Style | September 16, 2020 10:19 am

The Comfiest Jeans for Guys, 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

This article is part of our Fall Style Guide, a fortnight-long series aimed at helping you figure out how to dress for the coming season, which, as we’ve become accustomed to saying, is going to be quite like any that came before it. At least you’ll look good, though, right?

The first official day of fall is a week from yesterday, but because nothing is sacred and capitalism is, among other things, one big race to be First to Market, fall unofficially started weeks ago. That’s when Starbucks first broke out the big clear-plastic pump bottles labeled “Pumpkin Spice,” your favorite brewery released their worst beer (the pumpkin one) and all the menswear websites turned the page from five-inch inseams and camp collar shirts to cozy flannels, chunky cardigans and moc-toe boots — you know, fall shit.

But while fall is generally a season that’s all about bundling up in comfy, warm clothes meant to insulate you from the increasingly dismal weather, there’s one hallmark of autumnal men’s style that is fetishized for the fact that it is, on first wear, explicitly uncomfortable: denim.

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 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 have anyone to impress this year! More than likely, the vast majority of your jeans-wearing this fall is going to occur in the confines of your own home. So leave the stiff, starchy denims on the rack, and instead embrace the comfy stuff: 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, 12 pairs that fit the bill.

Madewell

Madewell Slim Everyday Flex Jeans in Faded Midnight

A classic faded black 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

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

Duer Performance Denim Slim in Pavement

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 grey, because everyone should wear more grey in 2020. It’s called solidarity.

Outerknown

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

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.

Faherty

Faherty Ocean Wash Denim in Atlantic Wash

Faherty’s brand ethos is basically “don’t leave the beach unless you get hit straight in the face with a meteor,” so it makes sense that their denim would be comfy. The denim in this pair comes from the same mill (North Carolina’s Cone) that made a bunch of menswear activists cry when they ceased operations on their iconic White Oak denim a few years ago (don’t worry, the looms live!). Also, bonus points for the fact that the description on the site starts with the phrase, “No one has time to break in a new pair of denim.”

Levi’s

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

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

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

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

Uniqlo Ezy Jeans

Uniqlo sells $70 jeans for $40, which is already the biggest steal in all of denim-ry, but right now, they’re on sale for $30, so do yourself a favor and steal some.

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.

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