The Best Celebrity Style Looks of 2020, Part One: The Before Times

Posted on December 28, 2020

A confession: Doing year-end style lists is not one of our favorite tasks. “Best Dressed” lists are a hoary old style-writing cliche that goes back too many decades and, if one is applying the usual agreed-upon standards of style critique, usually results in a boring or timid selection of looks that leans heavily conservative and appropriately elegant. This is why we’ve never called these lists “Best Dressed” and why we always try to populate them with risk-takers and exuberance. We reserve the right to choose and reward looks that would have made Coco Chanel retch, we’re afraid. Then again, she liked Nazis.

Our point is that the celebrity red carpet isn’t a Paris runway or a high society ball. It’s a promotional event that centers some of the most attention-seeking people in the world. As much as we may fawn and freak out over some Blanchett-esque vision of red carpet eleganza, at the end of the year, it’s the big, loud, look-at-me-dammit outfits that tend to stand out and delight us the most – this year more than most.

2020 provided us with yet another in a long list of conundrums this final week of the year because we really weren’t sure how we could approach this topic in a way that makes sense and honors the rather unique tone of the last 12 months. Yes, we all stayed home, including the celebrity set. Red carpets stopped being a thing entirely and for a time, no one in the celebrity style sphere quite knew how to react to the events around them. Like so many of us in 2020, stylists and celebrities figured out new ways of doing things and over time, we stopped seeing social media images of celebrities in sweatpants and started seeing more and more well-curated and photographed looks being modeled from the comforts of their own homes. But that, we’re afraid, is a story for another day, because you can’t do a 2020 style retrospective without acknowledging the part that most of us have forgotten in this decade-long year: for the first ten weeks of it, things were pretty much normal. More importantly: the time from January 1st, 2020 to just before we all switched to shoelessness as a daily style choice (mid-March) is typically one of the most fervently over-the-top periods on the red carpet calendar. Awards season, in other words. When we think of celebrity style in 2020, these are not the looks that spring to mind. In fact, most of the following looks were met with an incredulous “THAT was THIS year?” when we went through them. But yes, it all really happened and we feel like red carpet looks from the Before Times need to be remembered and considered in any year-end retrospective. To that end, we chose a rather idiosyncratic collection of ensembles all centered around one question. Remember when red carpets were these big, stupid-fun things that happened almost every day?


Jennifer Lopez in Valentino Couture at the Golden Globes

The very first red carpet look we covered in 2020 turned out to be the least prophetic. It is AMAZING to us that J Lo wore this in 2020. After all, she ended the year serving up looks that were decidedly less grandiose (if no less J Lo). Is this chic or elegant? No, not really. But GOD, do we miss seeing this kind of fashion on our front page; loud, tacky, diva drag fashion.

Speaking of which…


Billy Porter in Baja East at the Grammy Awards

Yes! Billy Porter wore this instant meme of an outfit THIS YEAR. It would have become iconic in any year, but the overwhelming “Keep your distance from me” vibe wound up becoming weirdly prophetic.




Meghan Markle (in Safiyaa) and Prince Harry at The Mountbatten Music Festival

While we’re more inclined to love the louder looks this year, attention must be paid to this, the ultimate “Eat it, bitches” look of 2020. For her last public appearance before jumping the royal ship and hightailing it home to mother with her prince and princeling in tow, Meghan Duchess of Sussex said goodbye to public life in England by stepping out in the loudest, most declarative and head-turning “You coulda had this” look she’s ever worn. Attaduchess.

And speaking of loud…


Tracee Ellis Ross in Zuhair Murad Couture at the Vanity Fair Oscar Party

Picking these lists is a process of elimination that takes a good deal of time. As we were deleting one selection after another in order to pare this down to a tight ten, we kept coming to this one and saying “We’ll come back to that.” In the end, it made the cut, when we’re pretty sure it never would have made it to the final rounds in a normal year. But we just love how big and bold and over the top it is. After ten months of covering a lot of caftans, pajamas and tasteful day dresses, this gigantic and borderline obnoxious frock just makes us smile. And it couldn’t be more perfect for her. You can’t tell us she didn’t love wearing this.


Anya Taylor-Joy in Vintage Bob Mackie at the “Emma” Los Angeles Premiere

Miss Anya had a great year, all things considered; kicking things off with the well-received Emma. (period included) and ending it with the even more well-received The Queen’s Gambit. But that’s not why this look made the list. We just loved the respect for fashion history. Bob Mackie doesn’t always get his due outside of recognition for his stagewear looks, but when it comes to the modern red carpet, he’s one of its chief inspirations. He more or less created the sheer, undergarment-baring gown that has become de rigueur in the last two decades  but was considered unfathomably vulgar back when Cher was pioneering them 45 years ago. He also made pioneering use of beadwork that would go on to inspire the work of countless designers for decades. This is not our favorite Mackie of all time by any stretch, but it’s so perfectly appropriate for her looks and the film she was promoting that you’d swear it was a garment custom made for her. A testament to how good he really was.


Kristen Wiig in Valentino Couture at the Oscars

It’s so fucking weird that we came around to loving it, maybe because it looks a little viral in design. Whatever the reason, at the end of 2020, we’re far more inclined to love the goofy, loud, risk-taking stuff. It wasn’t a year for subtlety.



Ariana Grande in Giambattista Valli at the Grammy Awards

This is one of those looks we’d probably have picked in any year, just because it represents a Personal Best for her while remaining very much in her branding zone. She doesn’t go for big poofy gowns all that much, but this one really suits her. It maintains that almost cartoonish princess vibe that she favors (the skirt is straight-up ridiculous), but the subtle shades of gray give it a feeling of sophistication that seems right for her at this point in her career. A step up in all the right ways – and an unforgettable look, to boot.


Lil Nas X in Atelier Versace at the Grammy Awards

We will always love our queer, Black, cowboy prince. This look is fucking amazing.



Charlize Theron in Louis Vuitton at the Costume Designers Guild Awards

Much like Tracee Ellis Ross’s golden eagle look further up, this rather retro and regal ensemble worn by Charlize to the Costume Designers Guild Awards just refused to get struck from our list, no matter how many times we came back to it. It has that loud, obvious, somewhat costumey vibe that is pushing our buttons right now, but we also love it because it’s not really her style and yet she looks fantastic in it. Like virtually all of the looks on this list, we’d quibble with some of the details, but the overall appeal and slight novelty make it a truly memorable look.



Zendaya in Tom Ford at the Critics’ Choice Awards 2020

And finally, a look we’re absolutely sure would’ve rated high (not that any of these are being ranked this year) on any year-end list compiled by us. Zendaya had a great, Emmy-winning, lucrative fashion contract-acquiring, career-defining sort of year and if we think about it too much, we may start crying over all of the eye-popping fashion she would have worn throughout all of it as she paraded in front of cameras, celebrating her success. Even then, we’re convinced this look would have stood out in the end. It’s just so memorable, so perfect for her, and so weirdly gorgeous that it can’t be denied. Not by us, anyway. We fully expect vehement pushback on nearly all of our choices this year, but what can we say? In the end, it was the stuff we’ve been missing the most that wound up looking the best to our eyes.

But don’t you worry. Our year-end style retrospective has only just begun. There will be caftans. And pajamas.

The Best Celebrity Style Looks of 2020, Part Two: Going Cazh for Lockdown


[Photo Credit: INSTARImages]

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