Wearing shorts is one of the best ways to stay cool and casual when it’s hot outside. Here’s how to wear shorts properly (and how your shorts should fit).

Shorts are perfect for weekend shenanigans, dog walks, the beach, the pool, barbecues, picnics, romantic walks in the park…you get the point.

Shorts are inherently casual, but that doesn’t mean they have to look adolescent and sloppy. So why do most men look so bad wearing shorts?

Well, they’re just not wearing them correctly. Their shorts don’t fit properly, and they’re not wearing the right styles.

This guide teaches you how to avoid these mistakes so you look amazing wearing shorts, just like the laid back, stylish gent you really are!

Table of Contents

Let’s start with the length…

Shorts Length: How Long Should Men’s Shorts Be?

Just like with swim trunks, it’s crucial that your shorts don’t go past your knees.

They should stop at the top of your kneecaps (at the longest).

I like my shorts a little shorter, so most of my short stop 2-3 inches above my knees. This is a matter of personal preference, but I don’t think any man looks good with shorts that go past his knees.

Just like pants, the length of your shorts is measured along the inseam. The best length for men under 5’9? is 7?.

Anything longer than that will most likely be too long, although you can get away with 9? shorts if you like them a little longer.

If you’re under 5’5? or just want to show a little more thigh (highly recommended) you might want to wear 5? shorts instead.

Shorts Width (Leg Opening)

After wearing shorts that are too long, the second most common mistake that guys make is wearing shorts that are too wide.

Just like pants, many mass-manufactured shorts will be too wide through the leg. Unless you have thick legs, you’ll need to look for “slim fit” shorts or get your shorts tailored.