The Rise of Work Boots in Hollywood
Work boots, once considered the domain of construction workers and outdoor laborers, are now making a surprising appearance on the red carpets of Hollywood. A-list celebrities like Jennifer Lopez and Rihanna are embracing this rugged style, swapping their traditional dress shoes for something more durable and stylish. This trend has been embraced by several high-profile figures, including Timothée Chalamet and Austin Butler, who have been seen pairing classic workwear boots with tailored outfits, offering a relaxed alternative to formal attire.
Timothée Chalamet’s Bold Choices
Timothée Chalamet, known for his fashion-forward choices, made a strong statement at the Golden Globes in January. He wore a custom black velvet three-piece suit by Chrome Hearts, paired with matching black Timberlands. These boots were a gothic twist on the brand’s Premium 6-Inch waterproof boot, featuring silver Chrome Hearts hardware such as eyelets, aglets, and heel plates.
Timberland, the brand behind these boots, has a rich history rooted in workwear. Introduced in 1973 by the Abington Shoe Company in New Hampshire, the original “yellow” Timberland was designed for construction workers and outdoor laborers. Its innovative injection molding technique made it fully waterproof. By the 1990s, the style had become a staple in New York street style and hip-hop culture, worn by artists like Jay-Z and Nas.
Chalamet wasn’t the first to wear custom Chrome Hearts x Timberland boots. 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. Chalamet finished the outfit with a pair of orange Timberland work boots, complete with chunky lug soles and overlapping Chrome Hearts cross motifs.
Red Wing: A Cult Favorite
Another workwear brand gaining attention is Red Wing. Founded in 1905 in Minnesota, the company initially supplied sturdy leather boots to miners, farmers, and factory workers. Today, its moc-toe, lace-up work boots have developed a cult following. Austin Butler was spotted in a pair while promoting his crime thriller Caught Stealing in London, styling them with a chocolate-brown bomber jacket and distressed green corduroy trousers.
Chalamet has also been seen in Red Wings while promoting his Bob Dylan biopic, A Complete Unknown. His pair were the brand’s Classic Moc Toe boots, a style introduced over 70 years ago for hunting. Finished in Hawthorne Abilene leather, which develops a richer patina with wear, the boots feature a Goodyear welt sole designed for moving quietly across grass.
Red Wings have also caught the attention of other fashion enthusiasts. Jeremy Allen White was seen wearing the brand’s black leather 2964 Cooper Moc Toe boots, paired with straight-cut stonewashed jeans and an argyle cardigan. Ryan Gosling is known for favoring the label’s moc toe boots in buttery suede.
Beyond Menswear
The trend isn’t limited to menswear. Both Jennifer Lopez and Rihanna have incorporated chunky work boots into their off-duty wardrobes. Lopez regularly wears a pair of suede Brunello Cucinelli combat boots, while Rihanna has been seen in Bottega Veneta’s Haddock boots, which seem to have been borrowed from her long-term partner A$AP Rocky’s wardrobe.
Heritage Brands and Their Legacy
Several heritage shoemakers have been producing workwear boots for decades. Grenson, founded in 1866 in Northamptonshire, England, specializes in sturdy lace-up boots built using traditional Goodyear welt construction. Styles like its Fred and Brady boots, with thick rubber soles and robust leather uppers, are versatile enough to pair with tailoring.
R.M. Williams, founded in 1932 in Adelaide, Australia, is another iconic brand. Known for its sturdy leather boots designed for life in the outback, the brand’s signature Chelsea boots, particularly the Craftsman, remain the best-known design. Each pair is cut from a single piece of leather and assembled largely by hand.
Allen Edmonds, founded in 1922 in Wisconsin, is best known for its classic Oxfords and loafers. However, the American shoemaker also produces rugged lace-up boots inspired by traditional workwear and military styles. The Higgins Mill, introduced in 2016, has become one of the brand’s most popular models due to its thick leather uppers and sturdy Dainite or lug soles.
For those looking to embrace the trend, swapping dress shoes for work boots can instantly give a more relaxed, low-key feel. With Timothée Chalamet’s endorsement, you know you’re on the right track.
