Let's be real. If you told anyone five years ago that we’d be unironically wearing long jeans shorts for men again—the kind that swallow your kneecaps—they would have laughed you out of the room. We spent a decade in the "slim-fit" trenches. Everything was tailored. Everything was short. If your shorts didn't hit three inches above the knee, you were basically wearing capris, right?
Wrong.
Fashion is weird. It’s cyclical, sure, but the return of the long denim short (or "jort," if you’re into the lingo) feels different because it’s a direct rebellion against the restrictive clothing of the 2010s. You’ve probably seen them on your TikTok feed or on guys catching a flight at LAX. They’re heavy. They’re wide. They look like something your dad wore to a backyard BBQ in 1996, but somehow, they’re the coolest thing in a guy's wardrobe right now.
The Adam Sandler Effect and the shift in silhouette
You can't talk about long jeans shorts for men without mentioning the "Adam Sandler-core" phenomenon. Sandler has been the king of the baggy jort for thirty years, mostly because he seemingly does not care about what anyone thinks of his inseam. But lately, high-fashion brands like Balenciaga and streetwear giants like Stüssy have leaned into this exact "shlumpy" aesthetic.
It’s about volume.
When you wear a pair of shorts that hit below the knee, you change the entire geometry of your outfit. It’s not just a "short" anymore; it’s a structural piece. Most guys are gravitating toward a 10-inch to 12-inch inseam. This isn't just a comfort thing. It’s a vibe. You’re trading the "I just came from the golf course" look for something that feels more grounded in skate culture and 90s hip-hop. Honestly, it’s a relief. You can actually sit down without feeling like your circulation is being cut off by a tight leg opening.
Why the "skater" jort is winning
If you look at brands like Levi’s or Carhartt, their sales reflect this shift. The Levi’s 568 Stay Loose shorts are flying off shelves. Why? Because they mimic the vintage 501s that people used to DIY at home by hacking off the legs of old thrift store finds.
There is a specific weight to these shorts that you don't get with chinos. We’re talking 12oz to 14oz denim. It’s rugged. It holds its shape. When a pair of long jeans shorts for men has that much fabric, it drapes differently. It doesn't cling. It creates a straight line from the hip to the mid-calf, which, surprisingly, makes a lot of guys look taller because it simplifies the silhouette.
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Think about the SilverTab era. That’s what we’re reliving. But instead of the neon windbreakers, we’re pairing them with oversized hoodies or cropped white tees to balance the proportions.
The raw edge vs. the finished hem
Here is where guys usually mess up.
A finished hem—the kind that’s folded over and stitched—looks "cleaner." It’s more "I’m going to a nice lunch." But the raw hem? The one where the threads are hanging off and it looks like you used a pair of kitchen scissors? That’s where the character is.
If you’re going for a vintage look, the raw edge is non-negotiable. As you wash them, the denim frays. It builds a "fringe" that adds texture to the bottom of the short. It breaks up the harsh line across your shins. If you buy a pair with a finished hem and they feel too stiff, just cut the bottom inch off. Seriously. It transforms the garment.
Solving the "clown" problem: How to style long denim
The biggest fear guys have with long jeans shorts for men is looking like a kid in their older brother’s hand-me-downs. It’s a valid concern. If you wear baggy shorts with a baggy shirt and flat shoes, you look like a rectangle.
The Shoe Choice: This is the make-or-break moment. You cannot wear "slim" shoes with long denim. If you put on a pair of low-profile loafers or thin canvas sneakers, your feet will look like toothpicks sticking out of two denim pillars. You need bulk. Think New Balance 990s, ASICS, or chunky loafers with a lug sole. You need a shoe that has enough visual weight to "catch" the bottom of the short.
Socks Matter: No-show socks are dead here. You want a mid-calf white crew sock. Brands like Bombas or even the classic Gold Toe. The goal is to fill the gap between the bottom of the short and the top of the shoe. This creates a continuous line of color and texture.
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Top Proportions: If the shorts are wide, your shirt needs to be either equally wide or slightly cropped. A long, skinny t-shirt is the enemy of the long denim short. It creates a weird, sagging midsection. Try tucking in your shirt. It sounds old-school, but a tucked-in white tee with a belt and long jorts is a classic 1950s workwear look that still hits today.
Reality check: The weight and the heat
Let’s be honest about one thing: long jeans shorts for men can be hot.
If you live in a place where it’s 100 degrees with 90% humidity, wearing twelve ounces of raw indigo denim down to your shins might feel like a mistake. Denim doesn’t breathe like linen. It’s cotton, but it’s dense.
However, the "long" part of the short actually provides some sun protection, and because the leg opening is usually wider (often 11 to 13 inches across), you get a chimney effect. Air moves up through the bottom. It’s often cooler than wearing slim-fit chinos that are glued to your thighs.
Brands that are doing it right (and who to avoid)
You don't need to spend $400 on designer denim. In fact, the best long jeans shorts for men are usually the ones with some history.
- Carhartt WIP: Their "Landon" short is the gold standard right now. It’s heavy, it’s wide, and it’s built like a tank.
- Dickies: Look for the 13-inch Multi-Use Pocket Work Short. It’s technically a blend, but it gives that stiff, structural look that denim heads love.
- Polar Skate Co: The "Big Boy" shorts. These are extreme. If you want the authentic 90s skate aesthetic, this is it. They are massive, but they are incredibly well-made.
- Vintage Levi’s: Go to a thrift store. Find a pair of 550s or 560s (the "Relaxed" or "Comfort" fits) that are one size too big in the waist. Cut them at the knee. Congratulations, you have the best jorts in the world for $15.
Avoid the "mall brands" that try to fake the look with stretchy denim. If the tag says "2% Elastane" or "Spandex," keep walking. Baggy denim needs to be 100% cotton. The stretch makes the fabric "limp," and instead of hanging with authority, they just sag and wrinkle in all the wrong places. You want that "cardboard" feel. It breaks in over time and becomes yours.
The sustainability angle
One of the coolest things about this trend is how it encourages upcycling. We are in a waste crisis with clothing. Millions of tons of jeans end up in landfills because the "skinnies" went out of style. Taking a pair of "outdated" relaxed-fit jeans and turning them into long denim shorts is one of the most sustainable fashion moves you can make.
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It’s also an entry point into "slow fashion." A good pair of heavy denim shorts will last you a decade. They don't have a zipper that’s going to break after three washes or thin fabric that will rip when you sit on a concrete bench. They get better with age. The more you wear them, the more they mold to your body.
Common misconceptions about the "long" look
People think long shorts make you look shorter. It’s actually the opposite if you get the proportions right. A high-waisted, long denim short can elongate the torso-to-leg ratio.
Another myth: "They're just for kids."
Look, if you're 45, you probably shouldn't wear jorts that hit your ankles with a chain wallet. But a dark indigo, 10-inch inseam short with a crisp button-down shirt and some leather Birkenstocks? That’s a sophisticated summer uniform. It’s about the wash and the styling, not just the length.
Actionable steps for your next pair
If you’re ready to dive in, don't just buy the first pair you see on a mannequin.
Start by measuring your favorite pair of pants. Find the "rise"—the distance from the crotch to the waistband. For long jeans shorts for men, you want a "mid-to-high" rise. This allows you to wear them at your natural waist, which helps the shorts drape properly.
Next, check the "leg opening." This is the secret sauce. If the leg opening is less than 10 inches, they might feel a bit "tapered," which ruins the baggy aesthetic. Aim for 11 inches or more for that authentic wide-leg feel.
Finally, don't be afraid of the "break-in" period. Raw denim is stiff. It might feel like you're wearing a tent for the first three days. Wash them once, hang dry them, and keep wearing them. By week two, they’ll be the most comfortable thing you own.
Next Steps for the Perfect Fit:
- Check your local thrift store for Levi's 550 or 560 models.
- Measure your inseam; aim for at least 10 inches to ensure they clear the mid-thigh.
- Stick to 100% cotton denim to ensure the shorts maintain their structure and don't "cling."
- Pair with a "heavyweight" cotton t-shirt (250gsm or higher) to match the visual weight of the denim.