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How to Wear Men’s Denim Shorts in 2021 & Our Top Picks

How to Wear Men’s Denim Shorts in 2021 & Our Top Picks

What do you picture when you think about men’s denim shorts – that is, if you think about them at all?

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For men’s wardrobes, denim shorts attached themselves to those dad trends from a few years back.

They were intentionally frumpy – high waisted yet wider cut with an I-don’t-care attitude. However, traditional men’s denim shorts aren’t so much blasé as they are a practical-for-practical-sake style.

men wearing denim shorts

They’re for doing yardwork on 90-plus degree days, often accompanied by a stained T-shirt and comfortable-fitting sneakers.

Still, the dad façade has faded. The former irony has left us with high-waist pleated pants – more flattering this time around than back in the ‘90s – and boot-cut jeans. Denim shorts – or jorts, if you will – have lingered all the same.

But, rather than look like a pair of cutoff Levi’s 501s, they stand on their own with a proper, more modern silhouette. They’re less nostalgia around suburban middle-class living and more a denim version of all those shorter and chino cuts we’ve been seeing this year.

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

We’ve already mentioned this – they shouldn’t look like cutoffs. However, nor should they resemble some over-the-knee, late-‘90s monstrosity sported by teen skaters horrified by shorter inseams and a closer fit. 

You have more confidence (and better style sensibilities) now, and outside of these areas, a quality pair of men’s denim shorts tends to run slim, tapering down to the knees, if not falling above.

Just how high can you go? Think to the ‘70s or ‘80s with a five- to seven-inch inseam for reference.

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Within this general template, seek out a lighter-weight denim – after all, you will be wearing them in hotter, more humid weather. Consider the full range of washes – nearly bleached to dark indigo – and the many patterns out there. 

How to Wear Men’s Denim Shorts

man flaunting denim shorts

In general, look for something falling above the knee, if not shorter, and with a slimmer, tapered fit, rather than a boxy, wider cut

From here:

  • Denim shorts pair well with practically all casual shirts in your wardrobe. Everything from T-shirts to polos and patterned button-downs is fair game.
  • Don’t go retro, unless you plan to alter the silhouette. Older pairs of men’s denim shorts tended to bag and fan out, obscuring your entire mid-section from the waist to the knees. A slimmer cut, by contrast, lengthens your torso overall, helping you appear taller.
  • Experiment with different washes and patterns, keeping in mind the relationship between your shirt and bottoms.
  • Consider some workwear influences, particularly cargo pockets and painter’s pant elements.  

Our Top Picks:

Polo Ralph Lauren 6.5-Inch Polo Prepster Denim Shorts

Polo Ralph Lauren 6.5-Inch Polo Prepster Denim Shorts

Jorts meet gym shorts. The comfort you prefer as you get through your workout is all there, thanks to a fully elastic waistband with a drawstring for an adjustable fit and a wider, above-the-knee cut. From here, lightweight denim is distressed by hand for a more effortless feel that requires minimal breaking in.


Polo Ralph Lauren 7.5-Inch Sullivan Slim Denim Short

Polo Ralph Lauren 7.5-Inch Sullivan Slim Denim Shorts

Distressing, patching, and repairing have been all over men’s jeans, so why not denim shorts? This stiffer, more traditional material goes the DIY route, albeit in a more tasteful and tapered direction with rips and visible 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 close to dad’s yardwork pair as you can get. A modern update opts for slightly lighter stretch denim for more natural movement, plus a tapered fit for shape and a charcoal hue that’s been faded and distressed via laser. 


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 – midrise, so that it sits right above the hips, and extending nearly down to the knee. This fully cotton denim pair kicks it old school but more polished with a slim although not skinny fit and light distressing. 


True Religion Men's Ricky No Flap Short Se

True Religion Ricky Straight Shorts

From the slimmer, board short-like cut to the ripped hems, this pair of men’s shorts looks like something you’d spot on an episode of the Outer Banks. Add a Hawaiian shirt and haven’t-washed-in-days grime, and you’re ready to hit the beach (or maybe search for some gold). 


Wrangler Authentics Men’s Comfort Flex Waistband Short

Wrangler Authentics Men’s Comfort Flex Waistband Shorts

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The feel of work jeans, albeit more flexible thanks to a touch of spandex, gets a chino-length upgrade for everyday wear. With a 10-inch inseam, these approach old-school jorts, but the tapered fit and lightly faded appearance give them a more contemporary touch that doesn’t look out of place next to your polo. 


Levi's Men's Slim Jean Shorts

Levi’s Men’s Slim Jean Shorts

Levi’s knows what its audience wants when it comes to jean shorts. They’re not looking for something too flexible – but it should feel broken in a touch – but they don’t want true cutoffs, either. Based on Levi’s 505 silhouette, these shorts deliver with a slim, just-touching-the-knees fit with rolled yet more raw-looking cuffs, a midrise that hits above the hips, and definite distressing along the legs. 


G-Star Raw Men's Sato Denim

G-Star RAW Men’s Sato Denim Shorts

G-Star has delivered premium, raw Japanese denim for over 30 years, appealing to a more urban consumer with refined tastes. The Sato 3301 shorts don’t waver from this model, instead sticking with a classic five-pocket silhouette that’s been cut off and cuffed at the knee. It’s slim with a touch of space, and the denim’s aged to the point of fading and light distressing. 


Mavi Men's Jacob Mid Rise Slim Twill Shorts

Mavi Jacob Mid-Rise Shorts

At their length and slimness, you could call these shorts denim Bermudas. Where they excel is the variety of colors, applied with thicker, brushed cotton twill for a denim-like texture and feel with a touch of stretch. 

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