16 Most Comfortable Jeans for Men
Wearing denim doesn't have to suck — here's the proof
Nota bene: If you buy through the links in this article, we may earn a small share of the profits.
Nothing is truly binary, but if you want to get as mathematically close as possible to a true 1’s and 0’s situation, try asking a fella about his jeans preference. Unlike the plethora of ways dress up, wear sweaters or just generally exist in the universe, jeans (and the guys who wear them) fall into two distinct camps — stiff, influencer-coveted selvedge denim and their antithesis…cozy, comfortable jeans.
While menswear heads have been obsessing over the weight and “rawness” of their jeans — this 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 here to talk about those. Yes, that dark, crisp, raw denim looks really good, and 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, but at what cost? No, jeans with a touch of stretch, those made from a pre-washed cotton weave or just joints generally constructed not to break your thighs and your soul are what we’re currently after.
Think of these comfortable jeans as an extension of your sweatpants collection: washed, worn-in denim in roomier cuts and flexible fabric blends aren’t that far of a cry from fleece joggers and cozy knits. 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 the Super Bowl, drinking Sam Adams and seeing out winter on lock. They feel like your sweats, and look like a million bucks. Below, 16 of the most comfortable jeans that fit the bill.
The Best Comfortable Jeans for Men in 2023:
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.
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 feel (slightly) better about copping a pair, since Gap’s Washwell program means less water and less waste went into making this denim.
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.
Ralph Lauren Purple Label Slim Strech Selvedge Jean
Who said comfortable jeans should be cheap? Ralph Lauren’s Purple Label denim is 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 $500 to spend on denim.
A surefire way to guarantee comfy jeans? Get an absolutely massive pair, like Abercrombie’s Loose Workwear Jean. Featuring a cut that’d make the gnarliest of skaters green with envy, they’re cozy in a big way.
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. And oh, look at that — these bad boys are on sale, after all.
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.
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.
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.
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.
L.L. Bean Standard Fit BeanFlex Fleece-Lined Jeans
Fleece-lined and stretch might feel like 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 are a necessity, especially if you can actually walk in them
Corridor Organic Italian 5 Pocket Denim Jeans
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 quality. Milled, sewn and washed in Italy by Candiani, these vintage-inspired joints are hand-sanded and washed for an immediate lived-in feel. We haven’t taken them off since we copped.
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.
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.
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.
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.
We've put in the work researching, reviewing and rounding up all the shirts, jackets, shoes and accessories you'll need this season, whether it's for yourself or for gifting purposes. Sign up here for weekly style inspo direct to your inbox.
Deals of the Day
InsideHook may earn a share of the profits.
Note that deals are subject to change at any time.
Suggested for you