A Guy’s Guide to Shorts
By Megan Collins | Last Updated: Aug 4 2023 | 10 min read
When it comes to warm weather, every guy wants to be comfortable. And every guy who visits Style Girlfriend on the regular? Well, he wants to be comfortable and look stylish, too.
When you’re figuring out how to dress for summer as a guy, that generally means wearing as little as possible while still appearing appropriate for wherever you’re headed.
So adding cool, stylish men’s summer outfits with shorts to your wardrobe repertoire is a must.
Good news, SG has a plan for that.
Wondering how to look good in shorts?
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
- What to wear with shorts
- The best men’s shoes to wear with shorts
- Best places to buy shorts for guys
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.
I like the simple framework Art of Manliness has suggested on when it’s appropriate to wear shorts:
- When there’s a good reason to (temperature, environment, location) and
- 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.
But 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:
Instead, look for tailored shorts that fit you well.
That doesn’t mean your shorts should be painted on, though.
It just means they should fit – they shouldn’t be baggy and hanging off you, but you should still be able to sit and move comfortably in them.
How to dress with shorts
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
Like corduroy! GQ helpfully identified the Banks Journal shorts that Chris Pine is spotted in constantly in different colors.*
*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
You don’t need to be in the NBA to try a matching shorts and shirt set like Serge Ibaka.
Or on a tropical vacation. Really!
If you’re trying to navigate the best shirts to wear with shorts 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
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
If you’ve been trying to figure out how to wear denim shorts? We’ve got good news for you. Cut-off shorts and denim shorts are totally back in 2022! 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 Sabir Peele of Men’s Style Pro. 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
This one’s a no-brainer.
When it comes to what tops to wear with shorts, 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.
If you’re wondering how to style khaki shorts, this is also a great way to make shorts look a little more tailored.
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, we make no promise you’ll be able to stop yourself from trying more trends in your outfits!
> > Check out more ways to wear a short-sleeve button-up shirt this summer
6. Wear shorts with a sweater
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.
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 drawstring chino shorts: Old Navy, $30
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 Old Navy has been a long-time favorite of Team SG, but be aware: they sell out fast each season!
If you don’t see your size, check out this (just as good but a little more expensive) style from Madewell.
Best 5″ and 7″ chino shorts: Bonobos, $89
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, $75
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.
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:
- 5 ways to wear linen shorts
- 3 drawstring shorts outfits
- 5 ways to wear chino shorts
- How to wear athleisure shorts
- 7 pairs of 7″ #SGapproved shorts
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?
I started Style Girlfriend to help guys look, feel, and act their best.
