The Style Trends to Watch for in 2020, According to the Insiders

With insight from designers, trend forecasters, vintage dealers and more.


It’s hard to make sense of what’s going on in today’s fashion free-for-all landscape. But there are some common threads woven throughout the runways (and Instagram) that you’ll likely see a lot of this year. To make sense of it all, we had industry insiders polish off the crystal ball and give us their takes on what’s to come for 2020. The clairvoyants we sought ranged from designers, trend forecasters, vintage dealers and more.

The ’70s and the 2000s

Fashion recycles its way through the decades, and the formative years of both baby boomers and their children are en vogue. The 1970s comeback is less disco and more Woodstock, with earth-tones and flared pants. And it’s strutting down the street alongside leather shirts and cardigans, an interesting pairing of hippie and grunge.

Jon Feldman, owner of Grand Street Local: “In the shows and from a vintage perspective, I’m seeing a lot of the ’70s come back. But, it’s not so much of the disco vibe.”

Suits, but not necessarily for a boardroom meeting

The era of the tightly tailored suiting is not what we’re talking about. Rather, streetwear is kicking itself to the curb and is headed to the tailors with a subversive eye, rendering business and formal attire in relaxed proportions and avant-garde construction. Either way, there’s still an evident move toward sophistication. The Hypebeasts are growing up.

Chris Black, writer and creative director, Done to Death: “The pendulum always swings. At the runway shows, there was a lot more suiting, a lot brighter colors. Relaxed suiting, bright colors and different materials. [Designers] are sending models down the runway in pieces that didn’t have lapels, but it was still a suit with proper buttons. A Cold Wall showed suits, Virgil showed a suit.”

Jermy Kirkland, host of the podcast, Blamo!: “Streetwear dudes are returning back to the basics. There seems to be a return to classic style and a rebellion against the super casual. Like, the new hires are dressing better than the CEOs.”

Antonio Ciongoli, designer of 18east: “I do feel the tide shifting at the top back towards tailoring and it’s been interesting to see how that plays out in the neighborhood around our studio. The vibe is very different from the soft-shouldered, Italianate silhouette that characterized the last tailored wave of the early 20-teens. It feels more rooted in vintage, which is its own trend and could — and hopefully does — stem from the realization that we should be wasting less.”

Menswear is getting sexy

Crop tops, low rise jeans. They’re back! They’re not for everyone, but then again, not even the great blue jean can say it has a 100 percent success rate.

Jon Feldman: “A few weeks ago, I bought a pearl necklace… There are a lot more risks that are being taken and I feel like there are a lot more things that are acceptable in the world nowadays.”


Fanny packs and sacoche-style cross-body bags were big trends in the past several seasons. Coinciding with the interrogation of gender-norms and a more modern masculinity, these handy accessories have gone all the way into full-fledged purses. And why not? Bags are inherently functional. Function is form. And form, function. While we’re at it, why not make it look cool, too? Whatever you do with it, just don’t call it a murse.

Chris Black: “A lot of purses for men. A lot of handbags for men… Different sizes and shapes, worn under a coat, worn out.”

Micro trends over macro trends

There have never been more fashion tribes than now. The push and pull of silhouettes from wide to skinny to wide again will always happen, but Amy Leverton says that today’s fashion landscape is so fraught with individual styles that it’s hard to pinpoint one overarching trend. Rather, there are dozens of micro trends. In contrast to basic jeans, self-made DIY brands on platforms like Instagram and Depop are customizing and upcycling denim in wildly outlandish ways — and they’re successful.

Antonio Ciongoli: “What’s funny about trends at a time where everyone is basically mainlining hyperspecific content based on their interests is that it feels like everything is cool to somebody.”

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Bigger silhouettes

From straight leg to relaxed to straight-up massive, guys are looking for more legroom.

Chris Black: “Volume. Things are bigger. I think the tiny thing is kind of over. I think we’re going big again, whether it was a bag or a fit.”

Amy Leverton: “I’m seeing some absolutely massive silhouettes. Loads of brands like Anglan from South Korea are going with huge, huge silhouettes.”

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