How to Wear Shorts: Style Tips and Outfit Ideas for Guys

A Men's Summer Style Guide

By Megan Collins | Last Updated: Jul 2 2019

When it comes to warm weather, every guys wants to be comfortable. And every guy who pops by Style Girlfriend on the regular? Well, he wants to be comfortable and look stylish, too. In the summer, that generally means wearing as little as possible while still appearing appropriate for wherever you’re headed. So figuring out how to wear shorts is a must. Good news, SG has a plan for that.

In this guide on how to wear shorts for men, you’ll discover:

  • When are shorts appropriate (and when you should skip ’em)
  • The right way for shorts to fit
  • Shorts outfit ideas for guys
  • The best shoes to wear with shorts
  • Shorts shopping suggestions

Ready? Let’s do this!

When are shorts appropriate?

A lot of guys think that shorts “aren’t okay” to wear. Some of this is an old-fashioned thing, but a good amount of concern comes from a desire to look appropriately outfitted in a given venue or setting.

So I like the simple framework Art of Manliness has suggested on when it’s appropriate to wear shorts:

  1. When there’s a good reason to (temperature, environment, location) and
  2. When you’re not conducting business or attending a formal ceremony/event

So: big presentation in even the most casual workplace? Probably best to skip shorts. Big day date with your lady at the lake? Shorts are absolutely a go!

How shorts should fit

So much of ensuring your shorts look stylish, rather than lazy, is in the fit.

When it comes to shorts length, you’ll find plenty of different takes from folks across the interwebz. A lot of menswear sites you’ll read will tell you that a 9″ inseam is the right way to go. But in 2019, that honestly feels overly conservative. We’ve been Team 7″ Shorts for awhile, and we’re sticking with it.

As for how shorts width, you may be used to the generous silhouettes of your youth. Think: tents of fabric from the likes of Hollister and American Eagle, with billowy cargo pockets and tails of fabric hanging off the sides. That is not how a grown man’s shorts should fit!

Instead, look for tailored shorts that fit you well. That doesn’t mean your shorts should be painted on, though. I like this guidance from men’s style blog Mocha Salt:

“When we say tailored, we don’t necessarily mean slim-fitting. We mean: everything needs to fit properly…in other words: it needs to fit as it was designed to fit. Don’t wear shorts that are two sizes too big and call them “loose”; fit is important no matter the cut you choose. You can wear a looser pair of shorts and still look tailored, as long as the fit is good.

Shorts outfit ideas for guys

Okay, so those guidelines are all well and good, but what about how to make an outfit with shorts look stylish?? Leveling up your summer style is about learning to create a proper outfit with a capitol-O instead of just…what you threw on before leaving the house. Check out the style inspiration below.

Wear shorts in a monochrome outfit

l to r: Modest Man Style, IG: Zach Miko, Extra Extra Style

A super-simple way to elevate your shorts outfit is by wearing one color or color family head to toe.

This is the easiest, don’t even have to go shopping way to make an outfit look more thoughtful and intentional than just pulling whatever t-shirt from the top of your drawer.

Wear shorts in an unexpected color or pattern

l to r: Notoriously Dapper, Levitate Style

Another way to make a shorts outfit more interesting is by wearing a pair of shorts that doesn’t look like anything else in your closet. Kelvin from Notoriously Dapper achieves a totally interesting and cool look by wearing what looks to be a pair of pretty standard chino shorts…in a bright, hi-vis green. Leo from Levitate Style wears vertical stripes (in neutral colors).

The rest of the looks are simple. A polo, slip-on sneakers, and a blue baseball hat for Kelvin, and a t-shirt and sneaks for Leo. Easy!

Wear cut-off shorts

via Men’s Style Pro

Another way to make shorts a little more interesting is to..literally make your shorts. Sabir from Men’s Style Pro fashioned these chinos into shorts himself. Here’s his tips for wearing jean shorts without looking like you stepped out of a time machine from 1992:

  • For your first attempt, try a light or dark wash that tailored and stop just above the knee.
  • Avoid distressing here, jeans shorts already make a statement
  • If you denim is a scary entry point, try a stretch chino (like the white one’s I’m wearing from Uniqlo with a DIY cut and wash)

Even if you buy your shorts pre-cut (you can find a few of our favorites here, here, and here), the look reads Robinson Crusoe-levels of fashion adventure.

Wear shorts with a short-sleeve button down

via Notoriously Dapper

Had to bring it back to Notoriously Dapper who is the summer king of the short-sleeve button-down shirt (aka an “SSBD”) and shorts.

Do you have to wear a big-ass hat like he does? No, but once you start experimenting with your style, there’s no saying you’ll be able to stop yourself.

Wear shorts with a sweater

l to r: Levitate Style, Extra Extra Style

Don’t think for a second that you can’t zhush up your shorts outfits at least a little. Returning to Levitate Style’s Leo and Ryan from Extra Extra Style, you’ll note two different ways to layer up.

I really love Leo’s cardigan with a henley and athletic shorts. It’s a great dressed-up/dressed-down vibe that’s unexpected yet stylish. And I love Ryan’s preppy and put-together outfit. So simple, too. Just a pair of chino shorts, belted with an oxford shirt and repp tie, with that sweater oh-so-casually tossed over his shoulders.

The best shoes to wear with shorts

You have options when it comes to figuring out how to wear shorts with the right pair of shoes for your outfit.

Sneakers – simple canvas sneakers or slip on vans are nice

Boat shoes – just watch your accessories before you turn into a background extra in Wedding Crashers

Espadrilles – you know we love these casual shoes

Penny loafer – here’s a few ideas on how to wear them

Driving moc – this has a bit of a dad vibe, if you’re into that kind of thing

How to wear different kinds of shorts

Okay, you’ve seen a few ideas above. But what if you want more specific ideas on how to wear shorts made of different kinds of fabrics and materials? Check out the list of links below:

Five ways to wear linen shorts

Five ways to wear chino shorts

How to wear athletic (or, cough, athleisure) shorts

Shorts shopping suggestions

This graphic from Primer Mag is a great way to know what you’re not looking for:

Ultimately, your shorts outfit is going to look as stylish as you decide you want it to be. This summer, why not level up your style by giving some care to even your most carefree looks?

Shop our favorite shorts for…

Best pre-rolled shorts: Topman, $35

Best overall: J.Crew 7″ stretch short, $65

Best short shorts: Chubbies 5.5″ stretch originals, $50

Best shorts for short guys: Peter Manning, $74

Best technical shorts you can wear all day: Rhone ‘Mako’ shorts, $68