Denim shorts are an absolute summer staple, a go-to favorite for fashionistas everywhere—ladies and gentlemen alike. When summer rolls around, you’re always on the lookout for something comfy, breezy, and effortless, right? Well, denim shorts have made their big comeback, and trust me, they’re bringing some serious game in 2020s.

Forget the frumpy, baggy dad-style denim shorts of the ’80s—those are ancient history. Men (yes, millennials and Zoomers, we’re looking at you) are rocking these shorts in a fresh, tailored, and super neat way. It’s all about combining form and functionality, folks.

Summer’s heat can be a challenge, but denim shorts are here to save the day, offering a breezy and stylish way to beat the heat. Before we dive into our pick of 25 uber-cool denim shorts outfits for men, let’s kick things off with a quick rundown on how to wear them the right way.

How to wear denim shorts:

Fit:
The modern denim short isn’t baggy, too long, or uncomfortably short. It’s tailored, ending just above the knees with a slight taper at the ends. Anything shorter? Big no-no, my friend—you’re not auditioning for a retro beach movie!

What Goes with Denim Shorts:
When it comes to tops, denim shorts are as versatile as it gets. Tees, tanks, hoodies, button-downs—basically, if it’s casual, it works. Short-sleeve shirts are especially a vibe, and layering an open button-down over a tee? That’s an instant win. Footwear-wise, you’ve got options: sneakers, boat shoes, loafers, even sandals. Pro tip: ditch the socks, or if you must, go for no-show ones—trust me, it’s a game-changer.

When to Wear Denim Shorts:
These shorts are your casual go-to, perfect for vacationing, hitting the beach, or chilling at a campsite. If the occasion calls for relaxation and a laid-back vibe, your denim shorts are up for the job.

How to Make Them Look Better:
It’s all about the details, bro. Accessorize and color-coordinate to level up your outfit. Feeling bold? Pair your shorts with an exotic casual shirt like a Dashiki or a kimono-style shirt for a standout look. Add a baseball cap, bucket hat, or some killer sunglasses, and you’ve got yourself a summer-ready style.

Caring for Denim Shorts:
Let’s be honest—denim shorts (and jeans) have historically been the unsung heroes of men’s wardrobes. They’ve been neglected, tossed around, and underappreciated for far too long. It’s time to change that. After a few sun-soaked outings, show them some love and toss them in the laundry. A little TLC goes a long way in keeping them looking fresh and feeling breezy!

         25 dapper denim shorts outfits for men

Own the chill with an unbuttoned shirt over a tee with denim shorts: 

Sure, rocking a simple tee with these shorts is a no-brainer, but why be the basic b*tch (oops did I say that out loud?), when you can elevate the look effortlessly? Just throw on a buttoned shirt up top and get a blend of nonchalance and style at its best! And your top shirt can be anything from a denim shirt to those expressive and elegant floral or tropical print shirts, full-sleeved or short-sleeved, it’s all about adding that little extra flair to your outfit. 

Slay in simplicity: with tees and denim shorts: 

A tee with denim shorts and a killer pair of clean summer shoes? Now that’s a basic combo that’s anything but boring! A crisp tee and denim shorts are basically soulmates, and when you toss in your sharpest summer footwear and match it up with the tee, you’re all set to slay with effortless style. Summer’s the perfect season to let these easy-going essentials steal the spotlight!

Going bold and brilliant with tank tops and denim shorts:

 Nothing oozes effortless sexiness quite like a bold combo of tank tops and shorts. Let’s be real—this look isn’t for the faint of heart. Rocking this duo means you’re ready to show off those arms you’ve been working hard on (we see you!). Check out these outfits that scream summer cool, confidence, and just the right amount of swagger.

The layered stint: 

Who says denim shorts are just for scorching hot days? You can totally rock them when the weather cools down a bit or even for the heydays of spring! Just toss on a puffer vest or any sleeveless top over a tee, or go for a light jacket or comfy hoodie—whatever floats your boat. Throw in some cool accessories like a baseball cap or a beanie, and boom—you’re all set to keep the vibe fresh and stylish, no matter the temp!