how to wear shorts

Shorts can be a controversial item of clothing for men. Depending on where you live, shorts are either a must-have item or a rare and debatable choice. The question of how to wear shorts is an even more hotly debated topic. Should men wear white shorts? Can men wear shorts to a nice dinner? And is wearing shorts okay for a work event?

This article will answer all of these questions and more.

The Most Popular Types of Men’s Shorts 

Men’s styles come and go, but these types of shorts for men are all timeless options.

Cargo Shorts

These popular shorts have large pockets on either side, but they come in a range of styles and colors. Men's cargo shorts are a great look for both casual and work events depending on the cut.

Flat-Front Chino Shorts

These are a common style for shorts and often come in a variety of neutral colors like chinos do. Slim fit is the style of choice for these popular shorts.

Denim Shorts

These shorts have always been a staple of beach and fishing communities, but jorts are also making their mark in fashion. If you’re wondering what to wear with jean shorts, guys find this style easy to dress up or dress down when the weather gets warm.

Men wearing shorts made from linen, corduroy, and printed fabrics also bring rave reviews.

Bermuda Shorts

Bermuda shorts are sometimes called walk shorts or dress shorts.  Bermudas usually hit just above the knee and are sometimes worn with a blazer for spring and summer.


These popular SoCal shorts are long, loose swimming shorts. They have an opening in the front instead of the usual elastic waistband.

Swim shorts, running shorts, and cycling shorts are other popular athletic shorts that men sometimes wear to casual events.

Long Shorts

This super-casual style of shorts is easy to find at the local skate park. With the addition of upscale fabrics, they're also showing up on runways in fashion capitals around the globe. The hallmark of this shorts style is that they hit below the knee.

When Should Men Wear Shorts?

Shorts are usually for laid-back situations. A game at the local ballpark, a barbecue at the neighborhood park, or a round of golf are all places where you might spy a pair of shorts. If the sun is out, shorts provide some relief from the heat and a change of pace. 

At the same time, shorts are a fun way to push fashion boundaries. If you're a fashion-forward man, you might notice that shorts are showing up on the red carpet and other major events. Shorts are a fun alternative for moments where you want to show your less traditional side.

Times to Avoid Wearing Shorts

Unless there's an offsite retreat or you work in a very casual workplace, shorts are a no-go. As with any work attire, take a look at your peers and higher-ups, then make your own wardrobe choices accordingly.

The same rule of thumb goes for a night out for a fancy dinner or other situations where appearance matters. If you're known for pushing fashion boundaries, you might still throw on a pair of shorts in these scenarios. But for most of you, if you have to ask yourself should I wear shorts it's a good idea to save them for another time.

How to Wear Shorts

Wearing shorts is easy, but like many other styles, it's not what you do, it's how you do it. Men are sometimes hesitant about shorts because they’re often thought of as clothing for boys. But the comfort and versatility of a good pair of shorts should outweigh any reservations you might have. Let's talk about how to wear shorts for men.


Shorts should be the right length to highlight the best parts of your legs. If you have great quads you might want to show some leg, but usually men's shorts hit just above the knee. Athletic shorts are the exception here.


A straight leg and slim fit are goals for many shorts wearers, but comfort and functionality come in at a close second. No one is looking for a pair of streamlined cargo shorts, which are a prize for their pockets and comfort more than anything else.

As you start shopping, keep in mind that oversized shorts tend to make the parts they're covering look oversized too. This style can also look sloppy, especially if you're rocking shorts for a night out.

For fitted shorts, get a close fit in the seat. Legs should hang straight. A belt can help create a clean look, and so can some tailoring if your favorite shorts hang lower than you'd like.


The fabric for your shorts is important. If the point of your new shorts is keeping cool, a pair of polyester shorts is probably not the experience you're looking for.

Cotton is a great pick for breathability. There are many types of cotton — from madras to seersucker, and they're easy to wash and dry. Linen shorts are a great fabric for hot and humid weather but are also easy to wrinkle.

There are many new fabrics for shorts, like the nylon-spandex mix we use for our UB Tech Rainier Cargo Shorts that wick moisture while keeping their shape.


Sneakers with socks were once a big no. Sandals with socks were even worse. But again, it's not about what you do, but how you do it, and how well you know your crowd. Some excellent shoe and men's short pairings everyone will love include:

  • Show off your fancy sneakers with low socks
  • Grab some classic leather sandals
  • Put on a hiking sandal
  • Slip on your favorite flip flops
  • Penny loafers and mocassins are great sock-free with men’s shorts

6 Stylish Short Outfit Ideas for Men

If you’re new to fashion and are styling your shorts for spring and summer, check out these outfit ideas.

Surf-Ready Style

Pair a smart set of board shorts with a vintage tee, some quality flip flops, and a pullover hoodie.

Outdoor Life

The right jean shorts outfit for men’s summer camping weekends is easy. What to wear with denim shorts? Guys can combine a rugged pair of denim or corduroy shorts with a t-shirt, lined jean jacket, and hiking boots for a look that will last from the heat of day to a cool night by the fire.

Summer Dinner Look

Dining al fresco with your partner under the stars requires just the right look and you can easily dress up shorts. Men's chino shorts pair nicely with a long sleeve button-down shirt and a slick pair of boat shoes.

Boardwalk Bold

Wondering what to wear with white shorts? Guys can’t go wrong matching white shorts with a plain black mens shirt and black leather or canvas slip ons.

Summer Get-Together

Dress up your favorite pair of cargo shorts with a button-up Aero tech shirt, sunglasses, and a sharp pair of loafers.


If you love prints and bright colors, madras or linen shorts are a fun way to add some color to your look. Pair brightly printed shorts with a contrasting print button-down shirt or a tie-dyed hoodie for a one-of-a-kind statement.

Looking for the right outfit as the temperature rises? Discover the latest trends in shorts for men with UNIONBAY.