Style | Updated September 13, 2022 10:19 am

The Most Comfortable Jeans for Men

Pants season is upon us. Ease into it.

a collage of denim on a mulit-colored background
Fall requires jeans. Choose the most comfortable option.
Getty Images

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For more than a decade, menswear heads have been obsessing over the weight and “rawness” of their jeans, which basically means that rather than coming off the rack feeling, uh, wearable, they’re more akin to the Tin Man’s pants, and it is up to you to spend the next four weeks breaking them in. We’re not talking about those. While dark, crisp raw denim looks really good —pairs with pretty much anything in your closet, from a plain white T and some knock-around boots to a blazer and your best pair of brogues — they’re also far too advanced for the early days of fall. We’re talking about the most comfortable jeans you can find.

Think of comfortable jeans as an extension of your summertime wardrobe: washed, worn-in denim in roomier cuts and flexible fabric blends aren’t that far of a cry from corduroy shorts and 5″ inseams. The best part? These jeans (at least the ones we’ve highlighted) will actually look as good at happy hour, too. They’ve got watching football, drinking Octoberfests and carving pumpkins on lock. They feel like your sweats, and look like a million bucks. Below are 15 of the most comfortable jeans that fit the bill.

a pair of light wash slim jeans on a model
Madewell Slim Everyday Flex Jeans
Madewell

Madewell Slim Everyday Flex Jeans

A classic light-wash jean in a timeless slim cut for guys who aren’t quite ready to go full Jerry Seinfeld. Don’t worry: thanks to a blend that includes 2% elastane, they’re super flexible and movement-friendly all the same.

a pair of medium wash jeans on a model
Gap Slim GapFlex Jeans
GAP

Gap Slim Jeans in GapFlex with “Washwell”

We’re not entirely sure what “GapFlex” is, but it has the root flex in it, and the material includes lycra and a generous helping of polyester, so we’re gonna guess it’s alluding to the fact that these jeans are very, very pliable (that’s going to be a theme on this list). Plus, you can feely (slightly) better about copping a pair, since Gap’s Washwell program means less water and less waste went into make this denim.

a front/back shot of a pair of black jeans on a model
Duer Relaxed Performance Denim
Duer

Duer Relaxed Performance Denim

Duer is a company that specializes in “performance” denim for “doers,” which basically means people who are doing things that you wouldn’t normally do in jeans, like riding a bike or wearing them in summer (their “weightless” summer denim is truly a godsend). This pair is extra stretchy, but relaxed and laid-back — exactly how we want our pants to fit in 2022.

a pair of dark blue jeans from Ralph Lauren on a grey background
Ralph Lauren Purple Label Selvedge Jean
Ralph Lauren

Ralph Lauren Purple Label Slim Strech Selvedge Jean

Who said comfortable jeans should be cheap? Ralph Lauren’s Purple Label denim are positively worldly, made in Italy from Japanese stretch denim developed using traditional weaving techniques and dyed a deep indigo hue. All of that to say, this would be our absolute recommendation for anyone who has $800 to spend on denim.

a pair of large light wash jeans
Outerknown Statesman Relaxed Selvedge Jean
Outerknown

Outerknown Statesman Relaxed Fit Selvedge Jeans

You know Outerknown: Kelly Slater, sustainability, expensive, etc. I usually only shop them during their huge warehouse sales, but I’ll make an exception for their S.E.A. denim, because it’s guaranteed FOR LIFE. These ones are cut from a 13.5-oz. Italian cotton selvedge denim, and between their ultra-roomy fit and worn-in feel, they’re the only pants I wanna toss on.

two model shots of a model in a pair of J.Crew japanese denim
J.Crew 770 Stretch Selvedge Japanese Jean
J.Crew

J.Crew 770 Straight-Fit Stretch Indigo Raw Selvedge Japanese Denim Jean

Japan has replaced America as the world’s most sought-after denim fabricators because they can afford to care about things like quality and craftsmanship, rather than simply cranking out as many sheets of fabric as is robotically possible each day. These ones are in J.Crew’s “straight” fit, which is roomy in the seat and straight through the legs.

a pair of slight medium blue denim jeans
Flint and Tinder All-American Straight Stretch Denim
Huckberry

Flint and Tinder All-American Straight Stretch Denim

Despite being cut from a sturdy and durable American-made fabric, Flint and Tinder’s Selvage Jeans still manage to offer comfort by way of built-in-stretch that helps to support one’s body movements, meaning you can wear them all day long sans any discomfort. We’re partial to this wash for it’s signature antique metal buttons, chain-stitched hem and distressed coloring.

a dark, loose jean on a model
Levi’s 541 Athletic Taper Flex Jeans
Levi’s

Levi’s 541 Athletic Taper Flex Men’s Jeans

If you’re a Levi’s guy, you probably already know which “number” you prefer, but if that number is 501 or 511, maybe let loose and try something with a little more breathing room this year? It’s just an idea. A very comfy, flexible idea.

a pair of black corduroys on a model
Buck Mason Strech Cord Ford Standard Jean
Buck Mason

Buck Mason Stretch Cord Ford Standard Jean

If you’re not a “jeans guy,” Buck Mason’s Cord Ford is the perfect middle ground between a word-appropriate chino and a snappy spandex-infused jean. It’s not even really a jean, as it’s constructed with a 1% elastic — for the give, of course — 14-wale stretch cord. But they’re so comfy that we’ll let it slide.

a pair of flannel lined jeans on a model
L.L. Bean Beanflex Fleece-Lined Jeans
L.L. Bean

L.L. Bean Standard Fit BeanFlex Fleece-Lined Jeans

Fleece-lined and stretch might feel to to opposite ends of the denim spectrum, but L.L. Bean’s patented BeanFlex® makes it work. Flannel-lined jeans are perfect for those (quickly approaching) freezing days where both warmth and comfort is a necessity, especially if you can actually walk in them

a pair of big white denim jeans from Stussy on a grey background
Stüssy Overdyed Big Ol Jean
Stussy

Stüssy Overdyed Big Ol Jean

For most all of the jeans on this list, their comfort is derived from a stretch blend or premium fabric, but for Stüssy’s denim option, it comes down to sheer size. The Big Ol Jean lives up to its namesake with a surplus of roomy, 100% imported cotton and a massively relaxed cut leg.

a pair of black organic denim jeans
Everlane The Slim 4-Way Stretch Organic Jean
Everlane

Everlane The Slim 4-Way Stretch Organic Jean

Every man needs at least one pair of black jeans — no one will notice if you wear them two days in a row, and more importantly, they go with everything. Seriously, everything. You may think your blue jeans do that, but spend a week mixing and matching your wardrobe with a pair of black jeans, and you may never return.

a pair of medium dark jeans on a walking model
Uniqlo Ezy Ultra Stretch Jeans
Uniqlo

Uniqlo Ezy Ultra Stretch Jeans

While they’re not on sale right now, chances are they will be in the future, so you’d be wise to keep an eye on Uniqlo’s Ezy Ultra Strech Jeans. But hey — we’re not that mad about the $50 price tag either. Especially when you could run a damn marathon in these things.

a pair of high-end medium blue jeans
Acne Studio Slim-Fit Tapered Stretch-Denim Jean
Mr. Porter

Acne Studios Slim-Fit Tapered Stretch-Denim Jeans

A really cool pair of jeans that absolutely nail the ’90s-throwback formula that has been de rigueur for the last few seasons. It’s the details that make them: conspicuous white stitching, medium rise and a larger-than-normal cuff opening (but not so much as to veer into bootcut territory, which can be a stretch if you don’t commit). If you’ve been thinking about trying your hand at the whole normcore thing but aren’t sure where to start, this is a good entry point.

two model shots of a model in Todd Snyder denim
Todd Snyder Straight Fit Stretch Jean
Todd Snyder

Todd Snyder Straight Fit Stretch Jean

The Straight Fit Strech Jean is an excellent middle-of-the-road option for the guy who just wants a pair of regular, comfortable jeans; not too expensive but crafted with impeccable quality.