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The 10 Best Bootcut Jeans for Men Make the Ultimate Fashion Statement

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During Men’s Paris Fashion Week for the Fall 2024 season, there was one show that stood out, shaking—if not breaking—the Internet. It was Pharrell Williams’s third offering at Louis Vuitton, which took a page from the Yeehaw Agenda and interpreted the house’s iconic codes through the lens of Black and indigenous Western Americana. It was a celebrity-packed ode to true cowboys, complete with artistic collaborations with creative director Dee Jay Two Bears of the Standing Rock Sioux Tribe and the viral Timberland LV boot. Another standout from the collection, one rooted in Western culture, was the parade of updated takes on bootcut jeans. Washed-out, ’70s-inflected, intricately embroidered, or featuring worn-in patchwork: The distinct style of denim was in abundance.

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Williams’s bootcut jeans have come at a moment when the relaxed, slightly flared fit is having an undeniable comeback in the fashion industry. “The resurgence of bootcut jeans is the natural progression of last year’s ’90s trend, moving into the naughties,” explains Thom Scherdel, menswear buyer at Browns. “There are brands that are really championing the style, from Y/Project with heavy washes to Our Legacy resurrecting fits from seasons gone by to Marni providing a contemporary take on the bootcut.”

Bootcut jeans are intrinsically laid-back, built to slouch just right at the hem. They also happen to be incredibly flattering. And now that they’ve returned to the fashion fold, springing back from their heyday in the early 2000s, it might be time to invest in a new pair.

But where to start when looking for the ideal bootcut jeans for the modern era? We’ve got you covered. Below, find our guide to the best bootcut jeans from brands that truly specialize in the style, the ones with decades—and in some cases, centuries—of experience refining, crafting, and delivering cowboy cuts.


The Anatomy of Bootcut Jeans

The bootcut jean differentiates itself from other denim styles in a handful of key ways. Primary among them is the silhouette, which is cut straight from the thigh to the knee with a slight flare at the ankle. The flare is subtle, while the widening is gradual and discrete, creating just enough room for, well, boots. But it also serves as a suitable frame for your go-to loafers or trainers: The hem typically rests at the ankle, puddling over flat shoes for a casual look. Also, traditional bootcut jeans have a high-rise waist, but a number modern interpretations feature low-rises that sit just below the hip. As for the overall fit, the best options should moderately hug the leg. It shouldn’t feel tight or constricting.


A Brief History of Bootcut Jeans

We can trace the origins of bootcut jeans back to the 1870s, when Levi’s manufactured denim trousers accommodated the lifestyle of the off-duty military, linemen, cowboys, ranchers, and vaqueros. By the 1920s, Wrangler (neé Blue Bell) and Lee followed suit. Building upon the functionality for those at home on the range, Wrangler introduced its Cowboy Cut in 1947, the reputed first bootcut jean, the standard model, a design that’s still manufactured today.

Then, with the advent of the Hollywood Western, the style broadened its consumer base. Bootcut jeans were no longer relegated to rodeos, farms, and corals. To wit: The ’60s had stars such as Steve McQueen and Robert Mitchum strutting down the streets of Tinseltown wearing Wrangler’s wares.

Simultaneously in the Age of Aquarius, hippies made the bootcut their own, adorning them with patches, embroiders, and bright colors. The flair also began to expand, and by the ’70s, the bell-bottom took center stage. Bootcut jeans, generally, went into hibernation in the next few years, taking a back seat to the straight-leg styles that dominated the ’80s and ’90s.

It wasn’t until the early 2000s when bootcut jeans experienced a renaissance. Indeed, the Y2K era became synonymous with the fit. Who can forget the many US Weekly images of Ashton Kutcher sporting distressed bootcut jeans and a seemingly endless array of Von Dutch trucker hats; a buzz-cut, soccer-playing David Beckham in double denim—with the pants being bootcut, of course; and A-listers from Harrison Ford to Justin Timberlake turning up on, yes, the red carpet in the popular style. It’s worth noting that this period was also the height of the designer-denim phenomenon. Brands like Citizens of Humanity, Rock & Republic, and True Religion sprung up and quickly dominated a fast-growing market. Their collections were loud, at times bedazzled. Their jeans became a status symbol, with bootcut being the preferred silhouette. The stars were wearing them, and so were the masses. But as is always the case in fashion, there was a seismic shift.

The 2010s saw the return of punk and, as a result, the influx of skinny jeans. Again, the bootcut styles largely left the fashion lexicon. And things stayed this way until designer Demna showed just-faded bootcut jeans at the Balenciaga Spring 2019 show. This was also around the time when fashion from the early aughts started to fall back into favor. Now, labels like Marni, Y/Project, Egonlab, and luxury behemoth Louis Vuitton are exploring Y2K’s favorite style of denim. And while some of us may still cringe at the thought of having worn Von Dutch caps and Ed Hardy shirts, the history of the bootcut extends well beyond that time frame.


The 10 Best Men's Bootcut Jeans of 2024: Buying Guide
The 10 Best Men's Bootcut Jeans of 2024: Buying Guide

BEST CLASSIC BOOTCUT JEANS

Wrangler Cowboy Cut Original Fit Jeans

Buy Now on Wrangler: $55

No exploration of the best bootcut jeans would be complete without the original—and arguably the definitive—design. Introduced in 1947, Wrangler’s Cowboy Cut is durable, rugged, and as classically masculine as it gets. The traditional high-rise waist, which elongates the leg, and slight, subtle flare specifically built to fit over footwear with a long shaft are textbook. This doesn’t mean it won’t pair nicely with Chelsea boots (especially Bottega Veneta’s Ripley) or a low-top sneaker. It’s also the official ProRodeo competition jean: The links to Western culture are legit. Above all, the fact that the Cowboy Cut hasn’t changed much since the ’40s is a testament to its timeless appeal.

Date of Brand Origin: 1904.
Washes Available: 10.



The 10 Best Men's Bootcut Jeans of 2024: Buying Guide
The 10 Best Men's Bootcut Jeans of 2024: Buying Guide

MOST DURABLE BOOTCUT JEANS

Levi’s 517 Bootcut Jeans

Buy Now on Levi's: $70

Levi’s is the OG denim brand. And though Wrangler is credited for creating the original bootcut jean, Levi’s has offered styles with flared legs for decades. Take the 517, which was developed in 1969 as a core design made to fit over boots. It is crafted from 100 percent cotton, meaning that it is real-deal denim—read: no stretch. It’s built to last. It’s also cut to sit at the waist with a fitted thigh and a just-barely visible bootcut leg. Indeed, the flare is minimal, making it an ideal option for a good loafer. 

Date of Brand Origin: 1853. 
Washes Available: 6.



The 10 Best Men's Bootcut Jeans of 2024: Buying Guide
The 10 Best Men's Bootcut Jeans of 2024: Buying Guide

MOST VERSATILE BOOTCUT JEANS

Lee Legendary Regular Bootcut Jeans

Buy Now on Lee: $46

Lee may be the third all-American denim original, but this doesn’t make it any less worthy of praise. The brand, which took up jean-making in 1912, has its heart in workwear and factory overalls. But when it introduced Westerners—a slim, dressed-up bootcut—in 1958, it became the go-to brand for many Southern gents and authentic cowboys. Today, Lee offers not one but four categories of bootcut jeans: Legendary, Extreme Motion, Heritage, and the Modern Series. But topping our list is Legendary, which is available in 10 classic washes so you can pick the preferred shade to match your shirt and accessories. 

Date of Brand Origin: 1912.
Washes Available: 10.



The 10 Best Men's Bootcut Jeans of 2024: Buying Guide
The 10 Best Men's Bootcut Jeans of 2024: Buying Guide

BEST SUSTAINABLE BOOTCUT JEANS

Citizens of Humanity Milo Classic Bootcut Jeans

Buy Now on Citizens of Humanity: $258

Buy Now on Nordstrom: $258

L.A.-based Citizens of Humanity—founded by 7 For All Mankind’s cofounder Jerome Daham in 2003—is a true 2000s denim hero. Who can forget the sea of images of everyone from Halle Berry to Tom Hanks out and about in their favorite pairs? The brand has been offering relaxed, tasteful bootcuts since the beginning, most of which are made of 98 percent cotton with a slight stretch for comfort. Today, Citizens of Humanity is also investing heavily in sustainable agriculture, an added bonus for anyone looking to feel as good as they look. Slide into the Milo Classic Bootcut in a slate-blue vintage hue for a style that feels sturdy yet refined. 

Date of Brand Origin: 2003.
Washes Available: 1.



The 10 Best Men's Bootcut Jeans of 2024: Buying Guide
The 10 Best Men's Bootcut Jeans of 2024: Buying Guide

BEST MINIMALIST BOOTCUT JEANS

Acne Studios 1992 Slim-Fit Bootcut Jeans

Buy Now on Acne Studios: $380

Buy Now on Ssense: $360

When Jonny Johansson cofounded Swedish label Acne Studios in 1996, denim, and specifically raw denim, was at the center of the brand’s identity. That same year, Johansson gave 100 pairs of raw jeans with red stitching to friends and family. Today, jeans are still key, with Acne Studios 1992 jeans offering an ode to ’90s minimalism. The bootcut pants give the perfect slouch at the hem, with washes such as a deep indigo lending an air of confident sophistication to an otherwise informal pant. 

Date of Brand Origin: 1996.
Washes Available: 2.



The 10 Best Men's Bootcut Jeans of 2024: Buying Guide
The 10 Best Men's Bootcut Jeans of 2024: Buying Guide

BEST SLIM BOOTCUT JEANS

Saint Laurent ’70s Flare Jeans

Buy Now on Matches Fashion: $890

Buy Now on Bergdorf Goodman: $990

It’s easy to forget that Saint Laurent was founded with a subversive aim at heart: The eponymous designer sought to blur the line between haute couture and ready-to-wear. Whether by way of Le Smoking or the introduction of slim-cut flared denim for men with the opening of his 1969 Paris menswear boutique, Yves Saint Laurent pushed the boundaries of the French luxury establishment. Today, Anthony Vaccarello has increasingly looked to Yves Saint Laurent’s own ’70s wardrobe for his men’s collections. His Saint Laurent ’70s Flare Jeans, crafted in Japanese denim, may just be the perfect bootcut. In jet black, these refined jeans are easy to dress up or down.

Date of Brand Origin: 1961.
Washes available: 2.



The 10 Best Men's Bootcut Jeans of 2024: Buying Guide
The 10 Best Men's Bootcut Jeans of 2024: Buying Guide

BEST CASUAL BOOTCUT JEANS

John Elliott Caribou Bootcut Jeans

Buy Now on John Elliot:

Buy Now on Neiman Marcus:

John Elliott first caught our eye with his elevated sweats and perfectly cut tees. Since launching his namesake line in 2012, the San Francisco native also zeroed in on the denim game. His Caribou bootcut jeans, available in six washes, take the key properties of the original style and update them with a refined eye. These are jeans you can wear every day that feel thoughtful enough to properly style with, say, a sports coat and oxfords. 
 
Date of Brand Origin: 2012
Washes available: 6.



The 10 Best Men's Bootcut Jeans of 2024: Buying Guide
The 10 Best Men's Bootcut Jeans of 2024: Buying Guide

BEST AVANT-GARDE BOOTCUT JEANS

Diesel 1998 D-Duck Bootcut Jeans

Buy Now on Bloomingdale's: $250

Buy Now on Diesel: $325

Diesel was a major player in the denim renaissance in the early 2000s. Now, the brand is back and stronger than ever with Y/Project’s Glenn Martens at the helm, injecting an undeniable transgressive cool factor. Sometimes, Martens’s goal is simply to shock. (Who can forget the literal mountain of condoms at the brand’s Fall 2023 runway show or the viral impact of a barely there micro mini skirt made from what may be the most mega logo in existence?) In other instances, the designer pushes the sartorial envelope while giving us incredibly wearable products. This is the space Diesel’s bootcut jeans occupy. The brand’s avant-garde aesthetic takes on the denim classic and manages to be both progressive yet pragmatic. 

Date of Brand Origin: 1978.
Washes Available: 1.



The 10 Best Men's Bootcut Jeans of 2024: Buying Guide
The 10 Best Men's Bootcut Jeans of 2024: Buying Guide

BEST UNASSUMING BOOTCUT JEANS

Gap Bootcut Jeans

Buy Now on Gap: $70

The 2000s bootcut era was also a time when malls across America were on its last legs. Inside these behemoth shopping centers, Gap, Abercrombie & Fitch, Hot Topic, and J. Crew reigned supreme (cue food-court nostalgia). While malls may be ghost towns nowadays, many of its staple brands are still with us. Gap, for one, has been here all along, crafting solid bootcut denim. A great example is this staple, which is not too tight, not too pricey, and definitely not pretentious. It’s great for folks looking to step into the water and try something new, looking to try bootcut denim perhaps for the first time. 

Date of Brand Origin: 1969.
Washes Available: 4.



The 10 Best Men's Bootcut Jeans of 2024: Buying Guide
The 10 Best Men's Bootcut Jeans of 2024: Buying Guide

BEST HIGH-FASHION BOOTCUT JEANS

Balenciaga Bootcut Jeans

Buy Now on Matches Fashion: $1,150

Buy Now on Saks Fifth Avenue: $1,150

Buy Now on Balenciaga: $1,150

It was 2016 when Balenciaga, a storied brand in the fashion industry, introduced menswear. The collection, designed by Demna (neé Demna Gvasalia), was cool and sophisticated. It played with proportions (the maison’s signature). It brought a streetwise edge to the runways of Paris, one that many menswear giants soon adopted. Indeed, ever since that inaugural show, Balenciaga has been one of the most directional labels in menswear. It sets the tone for the next few seasons. Prime example: The bootcut jeans that were on full display at the brand’s Spring 2019 show, an era when the masses thought the fit was put out to pasture. And as we can clearly see with this here list, the return of bootcut jeans owes a lot of credit to Demna’s efforts. 

Date of Brand Origin: 1918.
Washes Available: 3.


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