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A quick litmus test to determine how cool you are: Where do you part your hair? If it’s on the side, bad news. Earlier this year, Gen Z TikTokers declared the side part over and the center part where it’s at. And if you swear by skinny jeans, profess a fondness for coffee or liberally use the laughing crying emoji, it gets worse: They’re also over.

As a geriatric millennial (the unfortunate term given to the micro generation born in the early 1980s) not using TikTok myself — and not entirely sure exactly what it is — I had to be informed of this news by younger, more digitally fluent acquaintances. Just take solace in knowing that Generation Alpha will eventually inform the Zers how mortifyingly middle-aged they are.

Cool as a concept is complicated. While easy to spot, it’s hard to define. It runs the risk of eating itself. For something to be cool, it must be desirable and popular but not everywhere (ubiquity is the enemy of cool). The shelf life of hotness these days is alarmingly quick. It’s nuanced and arbitrarily anointed — it could be new, it could be nostalgic — and what is the height of hipness to some is irrelevant to others. Some things are so desperately uncool that they double down on irony and become very cool (see: Crocs, once a prospect more terrifying than their reptilian counterpart and now, against all odds, a top trend). Like I said, it’s complicated.

Illustration by Klawe Rzeczy

But who decides what’s cool now? The glaringly obvious place to look is youth culture. Although the sands of style are forever shifting, it’s the younger generation that continually sets the agenda. Just as they catapulted miniskirts and bell bottoms to popularity during the 1960s youthquake and made grunge happen in the 1990s, the baton has now been handed to Gen Z to shape the cultural zeitgeist.

What separates this pack from their predecessors, however, is that they’ve grown up online. Social media has created a democracy of cool, with algorithms and swipes granting free access to a world of trends. “Because everybody gets a chance to share what they like, the masses decide what’s cool now,” explains Camille Charrière, the writer, tastemaker and fashion influencer with a whopping 1.1 million Instagram followers. “It used to trickle from the top down, but now it’s the opposite.”

Designer Harris Reed, whose duchesse satin ball skirt Harry Styles donned for his 2020 Vogue cover story, agrees. “I think what defines cool now is what everyone in the collective Internet universe is wearing, especially with everyone dressing up at home, posting their outfits of the day and playing with their identity,” he notes. “It’s this Internet generation that I find really interesting and inspiring as a designer myself.”

Digital dominance has effectively diminished the power of the old guard. “For generations, fashion magazines were the arbiters of cool,” says New York Times international styles correspondent Elizabeth Paton. “That power has been eroded by the relentless march of influencers and the ubiquity of access brought about by the digital age. Anything can be accessed anytime, anywhere.” Although that’s helped propel the growth of subcultures, it’s also led to “an even greater explosion in trend homogeneity,” she adds.

But what about the big-league fashion houses that were once the unimpeachable dictators of the dernier cri? If they play it right, they still have serious sway. Take Gucci, which topped the Lyst Index, the global fashion search platform’s compilation of the hottest brands and products, for Q1 of 2021. One reason the brand remains cool is that it’s constantly evolving, which bestows it with something priceless: relevancy.

To wit: Gucci has launched canny collaborations (Balenciaga, the North Face). It’s tapped into nostalgia by reissuing designs from Tom Ford’s tenure. It’s harnessed the power of the digital sphere, even releasing virtual sneakers with AR platform Wanna. It’s stepped away from the rigid catwalk calendar and aligned itself with inspiring ambassadors, like trailblazing septuagenarian model and activist Bethann Hardison. Gucci is coupling luxury with an indie spirit — and it’s working.

So you know where to look, but how can you be cool? We find an unlikely answer in celebrities. A new wave of cultural pioneers is broadening the notions of what influence looks like. Right now, cool is dependent on what you have to say, not what you’re wearing. According to data crunched by Lyst, Amanda Gorman, Harry Styles, Billie Eilish and Lil Nas X are among those currently setting the agenda. Case in point: Demand for red headbands increased 560% after Gorman donned a Prada one for the presidential inauguration. And page views for feather boas shot up 1,500% in the 48 hours after Styles wore three Gucci ones to the Grammys this spring.

All of them are champions of self-expression. Their cool is rooted in the fact that they aren’t trying to be anyone but themselves. But this irresistible allure of individuality is timeless. Consider, for instance, how 20-somethings have just “discovered” David Bowie and Princess Diana and now pore over archival images for inspiration. And on Cher’s 75th birthday in May, Instagram was flooded with images of her in all her resplendent, campy, not-for-anyone-but-me glory. Some of those looks were mocked when she first wore them. Today, they’re seen as totems of glamorous originality (just one reason why worst dressed lists feel like a relic of a lesser time).

Cher’s triumph is having fun with clothes. And that’s something we’re seeking in our fashion idols: levity, be it Marc Jacobs in platforms and nail polish or Tracee Ellis Ross owning every red carpet she sets foot on in pure fantasy couture. We’re increasingly drawn to people who take the things that matter seriously, but don’t take themselves too seriously. It’s why Dolly Parton — always an icon, now also a COVID-era hero thanks to her $1-million donation for vaccine research — is bestowed with a cool crown that will never be toppled by trends.

To be cool in 2021 is to be kind. It’s to connect, to go back to IRL life and, ironically, to realize that cool means both nothing and whatever you want it to be. Because as soon as you understand that style means nothing without substance, well, that’s the coolest thing of all. 

Read this article as it appears in the magazine.

Discover our roundup of new fashion icons making bold statements on red carpets, the streets and beyond.

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