In the late-2000s, menswear saw a revival. Young men's interest in fashion was surging and propelled a number of trends to the fore. There was dash for suiting, endless queues for sneakers and droves of style obsessives converging at J.Crew, drinking an Americana Kool Aid. Stores like Self Edge and Unionmade pushed Japanese reproduction labels like Buzz Rickson and orSlow, and helped fuel interest in workwear and heritage brands like Red Wing and Barbour.

Workwear's influence on style certainly wasn't new during this time. But this period saw a massive shift in menswear trends toward raw denim and heavy Goodyear-welted boots, an overtly masculine 'lumbersexual' aesthetic and a general pursuit of a head-to-toe heritage look.

This wasn't the first time workwear ascended to popularity. Workwear had entered the zeitgeist in the '90s thanks to a buzzing skateboarding scene as well as artists like Wu Tang Clan, Tupac and Kurt Cobain. These style icons were birthed through surplus, vintage and workwear stores. But the rockstar aura — and the fame and fortune that come with it — distract from the fact that the local Army/Navy wasn't exactly their first choice when they were first entering the spotlight.

"When you would see your icons walking in the room and they got their Carhartt hoodie on, it's not because they chose to do that," designer Darryl Brown says. "It was a product of their environment." The stuff was cheap and durable. And for a typical skater or young artist, options were limited. But as they gained traction within pop culture, they brought their art and clothes with them.

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As streetwear and athleisure became more popular in the 2010s, startup denim brands went defunct and period-correct workwear was pushed aside.

But in recent years, there's been a shift back to workwear. Except this time around, it looks a little different. "It's more refined," says Tommy Dorr, who runs Moth Food, a vintage shop based in Los Angeles. "[Customers] may not know about the pieces they're buying, but they have such a great eye for color." He says that Carhartt is overwhelmingly popular with his customers these days. "I could sell Carhartt all day and never keep it in stock."

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The approach is less rigid than it was a decade ago. Workwear's proponents used to favor heritage brands and designers, practicing a sort of conservatism that eschewed both high and fast fashion, but today's micro-influencers like @withdnl and @fuegojoel frequently pair their vintage Carhartt Detroit jackets with Comme Des Garçons trousers and Nike Air Jordans.

Rare vintage pieces like WWII U.S. Navy Deck Jackets, which, in workwear's last revival, were likely to be paired with Japanese repro denim labels and brown leather engineer boots, are now thrown atop faded band tees and black Margiela boots. "If you look at the way people dress now, it's about mixing contemporary, archive designer and select vintage workwear," trend forecaster Samual Trotman says. "Sneaker culture has become such a big trend too and that has had a huge impact on the style."

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While sneaker culture has clearly influenced today's crop of workwear fans, the overall shift to a more eclectic, high-low mix of clothing is a sober departure from the maximalist attitudes and logo-frenzied trends in recent years. The average consumer is more knowledgeable, too.

Now, style is more about the low-key flex. "Workwear is interesting because it creates a subtlety that encourages the 'if you know you know' culture," costume designer Justin Boone says. "You can wear a look featuring artisanal brands like Visvim, Guidi, Greg Lauren, and David x Goliath that creates mystery because nobody can pinpoint exactly what you’re wearing unless they are already familiar. This feeling has brought a new level of excitement as everyone turned away from the heavily branded product era and gained more fulfillment in the need to be asked, 'where did you get that?'"

Though much of the trend has been menswear focused, it has shed some of the overt machismo of its previous incarnation. "It's definitely opened up the workwear trend to a wider audience now too because combined with the 90s styling it has a much more relaxed appeal and crosses genders too," Trotman says. "It's not wearing rigid denim, a Stetson hat and big leather boots. It's more about relaxed fits in washed and worn vintage fabrics that are comfortable."

Like workwear's pop-culture rise in the '90s, today's workwear found salience thanks to streetwear and hip-hop. "I think designers like Heron Preston really put a new focus on utility style when we first introduced his collaboration with NYC Sanitation Department in 2016," Trotman says. "This was really about fetishizing workwear uniforms and reevaluating what Americana meant again." Trotman also cites the importance of Raf Simons' short stint at Calvin Klein with his fireman jackets and the rise of brands like Fear of God and Billy Los Angeles that pushed wide-leg work-style pants with heavy canvas jackets.

Credit is also due to none other than Kanye West and his Yeezy collection. Dorr cites West as a major force in pushing lowkey workwear into the style space, recalling West's team making the rounds in various vintage showrooms for inspiration. West has also been known to sport Carhartt and Dickies on the daily.

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And it's not just high-fashion brands that have taken notice. Heritage brands have recognized their influence on the culture and leaned into it. Stan Ray pivoted its products to a more editorialized, streetwear aesthetic while other heritage brands are quick to collaborate with hot brands like Stussy and Awake NY.

At the height of this boundary-free workwear trend, the world was hit by COVID-19, changing the way people work and dress across the planet. With the pandemic, sweatpants and sweatshirts have exploded in popularity and denim sales have tanked. "Workwear has progressed and become extremely popular over the last few years," Boone says, "but I see it beginning to make its way out of popularity within the next few seasons."

But, Trotman thinks it's here to stay. "I feel like this iteration of workwear has much more staying power than before because its fits modern lifestyle better," he says. "Plus with everything going on in the world now and all the instability and fears around sustainability people are looking more and more to timeless garments that are both functional and high quality so that they last."