Will men wear bootcut jeans? One Esquire writer puts the look to the test
The verdict? Bootcut jeans are flattering, fashionable and ready for their renaissance
By 
AT DINNER RECENTLY, a day after Kendrick Lamar’s Super Bowl halftime show, a friend asked me, “What did you think of those jeans?” She hoped for an impassioned smackdown, but instead, I looked to his flares as the hybrid car of one of menswear’s biggest debates: baggy or skinny jeans? I shrugged, ¿Porque no los dos? On the other hand, I was also curious to see if the rapper was onto something; if a viral moment on the right celebrity would spur the masses into changing their pants silhouette, and therefore their personalities.
For starters, I knew I wouldn’t be able to get the same jeans Lamar wore past my thighs; they were designed by outgoing Celine creative director Hedi Slimane, a designer who favours lithe builds. They also cost $1,700. Its own can of worms, flared jeans for men are not readily available at retail, so I settled for a pair of bootcut jeans from contemporary Australian denim brand Ksubi. They may not have the polarising effect of flares, but when they arrive on my desk, I realise that even bootcut jeans are their own contrivance. I take them over to my colleague’s desk and ask for his input, holding the jeans up where they start to slightly flare at the knee. He tells me he wouldn’t wear them himself. Why? “It’s one of those things where you have to really own it. Otherwise it would look costume-y.”
Admittedly, even how I styled the jeans the next day felt a bit like a costume. My default uniform for work is pleated trousers with a rotation of shirts I use as my crutch. I wore the jeans with a slightly cropped dark grey T-shirt from Entire Studios, where its innovation lies in the torso darts that make the shirt drape into a V-shape. I’m not one for boots either, so I put on my croc-embossed Wales Bonner x Adidas Superstars. “I love this new look on you!” says a colleague. “It elongates the leg,” says another. It’s late in the week, and another colleague says that she thought this was casual-me. Of course, this is the fashion cognoscenti.
Curious to hear what others thought of the silhouette, while wearing my bootcuts, I did some market research. For Tanaka Chitete, a software engineer who owns no less than six pairs of bootcut jeans, it’s largely about “trying to figure out how to wear them with different types of shoes and different types of clothing.” Not having boots to wear with the jeans perhaps availed me from the retro look. Instead, a recent image of Pharrell in his bootcut jeans and Superstars informed my styling.
Chitete points to Lamar as an example, and how he paired his light-wash Celine flares with black and white Nike Air DT Max ’96s. “Because it’s very easy to just chuck on a pair of cowboy boots and be like, all right, cool, I’m good to go,” he says, “But the problem with that is you start to look as if you’re wearing a costume: cowboy ranch-hand, working man type stuff. But for me, [it’s about] trying to figure out how to wear them so I don’t fall into that trap.”
As a Gen Zer, I wasn’t old enough to have lived through the bootcut jeans trend of the early 2000s. Nor did I want to cosplay Serge Gainsbourg, one of Slimane’s major style influences. Pulling these on, however, was its own form of time travel (I did feel slightly yee-haw). But creative figures like Lamar and Pharrell are showing bootcut jeans in a contemporary light. Pharrell, the creative director of menswear at Louis Vuitton, also showed bootcut jeans in his autumn/winter 2025 collection last month in Paris.
What makes bootcut jeans so polarising is that they flirt with stereotype – that you’re ‘doing a thing’, making a statement, wearing something a bit ‘out there’. This is also true for most garments outside of the male norm, like white jeans, for example. Supremely, however, bootcut jeans, composed with a small percentage of elastane for stretch while fit slimmer around the thigh, bring with them a host of feminine associations.
Conservative detractors on X were too pleased to report that Lamar’s flared jeans were from the women’s section. In a retweet from menswear commentator Derek Guy, he pointed out that the conservative men criticising Lamar are themselves wearing slim-fitting trousers with stretch, “both of which were once considered strictly for women. In ten years, you’ll be in flares clutching pearls about something else.”
“That’s something that I do now,” Chitete says. “The women’s section is a lot more varied, a lot more interesting, the cuts are much more enticing . . . Every time I want to buy a brand new pair of bootcut jeans or anything wide, I always go to the women’s section because I can’t remember the last time I saw an advertisement for bootcut jeans as a lifestyle [piece] marketed towards men.”
Considering I haven’t worn jeans for two years after outgrowing my ‘perfect pair’, and how the bootcuts would flare out in a subtle cone shape, seeing (and feeling) these jeans give my legs an hourglass shape was the Thursday dopamine hit I needed. Heading out for my sweet treat that day, I started to hit my stride in the jeans, and they hit me back; the looser lower half slapped at the back of my legs as I walked. I felt activated by my clothing, and I loved it.
As I headed home, I completely forgot about the peak hour concert commute with Billie Eilish in town. At the train station, hordes of young fans were wearing bandanas and oversized football jerseys. For now, bootcut jeans may remain in the realm of the costume; unlike women’s fashion, for it to take one very famous figure to start a whole trend isn’t how most shifts in menswear works. But with Lamar being the headline-maker he is, bootcut and otherwise have reentered the conversation in a palatable way. Now, I’m a convert.
Related:
At the Super Bowl, Kendrick Lamar wore Celine flared jeans and custom Martine Rose
