How To Style Denim Shorts For Men in 2023

What comes to mind when you think of men’s denim shorts, if you think about them at all?

Denim shorts have become synonymous with those dad fashions from a few years ago in men’s wardrobes.

They were purposefully ugly, with a high waisted but broader cut and an I-don’t-care attitude. Traditional men’s denim shorts, on the other hand, aren’t so much blasé as they are a practical-for-the-sake design.

They’re for performing yardwork on 90-degree days, usually while wearing a dirty T-shirt and comfortable sneakers.

Even so, the dad persona has worn thin. The previous irony has given way to high-waist pleated trousers, which are more flattering now than they were in the 1990s, and boot-cut jeans. Denim shorts – or jorts, if you will – have persisted.

However, instead of resembling a pair of cutoff Levi’s 501s, they stand on their own with a proper, more modern silhouette. They’re less nostalgic for suburban middle-class life and more of a denim version of all the shorter and chino cuts Teeanime has seen this year.

What Makes a Good Pair of Men’s Denim Shorts?

We’ve already stated that they should not resemble cutoffs. However, they should not resemble some late-’90s over-the-knee abomination worn by teen skaters scared by shorter inseams and a closer fit.

You’re more confident (and have better style instincts) today, and outside of these regions, a good pair of men’s denim shorts should be slender, tapering down to the knees, if not above.

How high can you get? Consider the 1970s or 1980s, with an inseam of five to seven inches.

Within this basic framework, go for lighter-weight denim – after all, you’ll be wearing them in hotter, humid conditions. Consider the complete spectrum of washes available, from virtually bleached to dark indigo, as well as the numerous designs.

How to Wear Men’s Denim Shorts

In general, look for something that falls above or just below the knee and has a slimmer, tapered fit instead of a boxy, wider cut.

Start here:

  • Almost all of the casual shirts in your closet go well with denim shorts. Everything is fair game, from T-shirts to polos to patterned button-downs.
  • If you want to keep the same shape, don’t go retro. Men’s denim shorts used to be baggy and spread out, making it hard to see anything from the waist to the knees. A slimmer cut, on the other hand, makes your torso look longer, which makes you look taller.
  • Try out different washes and patterns, but keep in mind how your shirt and bottoms go together.
  • Think about some elements of workwear, like cargo pockets and painter’s pants.

Our Top Picks:

Polo Ralph Lauren 6.5-Inch Polo Prepster Denim Shorts

Polo Ralph Lauren 6.5-Inch Polo Prepster Denim Shorts

Jorts collide with workout shorts. A fully elastic waistband with a drawstring for an adjustable fit and a broader, above-the-knee cut provide the comfort you need during your workout. Lightweight denim is then manually distressed for a more relaxed feel that requires little breaking in.

Polo Ralph Lauren 7.5-Inch Sullivan Slim Denim Short

Polo Ralph Lauren 7.5-Inch Sullivan Slim Denim Shorts

Men’s jeans have been distressed, patched, and repaired, so why not denim shorts? This tougher, more traditional cloth takes the DIY path, albeit in a more refined and tapered manner, with rips and evident wear patched up with herringbone and twill.

Hugo Boss Tapered-fit shorts in gray stretch denim

Hugo Boss Tapered-Fit Shorts in Gray Stretch Denim

These are as near to your father’s yardwork shoes as you can get. A modern design includes slightly lighter stretch denim for more natural movement, a tapered cut for shape, and a charcoal shade that’s been laser faded and distressed.

Hugo Boss Blue Tapered-Fit Denim Shorts with Manifesto Logo Patch

Hugo Boss Blue Tapered-Fit Denim Shorts with Manifesto Logo Patch

This is the classic chino cut, with a midrise that rests just above the hips and a length that nearly reaches the knee. With a thin but not skinny cut and subtle distressing, this 100% cotton denim pair is old school yet more sophisticated.

True Religion Ricky Straight Shorts

From the smaller, board short-like cut to the shredded hems, these pair of men’s shorts seems like something out of an Outer Banks episode. You’re set to hit the beach with a Hawaiian shirt and clothes you haven’t washed in days (or maybe search for some gold).

Wrangler Authentics Men’s Comfort Flex Waistband Short

Wrangler Authentics Men’s Comfort Flex Waistband Shorts

Work jeans get a chino-length makeover for everyday wear, but more flexible thanks to a touch of spandex. With a 10-inch inseam, these are similar to old-school jorts, but the tapered fit and faintly faded appearance offer them a more modern feel that won’t clash with your polo.

Levi's Men's Slim Jean Shorts

Levi’s Men’s Slim Jean Shorts

When it comes to jean shorts, Levi’s knows exactly what its customers desire. They don’t want anything too flexible – but it should feel broken in a little – but they also don’t want actual cutoffs. These shorts, based on Levi’s 505 silhouette, have a narrow, just-touching-the-knees shape with rolled yet more raw-looking cuffs, a midrise that hits above the hips, and noticeable distressing throughout the legs.

G-Star Raw Men's Sato Denim

G-Star RAW Men’s Sato Denim Shorts

These shorts are long and slender, like denim Bermudas. Their diversity of colors and brushed cotton twill give them a denim-like texture and elasticity.

Mavi Jacob Mid-Rise Shorts

These shorts are long and slender, like denim Bermudas. Their diversity of colors and brushed cotton twill give them a denim-like texture and elasticity.