From Timberland to Red Wing, work boots have become an unexpected favorite in Hollywood – Jennifer Lopez and Rihanna are among those leading the trend
Your favorite fashion rebels are leaving their high heels behind for more durable footwear.A-listers from Timothee ChalametAustin Butler has been combining traditional work boots with tailored clothing, opting for a more casual style instead of conventional formal wear.
Chalamet, who has become one of the most closely followed figures in men’s fashion, presented a compelling argument this year at the event.Golden Globes in January, combining a custom black velvet three-piece suit from the Los Angeles brand Chrome Hearts with a matching set of black Timberlands. The boots, developed in partnership with Chrome Hearts, offered a gothic interpretation of the brand’s Premium 6-Inch waterproof boot, featuring silver Chrome Hearts hardware such as the eyelets, aglets, and heel plate.
Timberland has a rich history tied to workwear. The popular waterproof leather boot was first launched in 1973 by the Abington Shoe Company, based in the U.S. state of New Hampshire. Designed for construction workers and those engaged in outdoor labor, the original “yellow” (warm tan) Timberland was created using a groundbreaking injection molding process that attached the sole to the upper, ensuring complete waterproofing. By the 1990s, the design had evolved beyond its original purpose, becoming a key element of New York’s street fashion and hip-hop scene, worn by artists such as Jay-Z and Nas.
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The Golden Globes wasn’t the first occasion when Chalamet wore custom Chrome Hearts x Timberland boots this past year. At the Los Angeles premiere ofMarty SupremeLast December, he and his girlfriend Kylie Jenner made an appearance in coordinated custom orange leather ensembles from Chrome Hearts, with Chalamet completing the look by wearing a pair of orange Timberland work boots featuring a thick tread sole. These boots also included overlapping Chrome Hearts cross designs – one made from a fluffy orange-and-black material that resembled tiger fur – along with silver accents such as speed hooks, eyelets, and aglets.
Another brand known for workwear making an appearance in the celebrity scene is Red Wing. Established in 1905 in the Minnesota town of the same name, the company initially provided durable leather boots to miners, farmers, and factory employees throughout the American Midwest. Over a hundred years later, those same long-lasting designs—especially the company’s moc-toe, laced-up work boots—have gained a devoted fan base.
Austin Butlerleft in a pair in August last year while promoting his crime thrillerCaught StealingIn London, pairing the rugged boots with a chocolate-brown bomber jacket and worn green corduroy pants.
Chalamet has also been seen wearing Red Wings while promoting his film about Bob Dylan,A Complete UnknownHis boots were the brand’s Classic Moc Toe model, a design that originated over 70 years ago for hunting purposes. Crafted from Hawthorne Abilene leather, which is said to become more vibrant with use, these boots feature the brand’s signature high-cut silhouette and a Goodyear welt sole that allows for quiet movement on grass.
The Red Wings have also drawn the interest of other fashion enthusiasts, such as Jeremy Allen White, who was spotted wearing the brand’s black leather 2964 Cooper Moc Toe boots, paired with straight-fit stonewashed jeans and an argyle sweater while buying flowers at his neighborhood store. Ryan Gosling, on the other hand, is often seen opting for the label’s moc toe boots in soft suede.
The trend extends beyond men’s fashion as well. Jennifer Lopez and Rihanna have both been seen adding chunky work boots to their casual outfits. Lopez often wears a pair of suede combat boots from Brunello Cucinelli, while Rihanna has been spotted in Bottega Veneta’s Haddock boots – a pair that appears to have been taken fromher long-term boyfriend A$AP Rocky’s wardrobe.
In addition to these popular celebrity choices, several traditional shoemakers have been crafting workwear boots for many years. Established in 1866 in Northamptonshire, located in England’s East Midlands, Grenson is one of the country’s oldest shoe brands and has consistently focused on durable lace-up boots made with classic Goodyear welt stitching. Models like the Fred and Brady boots, featuring thick rubber soles and strong leather tops, draw inspiration from traditional work styles while being adaptable enough to go with formal attire—Stephen Graham and Holly Willoughby are both admirers.
Some of the most recognizable work boots come from R.M. Williams. Established in 1932 in Adelaide, South Australia, by outdoor enthusiast Reginald Murray Williams, the company gained its fame through durable leather boots created for life in the wilderness. The brand’s famous Chelsea boots—especially the Craftsman model—are its most recognized style, with every pair made from one piece of leather and mostly hand-assembled.
Another traditional brand with strong ties to workwear is Allen Edmonds. It is most famous for its classic Oxfords and loafers – worn by the likes ofactors Paul Newman, Daniel Radcliffe and Ryan Reynolds, and US presidents Ronald Reagan and George H.W. Bush – the American shoe company, established in 1922 in Wisconsin, also creates durable lace-up boots influenced by traditional labor clothing and military designs. The Higgins Mill, launched in 2016 but based on classic American service boots, has emerged as one of the brand’s top-selling styles, thanks to its thick leather tops and strong Dainite or treaded soles.
For individuals considering joining the trend, exchanging formal shoes for boots can immediately create a more casual, laid-back yet versatile vibe. Plus, with Timothee Chalamet’s endorsement, you’ll be confident you’re making the right choice.
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This piece was first published in the South China Morning Post (www.scmp.com), a top news outlet covering China and Asia.
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