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

Posted on December 29, 2020

As we noted in part one of this series on 2020 celebrity style, the first ten weeks of the year proceeded fairly normally, offering us the typical level of celebrity attention-seeking through fashion, helped tremendously by awards season being in full swing. But around March 13th, the whole world shut down and for a good while after, we didn’t see much of the celebrity world, let alone the fashion one. By the time celebrities started wandering back in front of their cameras and social media accounts, they were fairly reluctant to come off looking grandiose or worse, out of touch (disastrous Imagine video debacle aside).

This uncertainty was compounded by a particularly intense and divisive election year as well as the massive social shift that occurred when Black Lives Matters protests sprung up all over the world. No one in the relatively frivolous worlds of high fashion and mass entertainment quite knew how to respond to the national mood, let alone continue the work of self-promotion. We were in the weird position of being off to the side of this particular matter while also being somewhat in the thick of it, as folks who depend on a steady string of celebrity fashion attempts for a good deal of our coverage but don’t actually work in the world of celebrity styling. This position never felt more perfectly represented than the moment one of the stars on this list called us up to set the record straight on why she was dressing the way she was, an event that never happened before in over a decade of celebrity style coverage and will almost certainly never happen again. 2020 was a weird one for everyone, you guys.

Our point is this: Just as we all began eschewing clothes with too many buttons, defined waistbands, hard shoes, or other such sudden un-necessities in 2020, so too did the stars. But because they’re stars – and because there’s a massive machine of promotion/entertainment surrounding their world, of which we are naught but a tiny yet fabulous cog – some of them managed to pull off their comfy fits in surprisingly high style. Others just managed to embody the way we all kinda felt this year, but in a particularly celebrity sort of way.


Sarah Jessica Parker, selling some shoes

We really admired how SJP tackled this year like a total New Yorker on the hustle. She’s had a successful line of shoes for years, but in early 2020, she opened her flagship store in New York, just as every store in the world shut its doors and every potential customer stayed home. She didn’t let a little thing like a worldwide pandemic and economic disaster slow her down, so as soon as she was able to, she was out in her store nearly every day, keeping the hustle going. She took mild issue with some of our coverage since it attributed a deliberateness to her paparazzi appearances that she didn’t think was quite fair, given that she had a business to support and employees she felt responsible for. We wound up having a lovely talk. As for this look, we loved it for being so of-the-moment and – from the cross-body bag to the headphones and backpack – so New York at a time when the city was really going through it. These may just be the best-styled pair of sweatpants we saw all year.


Tilda Swinton in Haider Ackermann at the Venice Film Festival

As Tilda Swinton ensembles go, we’re afraid we have to be honest and note that this one probably wouldn’t rate that high in any other year. But stepping out onto the streets of Venice in a pair of luxury pajamas just felt like one of those celebrity moments that summed up the year as a whole. She looks photogenic and comfy at the same time. What more could we ask of our stars this year?



Julia Garner in Chanel Couture at the Emmys

You might even say that Tilda kicked off a bit of a pajama trend – although fashion pundits were predicting one practically from the moment lockdown happened. It never truly took off as a fashion trend (which we predicted, since celebs, luxury brands and the stylists that bring them together are not in the business of projecting down-home relatability) although there were several notable attempts over the months. This rather chic Daisy Buchanan-esque take from Julia Garner by way of Chanel for the at-home Emmys was one of the more fabulous of the loungey looks this year.



Gabrielle Union in Christian Wijnants

But when it came to loungey, at-home, barefoot chic style, no one did it better and more often than Miss Gabrielle, who served up a veritable parade of chic, comfy, low-key looks that photographed amazingly well. This gigantic track suit is so fun and so perfect for the moment that it makes us smile every time we see it.



Jennifer Lopez in Ivy Park

Leave it to J Lo – by way of Beyoncé – to turn sweatpants and a hoodie into a moment as coordinated as a royal wedding or a Vogue September issue cover. You’ve gotta admit, no one else managed to make the quintessential 2020 ensemble look as good as this.


Chris Pine on a coffee run

To be fair, Chris Pine dresses like this all the time, but the slight randomness – not to mention comfort – of the white Birkenstocks paired with the face mask just made this feel more like the kind of thrown-together looks we’re all sporting on whatever tense little errands we had to do this year. Except he looks like Chris Pine and we don’t.



Rachel Brosnahan in custom jammies by Christy Rilling at the Emmys

Emmy nominee Rachel Brosnahan (with canine family members and husband Jason Ralph) sported the most chic and stylish pair of pajamas we saw all year, capping off the mini-trend so well that she may just have killed it. After all, it would take a lot to top a set of looks this stylish and photogenic.



Kerry Washington in Farm Rio

One of the things we begged celebrities and stylists to do early in the lockdown was to just snag some cute day looks and take a couple shots around the pool or the house. It took a while and a good deal of haranguing, but we think they may have taken our pleas to heart, because by mid-summer or so, we were seeing a whole lot of stylish caftans and summer maxi-dresses all over celebrity Instagram. Looking over the lot of them, this perfect end-of-summer frock worn by Kerry Washington with the absolute dead-perfect pair of shades is our favorite.


Meghan Duchess of Sussex Hanging out with Gloria Steinem

Meghan Markle, like so many of us, had her big plans for 2020 interrupted by events outside her control. While she and Prince Harry never quite got the chance to launch their new life in America in the manner they probably would have preferred, she managed to serve up quite a few moments of the new SoCal Sussex style in a series of at-home videos. While we tend to find the black-and-white filter use to be a bit too precious, we love the casual ease of the Duchess’ white t-shirt, wide-legged pants and straw hat. Add some sandals and chunky bangles and she’s serving an updated, minimalist sort of “Ladies of the Canyon” realness; a particularly on-point choice for a talk with a living icon.


Chris Evans reads us bedtime stories 



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Fine. It wasn’t a fashion moment. Whatever. You’re gonna argue with those forearms in a lumberjack shirt? Girl, please.


[Photo Credit: INSTARImages]

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