Let’s be honest. For about a decade, if you wore shorts that hit below the knee, people assumed you were either heading to a Limp Bizkit concert in 1999 or you’d completely given up on "fit." The fashion world moved toward 5-inch inseams that showed off way too much quad for the average guy to handle. But things change. Trends cycle back around, often with a weird sense of irony that eventually turns into genuine appreciation. Right now, men's denim long shorts—often called "jorts" by the internet—are having a massive, high-fashion moment that actually makes sense for the average wardrobe.
It’s not just about nostalgia.
When you look at brands like Our Legacy, Balenciaga, or even the resurgence of Levi’s SilverTab line, the silhouette is shifting. We are moving away from the restrictive, slim-fit aesthetic of the 2010s into something much more comfortable and, frankly, much more forgiving. You’ve probably seen the "Adam Sandler Summer" memes. While Sandler’s look is the extreme end of the spectrum, it tapped into a universal desire to stop wearing clothes that feel like a second, tighter skin.
Why the Proportions of Men's Denim Long Shorts Actually Work
Most guys are terrified of looking shorter. That’s the big fear with a long short, right? If the hem creeps past the kneecap, you worry your legs look like stumps. But here’s the thing: it’s all about the width of the leg opening and the weight of the denim.
If you wear a long, skinny denim short, you look like you’re wearing capris. That is a disaster. Don’t do that.
However, a wide-leg men's denim long short creates a vertical line that grounds an outfit. Think about the skate culture of the 90s. Brands like Blind or early Volcom weren't just being rebellious; they were wearing gear that could take a beating and allowed for a full range of motion. Heavyweight 14oz denim provides a structure that flimsy nylon shorts just can't match. When the fabric has some heft, it drapes away from the body. This creates a boxy, architectural shape that actually balances out a larger upper body or an oversized tee.
The Rise of the Jort 2.0
We have to talk about the "Big Boy" shorts from Polar Skate Co. These are arguably the catalyst for the current obsession. They are baggy, they are long, and they feature a specific embroidery on the change pocket that has become a status symbol in streetwear. But they aren't the only ones. Louis Vuitton’s recent collections under Pharrell Williams have toyed with denim shorts that look like they were cut from a pair of carpenter pants.
It’s a mix of workwear utility and sheer comfort.
If you're skeptical, look at the street style from the last few Copenhagen Fashion Weeks. You’ll see guys pairing dark wash men's denim long shorts with crisp loafers and white socks. It sounds insane on paper. In practice, it looks intentional. It looks like you know the rules well enough to break them.
Breaking the "Dad at a BBQ" Stigma
The biggest hurdle for most men is the association with the uncool dad look. You know the one: medium wash, elastic waist, maybe some velcro sandals. To avoid this, you need to focus on the finish of the denim.
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Raw denim or "dry" denim is a great entry point. It’s stiff. It’s dark. It looks expensive because it is. When you wear a pair of raw men's denim long shorts, the garment maintains its shape rather than sagging. As you wear them, they develop personal fade patterns—honeycombs behind the knees and whiskers at the crotch—that tell a story. It’s a way to participate in the "heritage" menswear movement without sweating through a pair of 21oz Japanese selvedge jeans in July.
Another trick? Cut-offs.
There is something inherently more "fashion" about a raw hem. Taking a pair of old, baggy vintage Levi's 550s and hacking the legs off right at the top of the calf creates a DIY aesthetic that feels authentic. It doesn’t feel like you bought a "style," it feels like you made a choice.
The Technical Side: Inseams and Rise
Let's get into the weeds for a second. When we talk about "long" shorts, we are generally looking at an 11-inch to 13-inch inseam.
For the average guy (around 5'10"), an 11-inch inseam will sit right at the top of the kneecap. A 13-inch inseam will cover the knee. If you go much longer than 13 inches, you're entering the territory of "shorter pants," which is a much harder look to pull off unless you're specifically going for a subculture-specific vibe like 90s hip-hop or modern-day Tokyo street style.
The "rise"—the distance from the crotch to the waistband—is equally vital.
- Low Rise: Generally avoid this for long shorts. It can make your torso look weirdly long and your legs even shorter.
- Mid Rise: The safe zone. Sits at the hip.
- High Rise: The pro move. Wearing a high-waisted men's denim long short allows you to tuck in a shirt, which defines your waistline and keeps the "long" shorts from making you look like a rectangle.
Footwear is the Make-or-Break Factor
You cannot wear slim, low-profile shoes with baggy denim long shorts. You just can't. If you put on a pair of slim canvas sneakers like Vans Authentics or All-Stars, your feet will look like tiny toothpicks sticking out of two giant blue denim tubes.
You need visual weight.
Think chunky. New Balance 990s, Salomon trail runners, or even a heavy-duty boot like a Dr. Martens 1461. If you're feeling bold, a lug-sole loafer provides the perfect counter-balance to the ruggedness of the denim. The goal is to make the transition from the wide leg opening to the shoe feel seamless, not like a sudden drop-off in volume.
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Misconceptions About Heat and Comfort
"Isn't denim too hot for summer?"
Kinda. But also, no.
Tight denim is hot. When fabric is pressed against your skin, there’s no airflow. However, wide-leg men's denim long shorts actually allow for a significant amount of air circulation. Because the leg opening is so wide, every time you walk, you’re basically pumping air up into the garment. It’s a chimney effect.
Also, look for "left-hand twill" denim. It’s woven differently than the standard right-hand twill and tends to feel much softer and more breathable right off the rack. Brands like Naked & Famous often experiment with these different weaves and even blends that include linen or hemp, which are game-changers for hot climates.
How to Style Them Without Looking Like a Caricature
If you’re worried about looking like you’re wearing a costume, keep the rest of the outfit simple.
A heavyweight white t-shirt is the gold standard. It matches the "weight" of the denim. If the shirt is too thin, it looks flimsy against the shorts. If you want to level up, try a boxy, short-sleeve button-down—maybe a camp collar shirt with a bold print. The key is that the shirt should also be somewhat oversized. Sizing up in your shirt helps maintain the "oversized" silhouette throughout the whole body so the shorts don't look like an accident.
Specific brands to check out if you're ready to buy:
- Carhartt WIP: Their "Landon" short is the gold standard for a heavy, workwear-inspired long short.
- Levi's: Look for the 468 Loose Short. It’s specifically designed for this trend.
- Stüssy: They consistently nail the California-skate-meets-high-fashion vibe with their denim offerings.
- Dickies: Not technically denim usually, but their 13-inch multi-pocket work short is the spiritual cousin of the denim long short and offers a similar silhouette.
The Sustainable Angle
One of the best things about the rise of men's denim long shorts is that you probably already own the raw materials.
The vintage market is flooded with 90s jeans that have slightly frayed hems or holes in the knees. Instead of throwing them out, you cut them. This is the ultimate sustainable fashion move. You’re extending the life of a garment that already has "character"—meaning the denim is already broken in and soft.
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Go to a thrift store, find a pair of "relaxed fit" jeans two sizes too big for you, grab some fabric scissors, and go to town. Don't worry about a straight line. The imperfections are what make them look "real."
What to Avoid at All Costs
While I'm an advocate for the look, there are some hard "no" zones.
Avoid pre-distressed denim with giant "designer" holes. It looks dated. You want the distressing to look like it happened because you actually did something, not because a laser in a factory hit it. Also, stay away from "stretch" denim in a long short. The beauty of this look is the structural rigidity of 100% cotton. Stretch denim tends to cling to the thigh before flaring out, which creates a very strange "bell-bottom" effect for your shorts.
Nobody wants that.
Lastly, watch the pockets. Cargo pockets on denim shorts can get very heavy, very fast. Unless you’re actually carrying tools, skip the extra bulk. The classic five-pocket setup is all you need.
Practical Steps to Nailing the Look
If you're ready to give men's denim long shorts a try, don't just dive into the deepest end of the pool immediately. Start with a pair that hits just at the top of the knee in a darker wash.
First Step: Go to your local thrift store and find a pair of Levi's 550 or 560 jeans. These have a naturally tapered but baggy leg.
Second Step: Put them on and mark a line about two inches below where you want them to end.
Third Step: Cut them with sharp scissors.
Fourth Step: Throw them in the wash immediately. This will fray the edges naturally.
Fifth Step: Pair them with a chunky sneaker (like an Asics Gel-Kayano) and a slightly oversized, plain hoodie or tee.
Take a look in a full-length mirror. You'll notice that the extra length and width don't make you look shorter—they make you look like you're dressed for the world as it is in 2026, not 2016. It's a silhouette that prioritizes the person wearing the clothes over the "rules" of traditional tailoring. And honestly? It's a lot more fun to wear.
Once you get used to the freedom of a wider leg, going back to 7-inch "Chubbies" style shorts feels like putting on a pair of wetsuit bottoms. Embrace the length, watch your proportions, and stop worrying about what the "short shorts" crowd thinks. They're probably just jealous of your pocket space anyway.