Your favourite red carpet rebels are swapping out their dress shoes for something more rugged. A-listers from Timothée Chalamet to Austin Butler have been pairing classic workwear boots with tailoring, sidestepping tried-and-true formal attire for a more relaxed approach to dressing.

Chalamet, who has emerged as one of menswear’s most closely watched dressers, made a strong case at this year’s Golden Globes in January, pairing a custom black velvet three-piece suit by Los Angeles label Chrome Hearts with a matching pair of black Timberlands. The boots, created in collaboration with Chrome Hearts, were a gothic take on the brand’s Premium 6-Inch waterproof boot, finished with silver Chrome Hearts hardware including the eyelets, aglets and heel plate.

Timberland itself has a long history rooted in workwear. The much-loved waterproof leather boot was introduced in 1973 by the Abington Shoe Company, in the US state of New Hampshire. Intended for construction workers and outdoor labourers, the original “yellow” (warm tan) Timberland was built using an innovative injection moulding technique that fused the sole to the upper, making the boot fully waterproof. By the 1990s the style had taken on a new life far beyond job sites, becoming a staple of New York street style and hip-hop culture, worn by artists like Jay-Z and Nas.

The Golden Globes wasn’t even the first time Chalamet wore custom Chrome Hearts x Timberland boots in the past year. At the Los Angeles premiere of Marty Supreme last December, he and girlfriend Kylie Jenner arrived in matching custom orange leather looks by Chrome Hearts, with Chalamet finishing the outfit with a pair of orange Timberland work boots complete with chunky lug sole. This pair also featured overlapping Chrome Hearts cross motifs – one rendered in furry orange-and-black material reminiscent of tiger skin – alongside silver hardware including speed hooks, eyelets and aglets.

Another workwear brand turning up on the celebrity circuit is Red Wing. Founded in 1905 in the Minnesotan town of the same name, the company originally supplied sturdy leather boots to miners, farmers and factory workers across the American Midwest. More than a century later, those same hard-wearing designs – particularly the company’s moc-toe, lace-up work boots – have developed a cult following.

Austin Butler stepped out in a pair in August last year while promoting his crime thriller Caught Stealing in London, styling the rugged boots with a chocolate-brown bomber jacket and distressed green corduroy trousers.

Chalamet, too, has been spotted in Red Wings while promoting his Bob Dylan biopic, A Complete Unknown. His pair were the brand’s Classic Moc Toe boots, a style first introduced more than 70 years ago for hunting. Finished in Hawthorne Abilene leather, which supposedly develops a richer patina with wear, the boots have the brand’s distinctive high-cut profile and a Goodyear welt sole designed for moving quietly across grass.