Style | Updated January 3, 2021 8:13 pm
Originally Published September 16, 2020 10:19 am

The Most Comfortable Jeans for Men, Since That’s the Only Qualifier That Matters Right Now

Raw denim has its merits, but in 2020, you want something soft, cozy and livable

Comfiest denim

Nota bene: If you buy through the links in this article, InsideHook may earn a small share of the profits.

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. What follows is an excruciating process that will literally leave dye all over your socks and shoes (don’t wear white sneakers!) as well as pinch, poke and scratch the hell out of your inner calves and thighs, but it will all be worth it at the end, because you’ll have a pair of comfortable jeans that have developed all sorts of cool creasing and distressing while uniquely conforming to your exact body type.

And it works, more or less. Dark, crisp raw denim looks really good, and thanks to its starkness and simplicity, you can pair it with pretty much anything in your closet, from a plain white T and some knockaround boots to a blazer and your best pair of brogues.

But guess what: You don’t always have to impress someone. Especially if they’re only seeing you chest up on a Zoom call. So leave the stiff, starchy denim on the rack, and instead embrace comfortable jeans: washed, worn-in denims in roomier cuts and flexible fabric blends.

Will they look as good at happy hour? Probably not. But they’re better for watching football, chopping wood, raking leaves and drinking beer, and that’s what you need right now. Below are 12 pairs of comfortable jeans that fit the bill.

Slim Everyday Flex Jeans in Gramling Wash

Madewell Slim Everyday Flex Jeans in Gramling Wash

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 Soft Wear Slim Jeans with GapFlex

Gap Soft Wear Slim Jeans with GapFlex

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). Slightly wider through the leg than the Madewells above, but still a tailored fit.

Duer Performance Slim Denim

Duer Performance Denim Slim in Antique Black

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, slim and greyish-black because everyone should wear more grey in 2021. It’s called solidarity.

Outerknown Ambassador Slim Fit: Selvedge

Outerknown Ambassador Slim Fit: Selvedge

You know Outerknown: Kelly Slater, sustainability, too 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 they’ve got some really nice fading and distressing without going full “What, did you get in a fight with the lawnmower?” (Don’t worry, you’ll find a pair of those below.)

J.Crew 1040 Athletic-Fit Stretch Jean in Resin Rinse Japanese Denim

J.Crew 1040 Athletic-Fit Stretch Jean in Resin Rinse Japanese Denim

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 new-ish “athletic” fit, which is roomy in the seat but still has a decent taper at the ankles. Remember: dad jeans are back, but bootcut jeans are absolutely still lame as fuck.

Flint and Tinder Stretch Selvage Denim 13.4oz

Flint and Tinder Stretch Selvage Denim 13.4oz

Despite being cut from a sturdy and durable 13.4oz fabric, Flint and Tinder’s Selvage Jeans still manages 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 vintage-inspired wash featuring patina accents along the front of the leg for that perfectly worn in look.

Levi's 541™ Athletic Taper Men's Jeans

Levi’s 541™ Athletic Taper 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 idea.

Bonobos Men's Premium Stretch Jeans

Bonobos Men’s Premium Stretch Jeans

A slightly more restrained pair of jeans for casual Fridays at the office you’ll have to go back to sooner or later. And in the meantime, these are yet another pair with some sneaky flexibility built in, this time thanks to a 1% elastane and 5% polyester blend.

Joe's Jeans The Rhys
Joe’s Jeans

Joe’s Jeans The Rhys

What, did you get in a fight with a lawnmower? Despite the holes on display here, Joe’s makes a very good pair of pants, and this light-wash, heavily distressed number makes for a nice complement to the darker, more traditional denims that populate most of this list, and probably your closet as well.

Everlane The Slim 4-Way Stretch Organic Jean

Everlane The Slim 4-Way Stretch Organic Jean

Every man needs at least one pair of black jeans, because 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 Jeans

Uniqlo Ezy Jeans

While they’re not on sale now, chances are they will be in the future, so you’d be wise to keep an eye on Uniqlo’s Ezy Jeans. But hey — we’re not that mad about the $50 price tag either.

Acne Studios Slim-Fit Tapered Stretch-Denim Jeans
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 again, is terrible). 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.