Esquire's guide to buying Levi's jeans
Consider us your sage on this denim-purchasing journey
DENIM IS and always will be the uniform. I already put myself out on the Internet as a Wrangler Cowboy Cut guy. But truthfully, I respect any man’s convictions. If I were at all interested in politics, I’d campaign on some sort of National Jeans Day, Levi’s Day, or something. I would use it to give the country a three-day weekend, instant jump in approval ratings. I’d also make July 20, a holiday—we went to the moon, and that’s worth a three-day weekend.
Anyway, back to pants. My boss wears Buck Mason selvedge jeans. I have a friend that wears vintage Levi’s 501’s. I love them. My wife wears a pair of orange tab Levi’s bell-bottoms I bought for her at a flea market, and they look great. There are my various pairs of Wranglers in various states of disrepair. Point is, there are plenty of ways to wear jeans and plenty of jeans to wear. But to the uninitiated, shopping Levi’s is confusing if you don’t know what all the numbers and sub-labels mean. And as the company has cut more and more corners, more and more fits suck, honestly. But I’m here to be your guide and show you through the entire Levi’s jeans catalog; these are the good ones.
These are the eight jeans most guys will want to land on. The other 12 fits get short mentions at the bottom of the story. I won’t get into deep history, because Levi’s has already done that for me—and I’m guessing you came here to shop and not for a history lesson. Here’s how to shop your next favourite pair.
501 Originals
Levi’s is the house that the 501 built—button fly with a straight (sort of) fit. I’ve already talked about this cut and its new variations at length. But essentially, the fit and materials have changed over the years. The current 501 you pick up on any odd shelf is tapered these days. Now there’s the 501 Original, the 501 Loose, the 501 Relaxed. The most straightforward Levi’s fit is…not that straightforward, nor is it consistent across era. In my opinion, it’s made buying this simple pair of jeans way too complicated—but they ain’t paying me to be the creative director, so I’ll shut-up about it.
If I buy 501s, I like to just hunt for vintage ones. If you keyword search “Made in U.S.A.” on eBay, you will get a pre-2000 501. The ’93 fit (one of my favorites) was the last of the American-made, so that’s likely what you’ll dig up.
For us, we say no stretch in a 501. It’s a classic jean. Wear it the classic way: all cotton. I also prefer the shrink-to-fit version. No need to sit in your tub with them, though. Wash them in a washing machine, put them on wet for a few minutes, then hang dry—you get the perfect fit.
Our Favorite Variations
Levi’s 502
Best Slim Fit Levi’s
A 501 with a zip fly on top and a leg that tapers to a slim hem. If you want a more form-fitting jean without going rockstar-skinny mode, this is a great option. While some guys find the 501 to be a bit basic (it’s not!) the 502 can be a more flattering cut, especially for thinner men.
One thing to note, the 502 will always have a little bit of stretch.
Our Favorite Variations
Levi’s 505
Best 501 Alternative
Besides the 501, the 505 is the classic fit. Levi’s introduced the 505 in 1967 as a modern jean. Today, it’s more of a timeless model. It has a zip fly and just a tad more room than a 501, especially the modern 501. It’s not skater-fit baggy, but if you don’t like how 501’s hug your thighs and taper to the ankle, this is a good fit for you.
Levi’s 510 Skinny
Best Skinny Fit Levi’s
Rockstar skinnies, baby. Will we ever return to peak skinny jeans? Don’t think so. But if it works on your body type, a black skinny jean always has the potential to look good.
Key note is black; skinny jeans work best in black. In indigo washes, they start to look like project-manager pants. Keep them black, keep them cool.
Levi’s 517 Bootcut
Best Bootcut Levi’s Jeans
Throw on some cowboy boots and hit the rodeo, or wear these with some Chuck Taylors and a tight T-shirt for a Dazed and Confused look. Bootcut jeans don’t have the poor fit you remember, and they’re on trend in 2026, so now’s the time to try.
I will say, for what it’s worth, I prefer a Wrangler Cowboy Cut, because it’s a more classic cut. But I have been eyeing Levi’s more fashion-y bootcut—slimmer through the thigh and more flared at the bottom.
Our Favorite Variations
Vintage 517 Orange Tabs on eBay
Levi’s 550 Relaxed
Best Relaxed Fit Levi’s Jeans
Second to the 501, the 550 might have the most ardent following of any Levi’s jean. That’s because it’s the jean of that ’80s and ’90s era. It has that perfectly ’90s laid-back fit.
Thin guys can lean into the baggy look. Bigger guys can rock this fit no problem. These are jeans from the one-size-fits-all era, and they fit us all pretty damn well. If you ask me, this (or maybe the 505) is the be-all, end-all Levi’s cut.
Levi’s 555 Relaxed Fit Jeans
Best Baggy Levi’s Jeans
The 555 (angel number) is where Levi’s does a baggy fit. These can do the skater look, and they can do the Obama dad-jeans throwing-out-a-first-pitch look.
We don’t want to tell you how to live, but this is where we’d tell the average man to stop. If you don’t feel the desire to rock baggy jeans, you shouldn’t be here, and you definitely shouldn’t go to the 568, Levi’s fullest fit.
Every Other Levi’s Jeans Fit Worth Knowing
Those eight are the ones we deem Most Notable, but there are actually about 20 different Levi’s fits right now, in 2026. Here’s a quick rundown of the rest.
511 Slim – Not notable for us, because we say go skinny (510) or a modern tapered 501. This is in the middle, like a 513 with a tapered leg.
514 Straight – Like a 505, except Levi’s gave the jean more stretch. Plus, it has a lower rise, which we think is cool if they fit tight; these don’t. Weird jeans.
527 Slim Bootcut – Fucking love this style. Low-rise, slim in the seat, with a flare—these are Lenny Kravitz jeans. They felt a little too niche to put on the list.
531 Athletic Slim – This one tapers too drastically for us. We like an athletic guy rocking a wider hem.
559 Relaxed Straight – Like the 555, except with a bit more stretch and modern colors.
565 Loose Straight – Big pants! This is a ’90s skate-park fit. No stretch, either!
567 Relaxed Flare – Another trendy one. Looks cool on the right guy, but really requires you to be a ripped surfer wearing flip-flops. If you’re a bigger dude, get one of the other loose fits.
568 Loose – Even baggier and made to sit a little lower. This is as roomy as Levi’s gets.
578 Baggy – If you’re Gen-Z or Gen-A, this is probably your preferred style. Anyone else, except old-head skaters, might want to look elsewhere.
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