8 Best Jeans For Older Men To Keep Your Legs Young In 2023

Hello, old guy. Welcome to this article about the best jeans for older men.

Oh? You take umbrage at me calling you an old guy because you’re every bit as stylish as you’ve always been and look way better than you did in your 20s because you make money now and actually care about your body?

Damn right you are, and damn right you do.

Look, my point is that jeans are jeans. And regardless of your age, all that really matters is that they look good and feel good to you. Frankly, you’ve also earned yourself a bit of breathing room in that denim. A little reprieve from the all-that-matters-is-fashion mentality.

With that in mind, here are 8 pairs of jeans for older men that are comfortable, fashionable, and ready to join your closet’s denim ranks.

Key Takeaways 

I’m going to let you in on a little secret. The best jeans for older men are—wait for it—the best jeans. Period. As long as you feel and look great in it, denim doesn’t have an age expiration date. And now that you’re presumably in a position to be picky about what you slap over your legs, don’t skimp on the quality and craftsmanship.

Keep it roomy, comfortable, and classic like my top pick, Corridor’s 5-Pocket Jean. But if your sartorial leanings err more on the old-school side, Lee’s relaxed-fit, straight-leg jeans will always be there for you.

isto.pt / Instagram

Corridor Organic Italian – 5-Pocket Jean – 5-Year Wash

Well, here you are. A man of a certain age who not only appreciates a quality pair of jeans but can actually afford them. And while you’re not the type to shy away from paying a few extra bucks, the craftsmanship and comfort better be there.

Guy, meet Corridor’s 5-Pocket Jean. Corridor 5-Pocket Jean, meet guy. We’re sure you two will hit it off swimmingly.

Washed enough to take on the look of having five years of wear, this 100% organic cotton pair of jeans is milled and sewn in Italy. The combination of their vintage look and regular fit gives them an effortless look suitable for everyday wear. Every day. For years. Seriously, feel free to beat the shit out of these things—they’re not going anywhere.

Material: 100% Cotton | Sizes: 28-38 | Inseam: 28-34.5 | Style: Regular

ISTO Everyday Denim

Oh look, “everyday denim” is right there in the name. Someone needs to give the naming-things guy at ISTO a raise because he really nailed it this time. Designed to be worn forever and always, these beauties are made from exceptional denim by a popular supplier in Italy, then cut and sewn in Portugal.

Which is all good and fine. But turns out, they’re also super comfortable, look great, and will serve you for decades if you take care of them. ISTO’s Everyday Denim jeans also come in off-white and washed black, but stick with blue to get the most mileage out of them.

Material: 76% Organic Cotton, 24% Recycled Cotton | Sizes: 28-38 | Inseam: 30-32 | Style: Relaxed

Closed Unity Slim Jeans

Considering the fact this article is about the best jeans for older men, file this one in the “If You Must” category. Sure, plenty of older guys can pull off skinny jeans like they could back in the day, but it’s a pro move best executed by aging rock stars and silver fox influencers. Which is part of the reason why I’m including a slim option instead of a true skinny option.

The main difference between slim and skinny jeans is that the former typically has a wider leg opening. And it’s the wider leg opening of these Unity Slim Jeans from Closed that makes all the difference in terms of universal wearability. Made in Italy, it’s a sturdy pair of jeans that has a light stretch and comes in a classic faded blue.

Material: 98% Cotton, 2% Elastane | Sizes: 27-38 | Inseam: 32-34 | Style: Slim

Represent Baggy Denim

I see you, edgy rocker dad with a former rebellious streak. So does Represent and their Baggy Denim jeans that come in an immaculate jet-black that’s all but begging to become an everyday wear for the color-averse.

The baggy cut is a good choice for older men looking to prioritize comfort, but not at the expense of style. The buttons are embossed with Represent’s logo and there’s a metal D-ring attached to one of the front belt loops. Rest easy, friend, for your metal D-ring search is at long last over.

Material: 98% Cotton, 2% Elastane | Sizes: 28-38 | Inseam: 32.1 | Style: Baggy 

Lee Men’s Premium Select Relaxed-Fit Straight-Leg Jean

It doesn’t get much more gloriously old-school than Lee jeans. The Kansas-born company has been around since 1889 for a reason. Their sturdy, reliable, comfortable, versatile jeans will age as gracefully as you, and it doesn’t hurt that they also happen to be super budget-friendly.

The classic, relaxed fit of these jeans is perfect for pedestrian pursuits like walking the dog and making four-too-many Home Depot runs. But that versatile side kicks in when you pair them with a jacket or a button-down for a casual night out.

Material: 100% Cotton | Sizes: 29-42 | Inseam: 30-34 | Style: Relaxed

Levi’s 501 Original Fit Jeans

What more can be said about Levi’s 501s that hasn’t already been said? Not much. But I guess I could still mention that they have nearly 60,000 5-star reviews on Amazon. And that they’ve been alive and kicking since 1873, which is a… pretty good track record.

But you knew all that. In fact, you probably already have a pair of these straight-leg, regular-fit beauties in your closet. If so, keep up the good work and consider this validation of your denim decisions. If not, you’re on notice. Just kidding. Kind of. I’m not kidding.

Material: 100% Cotton | Sizes: 28-44 | Inseam: 30-32 | Style: Regular

Raleigh Workshop Alexander: Selvage Raw

By their very workhorse, go-anywhere, do-anything nature, it’s hard to label any pair of jeans a “luxury” product. That’s especially true when it comes to the American grit and personalized love that goes into a pair of selvedge denim jeans from Raleigh Workshop. But alas, they ain’t cheap. And they’re sure to become a prized pair among your collection.

The Alexander is full of personalized, special features like a hand-stamped leather patch in the back and the actual signature of the person who made your jeans on the inside of the front pocket. Elsewhere, you’ve got antique brass rivets and buttons, subtly handsome red stitching throughout, and a unique paintbrush stroke detail across the back-right pocket.

Material: 100% Cotton | Sizes: 28-40 | Inseam: Bespoke | Style: Relaxed

Rye 51 4-Way Stretch Jean – Ellis Wash

Speaking of stretchy denim, a lot of older guys consider that feature a must when it comes to overall comfort and an acceptable range of motion. Rye 51 uses a soft, 4-way stretch denim designed to move with you throughout the day.

Pick up a pair of the damn-near-white Ellis Wash colorway, toss on your favorite pair of New Balance, and embrace the dad-clothes movement from the inside looking out. But lest you slip too far into Instagram dad-meme territory, Rye 51 employs a slim, straight-leg fit to keep you looking your modern best.

Material: 100% Cotton | Sizes: 30-40 | Inseam: 33.5-34.5 | Style: Slim  

man in a stripped shirt holding a plastic cup
closedofficial / Instagram

What To Look For In The Best Jeans For Older Men

Size & Fit

I’ve said it before, and I’ll say it again: You’ve earned a little breathing room in your denim. If you’re a slim guy, you might be able to pull off a pair of skinny jeans just as well as you did back in the day. But if you’re a man of leisure and prioritize comfort over all else, there’s no shortage of relaxed, loose-fitting jeans for older men out there. To find the pair that best suits your lifestyle, pay close attention to the fit and size options.


Skinny. Relaxed. Tapered. Loose. Flannel-lined. The list of denim styles goes on and on. The style you choose goes hand-in-hand with the size and fit in that it’s just got to work for your body and lifestyle. Hate to burst your bubble if you fit this description, but not every older guy can pull off skinny, black, ripped jeans. Just be yourself and let the style chips fall where they may.


In the pantheon of jeans for men of a certain age, color has—for whatever reason—been a polarizing topic. “Dad jeans” have gotten a bad rap for being too big and too light-washed. But if that’s your look, you do you. Just know that you don’t live in a box, and neither do your denim colorways. From everyday dark indigo to stark white, you’ve got options.

man doing the Egyptian pose
raleighworkshop / Instagram

Final Verdict 

The best jeans for older men are the ones that look and feel great on you, be they Japanese denim or run-of-the-mill basics. Don’t try getting away with a look your body can’t support, and don’t force anything. Stick with those loose guidelines, and the denim world is your oyster. Corridor’s 5-Pocket Jean is a great place to start, but you’re spoiled for choice otherwise.


    • Not only should older men wear jeans, everyone should wear jeans. Denim is one of the most comfortable and versatile wardrobe essentials that can be worn by every person of every age—and for almost every occasion.

      • When it comes to sizing your jeans, let your body type be your guide. Measure your current waist size (not your ideal waist size) and take things from there. Don’t try squeezing into a pair of jeans that just isn’t going to work for you. Instead, keep things stylish but cozy.

        • If you’re over 50—or any age, for that matter—you should wear… well, whatever the hell you want. If you can confidently pull off a pair of the best jeans for older men without looking like you’re trying too hard, then congratulations. You did it. There’s nothing you “should” or “shouldn’t” wear as long as it looks and feels good.

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