13 Flare Jeans and Bootcut Denim Pairs for Men Brave Enough to Channel Kendrick Lamar

If you didn’t catch Kendrick Lamar’s Super Bowl Halftime Show this year, you also missed out on quite the fashion moment.

The 22-time Grammy winner put on a performance (which is now the most watched Super Bowl Halftime Show in history) complete with symbolism, political allusions, and, of course, nods to his ongoing rap beef with Drake. He continued this trend with his choice of clothing. His jacket had the name “Gloria” embossed on the front—a nod to the closing track on his 2024 album GNX, in which Lamar used the name metaphorically. Around his neck was a thick chain that included a lowercase “a” pendant, referencing both his pgLang company and a lyric in “Not Like Us”: “Tryna strike a chord and it's probably A-minorrrrrr.” 

But the most loved garment he wore—by viewer standard, at last—was a pair of flared jeans. After Lamar wore the style during his performance, viewers became internet sleuths and clamored to shop the exact pair. Lamar's Celine flare jeans, that retail for a cool $1,200 quickly sold out and took social media by storm. What better way to signal that flare and bootcut jeans for men are coming back? Plus, Lamar also isn’t the first male celebrity to rock the style recently, as those like Timothée Chalamet and Pharrell Williams have worn it, too. (Flared silhouettes were also prominent in the Pharrell's Louis Vuitton Fall/Winter 2025 collection.)

To shop the bootcut and flare jeans for men look, keep scrolling to shop the top picks to emulate Lamar's look. From a classic pair of Levi’s to a two-toned pair from Diesel, there are options for a range of aesthetics.

For the laid-back, effortlessly look, this pair of Levi’s are a must-have. With a casual fit and relaxed feel through the seat and thigh, they’re perfect for those days when comfort is key but style can’t be compromised. The wide, flared leg adds just the right amount of edge, giving off a confident, retro-inspired vibe.

Levi’s 567 Relaxed Flare Men's Jeans, $98, Levi’s

Crafted from fix denim with a sleek black wash, Diesel’s men's Bootcut jeans are designed for those who want a bold, modern twist on a classic silhouette. The medium waist provides a relaxed fit, while undone seams add extra length, creating a long, lean look that elongates the legs. Stonewashed for a nuanced finish, the front is coated with a black layer that's intentionally cracked, giving these jeans an edgy, tactile feel. Pair them with a graphic tee and leather boots for a rugged, off-duty look, or dress them up with a tailored jacket for a night out.

Diesel Bootcut Jeans, $675, Diesel

With a fit that flatters straight through the hip and thigh before falling into a loose, bootcut leg, Gap's jeans effortlessly balance style and comfort. Their dark rinse gives a polished finish, making them perfect for both casual days and dressed-up evenings. Complete with a zip fly and classic five-pocket styling, this pair proves that timeless design is always in fashion.

Gap Bootcut Jeans, $47 $79.95, Gap

Acne Studios' 1992 jeans are just the pair for a classic fit with a laid-back feel. With their mid-rise waist and subtle bootcut leg, these seamlessly channel a vintage vibe while maintaining a modern look. Crafted from rigid cotton denim, they offer that authentic, structured feel that only gets better with wear. Style them with a graphic tee and sneakers for a nostalgic nod to the ‘90s, or dress them up with a tailored blazer and loafers.

Acne Studios Regular Fit Jeans, $420, Acne Studios

The slim-leg silhouette of these ERL mid-rise flare jeans are simply perfect. With side slit pockets and classic back pockets, they blend functionality with a bold, fashion-forward style. Pair these with a tucked-in shirt and boots for a sleek '70s-inspired look, or go for an edgy vibe with a leather jacket and sneakers. Whether you're dressing up or keeping it casual, these jeans are the perfect blend of retro flair and contemporary sophistication.

ERL Mid-rise Flared Jean, $294 $420, ERL

Designed in a dark wash, these jeans bring a vintage-inspired silhouette into the modern day with a bold flare leg that adds just the right amount of drama. Featuring a zip fly, belt loops, and gold hardware, they blend classic and bold energies. Their whiskering details give a lived-in look, while the single needle stitching and signature horseshoe detailing on the back flap pockets add that True Religion touch.

Joey Flap Flare Jean, $95.40 $159, True Religion

This dark wash pair from AG Jeans offer a timeless fit with a modern edge. These feature a comfortable mid-rise waist and a flattering fit from hip to thigh. A subtle bootcut opening adds just the right amount of flare, making them perfect for pairing with everything from classic loafers to rugged boots. Whether you're dressing up for a night out or keeping it casual, styling possibilities are endless.

Clint Bootcut Jeans, $225, AG Jeans

With a relaxed fit that sits comfortably at your natural waist, the Rhodes Relaxed Boot offers the perfect blend of ease and style. Tapering in at the thigh before flowing into an authentic bootcut leg, these jeans create a flattering silhouette. The Flax wash, a warm, off-white hue, adds a touch of sophistication, complete with pressed front leg creases for a polished finish.

DL1961 Rhodes Relaxed Boot Jeans, $298, DL1961

Crafted from premium Japanese stretch denim, these bootcut jeans offer a soft feel and just the right amount of flexible stretch. The dark blue wash is enhanced with details and sanding for that lived-in look, while the brand's signature seven squiggles embroidery on the back pocket adds an edgy touch. Pair this versatile pair with a tailored blazer and ankle boots for a polished yet laid-back ensemble that works from day to night.

Airweft Brett Bootcut, $248, 7 For All Mankind

Sitting comfortably at the waist with extra room in the hip and thigh, this Silver Jeans pair ensures a relaxed fit that moves with you, no matter where the day takes you. Crafted from performance stretch denim, these offer ultimate flexibility and mobility, making them ideal for those constantly on the go. The dark indigo wash, accented with hand sanding, whisker patterns, and bold contrast stitching, adds a touch of rugged sophistication.

Craig Easy Fit Bootcut Jeans, $94, Silver Jeans

Egonlab's Men's Wide-Leg Jeans redefine modern denim with a bold wide-leg silhouette. Featuring a classic five-pocket design, these jeans blend functionality with statement style. The front button closure and zip fly add a touch of tradition, while the relaxed fit offers contemporary edge. Perfect for those who dare to be different, these jeans prove that casual wear can be just as daring as couture.

Egonlab Wide Leg Jeans, $189 $420, Saks Fifth Avenue

This pair by Citizens of Humanity is a fresh spin on a timeless silhouette, designed with a subtle bootcut leg that effortlessly falls over your favorite footwear. Crafted from heavyweight rigid denim, it offers that coveted authentic feel while channeling a vintage-inspired medium indigo wash. Whether styled with a crisp button-down and pointed-toe boots for a polished look or paired with a relaxed tee and sneakers for an off-duty vibe, this jean is a versatile staple that blends classic appeal with modern ease.

Milo Classic Boot, $278, Citizens of Humanity

Step up your denim game with this pair by Purple Brand, featuring a flared silhouette and faded detailing. The five-pocket finish on these keeps it classic, while the button fly and button closure ensure a comfortable, secure fit. They're perfect for pairing with anything from graphic tees to tailored blazers.

Purple Brand PO72 Super Stack Flare Jeans, $101.25 $225, Saks Fifth Avenue

L'OFFICIEL USA may be compensated and/or receive an affiliate commission if products are purchased through our links.