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The Men Who Wear Workwear Well

To nail the off-duty trend, look to Mr Kanye West, Mr Shia LaBeouf and more

When Mr Kanye West showed up at this year’s Met Gala, he wore a Dickies jacket that reportedly cost less than $50. It was not in line with the Camp: Notes On Fashion dress code (or, was it?). Nor did it conform to the event’s unofficial dress code: expensive. But there was something satisfyingly anti-establishment about the fact that in a room full of people wearing suits and dresses – the combined value of which could probably purchase a small Pacific island – Mr West wore a jacket that was otherwise unremarkable.

But it is 2019 and overalls, chore jackets and hiking boots are fashionable. Clothing originally intended for dockhands, fishermen and construction workers is now being worn by actors and rappers (and stylists and editors, but who cares about them?). This is the kind of stuff almost anyone can wear with ease, but there are those who make workwear work. Here are some of the men who have done it best.

Sir Daniel Day-Lewis

  • Sir Daniel Day Lewis in New York, March 2019. Photograph by The Mega Agency

Last year, at the age of 62, Sir Daniel Day-Lewis managed to reinvent himself as a fashion icon when his workwear-heavy style was picked up by Twitter. Was Sir Daniel, tweeters wondered, a closet hypebeast? Probably not, but his unfussy yet cool approach, exemplified here by twill trousers (note the rivets), wraparound sunglasses and some hiking-type sneakers, could have fooled us. It’s resolutely daddish and we’re picking up what he’s putting down.

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  • Jacquemus Wide-Leg Cotton-Corduroy Cargo Trousers

Mr David Alan Grier

  • Mr David Alan Grier in Los Angeles, March 2019. Photograph by Getty Images

Dungarees are the hardworking cousin of the jumpsuit and thus not the easiest thing for a grown man to pull off. The comedian and underrated style savant Mr David Alan Grier has done a brilliant job here and looks very comfortable in them. An outfit like this could easily veer into slovenly trucker territory, but the details elevate it to something much greater. Note the sunglasses tucked into the chest pocket, the subtle contrast of the blue denims and the cherry-on-top addition of the bright red cap.

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  • Balenciaga Logo-Embroidered Cotton Baseball Cap

Mr Shia LaBeouf

  • Mr Shia LaBeouf in Los Angeles, November 2018. Photograph by Mr Clint Brewer/Backgrid

One thing to remember about Mr Shia LaBeouf: this is a man who can wear dirty turquoise Crocs and still find a swell of fans who swear he’s one of the most stylish men on the planet. Perhaps he’s a great workwear hero because his outfits always look so practical. He gives the impression that he wears beige scuffed boots not because they are in fashion, but because they’re comfortable and good for walking in. Which is an incredibly fashionable reason to wear something nowadays.

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  • John Elliott The Cast 2 Slim-Fit Distressed Selvedge Denim Shorts

A$AP Rocky

  • A$AP Rocky in New York, June 2016. Photograph by Mr Robert Kamau/Getty Images

You might reasonably assume, thanks to fashion’s recent appropriation of workwear, that A$AP Rocky nabbed these blue trousers with reflective orange strips from a Paris Fashion Week runway. They are, in fact, standard-issue firemen’s trousers from Dickies, but A$AP has magically transformed them into something satisfyingly streetwise (note the coordinating orange belt). The fact that he’s tucked in his long-sleeved Vlone T-shirt smartens the whole thing up and, before we know it, we’ve witnessed a masterclass in making actual workwear look like wildly expensive streetwear. That’s talent.

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  • Billionaire Boys Club Cotton-Blend Cargo Trousers

  • Heron Preston 4cm Logo-Jacquard Webbing Belt

Mr Eddie Redmayne

  • Eddie Redmayne in London, May 2019. Photograph by Backgrid

There’s nary a more useful item in a man’s wardrobe than the French workwear jacket, also known as the chore jacket. Good to have on hand whatever the weather, it’s that rare piece of clothing that truly toes the line between smart and casual. Here, the always dashing Mr Eddie Redmayne is wearing one paired with selvedge denim jeans, another hardworking item. It is, in no uncertain terms, a perfect outfit for the weekend.

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  • Holiday Boileau Wool-Blend Jacket

  • A.P.C. Petit New Standard Skinny-Fit Dry Selvedge Denim Jeans

Mr Ryan Gosling

  • Mr Ryan Gosling in Los Angeles, October 2017. Photograph by Shutterstock

Hey, girl, check out my denim jacket. Blue chinosRed Wing Shoes and the aforementioned denim jacket Mr Ryan Gosling is wearing make for a trifecta of workwear style topped off expertly with a pair of Persol tortoiseshell sunglasses. Mr Gosling’s cool factor is helped out by the fact that he seems to be flanked by multiple bodyguards in this photograph, but with or without a gaggle of heavies, it’s an undeniably good look.

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  • KAPITAL Denim Trucker Jacket

  • Red Wing Shoes 875 Moc Leather Boots

Mr Kanye West

  • Mr Kanye West in Bel Air, November 2018. Photograph by Backgrid

Most men would not think to coordinate their hair with their outfit, but Mr Kanye West is not most men. In a violently bright red Carhartt WIP jacket with a contrasting collar, he’s also sporting a rose-tinted barnet. Add in the grey cotton-canvas trousers, which temper the red of the jacket nicely, and his status as a workwear style god is cemented. We also like this picture because he looks happy, and pictures of Mr West smiling are rare. Call it resting Ye face.

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  • Stone Island Logo-Appliquéd Brushed-Cotton Overshirt

  • Valentino Pleated Logo-Print Tech-Jersey Cargo Trousers

Mr Brooklyn Beckham

  • Mr Brooklyn Beckham in New York, January 2019. Photograph by Mr James Devaney/Getty Images

Mr Brooklyn Beckham, like any other 20-year-old, looks good in whatever he wears, but he’s really making a case for Gen-Z workwear here. The starched Dickies that are meticulously cuffed so that they reach just above ankle height over his Converse sneakers are *chef’s kiss*. There’s mess here, but there’s also brilliance.

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  • Engineered Garments Patchwork Cotton-Corduroy Trousers

  • Converse Chuck 70 Canvas High-Top Sneakers

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