The Most Comfortable Jeans for Men, Because Wearing Pants Shouldn’t Suck

Wearing denim doesn't have to suck — here's the proof

Updated September 28, 2023 10:19 am
a collage of comfortable men's jeans on a denim background
Life requires jeans. Choose the most comfortable option.
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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 man about his jeans preference. Unlike the variety of ways to get dressed up, wear shirt jackets and just generally exist in the universe, jeans (and the guys who wear them) fall into two distinct camps — the brutalists of stiff, influencer-coveted selvedge denim and their antithesis… fellas who search for the most comfortable jeans they can find.

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What Makes a Jean “Comfortable”?

While menswear heads have been obsessing over the weight and “rawness” of their jeans — this means that rather than coming off the rack feeling, uh, wearable, they’re more akin to concrete pants, and it is up to you to spend the next four weeks breaking them in — along with how to store them, 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, 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.

Comfortable jeans should basically function 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 your favorite mustard-stained pajama pants. To that end, most all will include a touch of elastane or similar poly-blend for that added stretch, and many have been brushed to avoid any scratchy, rough denim.

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With fall all but here and pants in high demand, even the wide world of chinos can’t cover all your bases, so bite the bullet and keep scrolling. After all, we’ve (post-researching, testing and compiling) identified a variety of jeans that feel like leg heaven and don’t look half bad, either. They’ve got watching the Redzone and crushing Sam Adams Octoberfest with the broskis (read: your toddler’s friends dads) on lock. They feel like your sweats, and look like a million bucks. Below, the most comfortable jeans a man can wear.

The Most Comfortable Jeans for Men in 2023:

A classic dark 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.

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.

Who said comfortable jeans have to be cheap? Ralph Lauren’s Vintage Jeans, made from indigo-dyed cotton stretch denim stretch, is an OG silhouette that sits high on the waist. All of that to say, this would be our recommendation for anyone who has exactly $150 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.

You know Outerknown: Kelly Slater, sustainability, expensive, etc. But their denim is serious stuff, too…in that it’s seriously comfortable. Blame it on the slightly higher rise than you’re used too and a mid-weight 12 oz organic cotton. There’s some stretch in there too — maybe even enough to surf in.

We’ve been chronicling J.Crew’s rebirth as a serious player in menswear for what feels like an eternity now, and if their updated “classic” jeans are any indication, they’re here to stay. Straight through the hip, leg and ankle, they’re just the pair to toss on with a vintage L.L. Bean flannel and a pair of don’t-care-but-actually-care-too-much work boots.

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 its signature antique metal buttons, chain-stitched hem and distressed coloring.

The Relaxed Fit Jean from Todd Snyder is an excellent middle-of-the-road option for the guy who wants a pair of regular, comfortable jeans that he can where everywhere; not too expensive but crafted with impeccable quality. Yes, they’re technically a selvedge pair, but the 12.5-ounce, 100% cotton weave breaks in in no time at all and feels like you’ve owned them for years.

A touch of elastane is commonplace in denim nowadays, but four-way stretch? Everlane is built diffrent, bro. The organic denim is organically farmed and milled in Turkey, cut relaxed and looks fairly James Dean-esque for being an indigo blue pair of athleisure joints.

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.

If you’re not a “comfortable jeans: guy but are playing with the idea, Buck Mason’s Full Saddle Jenas are the perfect middle ground between a crispy Japanese Selvedge pair and a relaxed spandex-infused jean.

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