What do Kendrick Lamar, Pharrell Williams, Lenny Kravitz and Benson Boone all have in common? Show-stopping Grammys performances, yes. But we’re talking off stage. They’re all early adopters – and, in some cases, long-term devotees – of the bootcut jean, a divisive denim silhouette that’s back to shake things up for 2025.

You can pinpoint the moment that bootcut jeans went viral back to Lamar’s Super Bowl halftime show in February. Working with stylist Taylor McNeill, the Compton-born rapper was seen hopping onto the bonnet of a vintage Buick while sporting a pair by CELINE HOMME, teamed with a varsity jacket and Nike sneakers. Following the performance, which drew in a record-breaking 133.5 million viewers, Google Trends showed that bootcut jeans saw a significant upswing in terms of searches.

Bootcuts actually go way back to the 1870s, when they found their form and function. It was then, originally influenced by the naval-cut trousers of the 1850s, that Levi’s began making men’s jeans that were looser at the shins and ankles to allow room for cowboy boots.

The jeans found their calling in the 1960s and 1970s thanks to hippies, who wore wide-leg bell-bottoms while spreading good vibes. At the same time, the likes of Yves Saint Laurent, Bob Mackie and Serge Gainsbourg made pooling jeans a part of their uniforms. The flare became associated with the eccentricity of dandies (no doubt something we’ll see a lot of at this year’s Met Gala), as exhibited in Malick Sidibé’s portraits from the mid-1960s and Samuel Fosso’s photographs of the 1970s.

But bootcuts and flares fell to the wayside, becoming inherently uncool in the 2010s. Enter the viral Tumblr account JeansAndSheuxsss, which threw shade at people wearing jeans – almost always bootcut – with formal shoes. It all but sounded the death knell for bootcuts and they became a marque of older generations striving to relive their sartorial heyday.

Now, thanks to Lamar et al’s backing, bootcut jeans appear to be having a moment. But for anyone who has been observing the state of men’s fashion for some time, this won’t come as a surprise. This cut has been doing the rounds for the past couple of seasons, steadily plotting its comeback.

Lamar’s own jeans were actually first seen in 2019, as part of Hedi Slimane’s SS20 collection for CELINE HOMME, while Alessandro Michele was an early advocate for the style during his tenure at Gucci.

Meanwhile, as N.E.R.D fans will verify, Williams has been an avid wearer of loose cut jeans of gargantuan proportions for many years. Recently, he’s been spotted styling his light-wash, bootcut jeans with a chore jacket, baseball cap and “dad” sneakers. “I think his AW24 show for Louis Vuitton was a turning point in bringing back bootcut jeans on a mainstream level,” says Adrien Communier, style editor at GQ France, on the influence the brand’s men's creative director has had on this silhouette’s revival.

Of course, Lamar and McNeill have demonstrated that they look equally good with sportswear. Sneakers, a sports jacket, a generous amount of bling and a backwards cap gave the bootcut a cooler 2025 spin. Singer-songwriter Boone, meanwhile, has really run with the trending cowboy aesthetic, sporting bootcut jeans hoisted up with chunky western hardware belts. Timothée Chalamet, who is also styled by the aforementioned McNeill, wears his flares baggy and loose, pairing them with his signature scarves and striped tees.

Take a look at the streets of London, New York and Paris and you’ll see that plenty of guys – those with a heightened interest in fashion, who carry their cigarettes in vintage tin trays – have been wearing bootcut jeans of late. “The all-Americana and western heritage aesthetic combined with a never-ending interest of vintage fashion created an opening for the bootcut to come back,” Communier says.

Holly White, stylist of Joe Locke, Luke Newton and Corey Mylchreest, is all for bootcut jeans. “I haven’t got them on anyone yet, but I’m dying to,” she says. “They can be super flattering and chic on many silhouettes.”

Her advice is to add a boot and shirt to lean into the “cowboycore” vibe or go “retro, à la Kendrick Lamar”. If you’re still somewhat daunted by the silhouette, a fine knit, leather jacket and Chelsea boots will keep things low-key enough to still feel like “you” while debuting your bootcuts.

For those who are all in, look to hype brands such as AMIRI and ERL, who have been pushing bootcut silhouettes down the catwalk. Meanwhile, cult labels from KAPITAL to Our Legacy have put them at the forefront of their seasonal drops.

Multidisciplinary artist Andrew Georgiades, a regular at fashion week and avid shopper, is all for bootcut jeans. “There’s something about how bootcut jeans fall on your footwear that feels nonchalant, masculine, lived-in and carefree,” Georgiades says. “While being harder to style, done correctly, they can add sex appeal to your outfit.”

Communier believes that the upward trajectory of the flare will continue. “For the past years, menswear was centred around trousers that were large and oversized, but the silhouette is slowly coming back to something more fitted with the bootcut flare at the bottom.” Do with this information what you will.