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?
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 2024, that feels overly conservative, and frankly, out of touch with modern men’s style.
We’ve been Team 5″ 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 the shorts to avoid:
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 prints! And patterns!
The textured jacquard style above 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 these shorts add an intriguing 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
linen matching set
cotton eyelet matching set
You don’t need to be on a beach or poolside at an all-inclusive resort nibbling on chicken fingers by the pool to sport a fun matching set like the ones above.
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!
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 2024! 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 bright color like in the above inspo pic?
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!
6. Accessorize your shorts outfit
Don’t think for a second that you can’t zhush up your shorts outfits at least a little.
Add a necklace, a hat, your favorite watch. Anything to take a casual look and make it feel more intentional.
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
Sandals – Skip the flip-flops and opt for a Birkenstock or other elevated open-toe shoe
Shop SG’s favorite men’s shorts
Best drawstring chino shorts: Abercrombie & Fitch All-Day Pull-On Shorts, $60
SG Says: The consensus 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: Flint and Tinder 365 Shorts, $78
SG Says: When it comes to classic chino shorts, put Huckberry’s in-house brand Flint and Tinder at the top of your list. Their 365 Short comes in 5″ and 7″ inseams (and longer too, but let’s ignore those) in a variety of colors. Perfect for everyday wear.
Best athleisure shorts: Patagonia Baggies (5″), $65
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 here.
But what if you want more specific ideas on how to wear shorts made of different kinds of fabrics and materials?
Well, great news.
You can check out even more #SGapproved summer style features. Just click on any link 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?
