How to Wear Shorts: Style Tips and Outfit Ideas for Guys
A Men's Summer Style Guide
men's shorts outfits

By Megan Collins | Last Updated: Aug 10 2020

men's shorts outfits

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?

how to wear linen shorts

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 office (when we’re back in offices, that is)? 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 5-7″ Shorts for awhile, and we’re sticking with it.

As for shorts width, you may be used to the generous silhouettes of your youth.

Think: tents of fabric with billowy cargo pockets and tails of fabric hanging off the sides. That is not how a grown man’s shorts should fit!

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

primer mag things to avoid graphic

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.

1. Wear shorts in an unexpected color, pattern or fabric

via GQ

Recently, GQ helpfully identified the Banks Journal shorts that Chris Pine has been wearing in different colors* this summer.

*Great strategy, btw! Once you find something you like and makes you feel like a million bucks, buy it in as many colors as you can afford!

The $65 style comes in corduroy, which isn’t exactly what you’d expect from shorts. No disrespect to your standard chino shorts – they’re a men’s summer wardrobe essential! – but this kind of style somethin’-somethin’ is exactly what can help elevate an outfit from humdrum to handsome.

Consider adding to your thigh-baring repertoire with a pair in a bright, hi-vis color, stripes, or, yes, even corduroy.

Then, keep the rest of your outfit simple. A t-shirt or breezy button-up work just fine for Pine.

2. Wear shorts as part of a two-piece matching set

Instagram: Russell Westbrook

You don’t need to be in the NBA bubble to try a matching shorts and shirt set like Russell Westbrook.

This trend is an SG HQ fave because it’s so easy. You don’t have to worry about anything but what shoes to wear!

>> Check out #SGapproved matching sets

3. Wear shorts in a monochrome outfit

shorts outfits 2019
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.

4. Wear jean shorts or cut-offs

how to wear cutoff shorts
via Men’s Style Pro

Cut-off shorts and jean shorts are totally back in 2020! Yes, it’s a little hard to wrap your head around, I know. Let me give you a minute…

If you want to make your own cut-offs, follow these tips from Men’s Style Pro Sabir Peele. He fashioned those shorts above himself:

  • For your first attempt, cut a light or dark tailored wash of pants, stopping just above the knee. You can always cut again once you try them on, but you can’t add length back!
  • Avoid distressing here, jeans shorts already make a statement
  • If denim is a scary entry point, try a stretch chino first.

5. Wear shorts with a short-sleeve button down

how to wear shorts with a short sleeve button up shirt
via Notoriously Dapper

This one’s a no-brainer. Of course you can always wear shorts with a simple t-shirt or polo, but a short-sleeve button-up shirt helps you look a little more put together with barely any effort.

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

> > Check out more ways to wear a short-sleeve button-up shirt this summer

6. Wear shorts with a sweater

how to wear shorts with a sweater, dressy shorts outfits
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. Check out Levitate Style’s Leo and Ryan from Extra Extra Style above; 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.

clothes hanger

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 – These slip-ons offer a bit of a dad vibe, if you’re into that kind of thing

Shop SG’s favorite men’s shorts

Best 5″ and 7″ chino shorts: Bonobos, $78

bonobos khaki chino shorts

SG Says: When it comes to classic chino shorts, put Bonobos at the top of your list. They offer a tailored style in 5″ and 7″ inseams (and longer too, but let’s ignore those) in a variety of colors.

Best athleisure shorts: Olivers Apparel, $68

SG Says: The athleisure short is a great complement to pretty much any summer outfit.

Especially this summer when your co-workers are seeing you only from the waist up, you might as well go for a comfortable, breathable pair of shorts.

Best drawstring chino shorts: Save Khaki, $95

save khaki twill shorts

SG Says: The compromise candidate. When you want to look more put together but don’t want to fumble with buttons, go for a drawstring short in twill, linen, or some other easy-breezy fabric.

This pair from Save Khaki has been a favorite of SG followers all summer long, but is selling out fast. If you don’t see your size, check out this (just as good but a little more expensive) style from Todd Snyder.

More Men’s Shorts Outfit Ideas

Okay, you’ve seen a lot of ideas on how to wear shorts 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:

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?