds in his Instagram caption, “This look ain’t for kids.” The model consistently posts enviable fits, but this one, taken in October at the Bottega Veneta store, is difficult to top. Nast has long demonstrated an ability to pair traditional menswear pieces that are anything but traditional, like the above blazer and penny loafers paired with frayed jeans and a tattered netted shirt over a plaid vest. To add even more confusion, Nast throws a pearl necklace into the mix, making for a look that’s simultaneously preppy, punk and prim, one that in theory shouldn’t make sense but that Nast seamlessly pulls off. Because in a year when nothing makes sense, why should your clothes?

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