The Types of Jeans Every Man Should Own

We’ve really strayed on the denim front. People, even us at Esquire, try to prescribe boundaries and trends to jeans. Skinny jeans are over, don’t wear them. Flares have died, revived, died again, and wait actually now they’re back. It’s all too much. This isn’t what jeans are about.

Jeans, more than any other garment, should be a personal style building block. They should be timeless. You should buy them new, wear them until they fit like a glove, and then never take them off. The specifics matter way less than making them yours. That’s what’s so cool about denim. For example, my denim hero is Serge Gainsbourg. He’s kind of strangle looking, but when you see him in old pictures with double denim underneath a suit jacket, he looks so fucking cool. That’s what well-worn denim can do for you.

We’ve already given you a discovery guide to denim, so this is going to work a little bit differently. I’m just going to tell you what models I think are worth your money. To do that, I’ll use my own fashion categorizing system: Everyday, Elevated, and Esoteric. Everyday is easy to understand; you want some marriage of comfort, durability, and look. Elevated means you really care about your look. Esoteric means you want a story to go along with your jeans; you care about how it’s made and by whom. Choose your path accordingly and dive in.

Everyday

Buck Mason

Buck Mason does a hard-wearing everyday jean to perfection with its Full Saddle in selvedge denim.

Let’s start with the simplest category. Personally, this is where I think jeans should fall. Jeans are a holdover workwear garment, and they want to be treated as such. When they’re made with a denim that has any sort of heft (anything over 13oz.), they really need to be worn hard for breaking in. The main focus here is not just the look; that’s the Elevated Jean. The main focus isn’t the fabric, loom they were made on, or traditional dying technique; that’s the Esoteric Jean. Here, we’re looking at easy to buy, easy to wear, and durable.

For my money, the jean that does that is the raw denim Wrangler Cowboy Cut for $40. I’m dead serious. If you buy what Wrangler calls, “Rigid Indigo,” that’s a pair of 14.75 oz. raw denim jeans. There’s no other brand that makes jeans like this at this scale. I wear mine to death, and it still takes a year before they look anything close to worn in. They’re cut well, with a fitted seat and high back pockets that make you look good. These are bootcut jeans, but the flare is subtle, bordering on imperceptible. They work with cowboy boots and ropers, but they wouldn’t look crazy over work boots. Wearing them with regular shoes takes some know-how. With a leather loafer or vintage sneaker, go to the extremes of break; you want no break or a full break that might even be pooling. That said, never wear them with a modern sneaker, even a nice dress one. It’ll look a bit off.

So what are the alternatives to my John Wayne jeans? First, I’ll say Levi’s Original Shrink to Fit. These are the only new jeans I’d buy from Levi’s, because it’s the only pair that’s got a somewhat original cut and stretch-free, raw denim. That said, they’re pretty thin jeans, markedly less durable than the rest of this list.

Beyond Levi’s, there are a few other big retailers that make nice jeans, but there’s a price jump to around $200, where you start getting high-quality Made in U.S.A. options. Buck Mason is one. The Full Saddle jean in selvedge is what I’d give most guys, and our Editor-in-Chief feels the same. They’re a classic cut, made in America jean for $250, which is a decent value. If Buck Mason feels too Americana, Ayr is an essentials brand that actually cares about quality. Its Normie Jean jean is perfect for a regular, “I just want to look good,” type of guy. And though 3Sixteen was once part of the esoteric denim guy world, it’s so widely stocked and well-priced now I’d recommend it to regular raw denim-curious men. I’d start with the CS-100x, a classic fit, hard-wearing, raw denim jean that’s on the cusp of becoming Esoteric. Or buy the RS-100x for a more relaxed cut.

Elevated

husbands paris

Husbands makes a trouser-like jean, with a high-rise and straight leg, that elevates the form.

This is where cut and looking good are the main focus. These are the jeans you can sneak into nice dinners with. Even in the year 2025, I think slim—or I should say fitted to encompass straight cuts?—is the way to go here. It just looks more put-together.

My favorite jeans in this category are from Husbands, a Parisian brand with a nonchalant take on tailoring. Its High-Waisted Jeans are my Platonic ideal of jeans, though more of a classic trouser silhouette done in raw denim. I tried them on at the store in Paris, and they were just phenomenal. The cut gives you some visual height and the jeans were fitted in a really flattering way. Plus, I think a high rise flatters just about every body type.

I can also talk slim and tapered, since that’s where most guys still fall. These get maligned in fashion circles, but I think when done right it’s great for guys who aren’t obsessed with fashion but want to look good. There are two keys though: avoid stretch and avoid going too skinny. Stretch is just a bad shortcut. Too skinny can look cool—I still believe that—but you have to lean into the skinny jean thing. So for classic #menswear, I’m a Georgia boy and I’ll still ride with the Slim Straight from Sid Mashburn, a less constricting version of the A.P.C. New Standard made of high-quality 15 oz. selvedge denim. Keeping it down South, Raleigh Denim out of Raleigh, North Carolina, makes great small-batch jeans as well. The Jones fit is a nice slim straight cut. If a slim seat and thigh isn’t your thing, go for a respectable taper. I’d go back to Buck Mason for the Ford Standard Fit. Drake’s also makes a nice tapered jean that looks great with an oxford and a blazer.

And if your concept of Elevated leans more “capital F” Fashion, I’d say tread lightly. Pick based on cut. I’d follow Hedi Slimane wherever he goes after Celine because I think rockstar skinny and flares are cool. The current Celine selection is where you can currently shop his wares. Rick Owens is another designer who does denim well, and his avant-garde approach is toned down in the jeans section. RRL, the Westernwear line of Ralph Lauren, also has a great selection of jeans, mostly based on classic models. Our Legacy is another shoutout for fashion-forward cuts.

Esoteric

Self Edge

It doesn’t get more, “Can I tell you about my jeans,” than Sugar Cane’s 1966—based on the old Levi’s 501 cut, woven with cotton and sugarcane fibers.

This is where the world of jeans starts to infinitely expand into a nerdy subculture. It’s huge in the U.S. but most of the brands reproducing high-quality Americana are actually over in Japan. You’ll probably know Kapital, but there are smaller companies doing similar things. I’m not going to bore you with all the stories, because it’s just too much. If you’re interested, start with the brands stocked at specialist denim retailer Self Edge and expand from there into stuff you can’t find stateside.

For some callouts, Sugar Cane is cool, specifically the 1966 and 1947 models that are based on Levi’s 501s from those respective years. Samurai, based out of Osaka, makes great jeans, one of which is a pair cut from 25 oz. denim, probably the heaviest you’ll find. Freewheelers is another well-known one; ditto Iron Heart. Pure Blue Japan (PBJ) is another well known brand. I’ll stop here, but this is like .001 percent of what you can get into.

That about covers all your bases. It at least gets you started in one of three directions for buying denim. At the end of the day, remember this: your jeans should be the least interesting thing about you. If you meet another dude with cool jeans, tell him, but don’t expect people will come up and compliment your fades or fit or whatever. No one really cares. Wear what you think is cool.