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How to Wear Men’s Shorts (With Style)

There is something to be said when a guy can wear shorts without looking like a child. Midway between swagger and sophistication, a great pair of shorts is the key to mastering summer style.

But how do you find that perfect pair, and what do you wear them with?

Turn to the experts. We’ve got you covered with the following guide on how to style shorts so you can take your summer style up a notch.

Quick Summary

Here are a few recommendations of shoes and shirts to wear with your shorts to get you started:

Shorts TypeRecommended Shoe TypeRecommended Shirt Type
Athletic ShortsAthletic shoes, SlidesT-Shirt, Hoodie
Denim ShortsCasual sneakersT-Shirt, Casual Button-Down, Hoodie
Chino ShortsCasual sneakers, Dressy Sneakers, Loafers, Dress ShoesPolo Shirt, Button Down, T-Shirt
Cargo ShortsCasual Sneakers, Flip Flops, Slip Ons, BootsLoose T-Shirt, Casual Button-Down
SwimmingBoat Shoes, Sandals, Flip FlopsT-Shirt, Tank, Button-Down

Athletic Shorts

When wearing athletic shorts, keeping the rest of your outfit simple and cohesive is important.

Up Top

Pair your shorts with a tee or tank top in a matching color scheme – bonus points if you match brands for both the top and bottom. Given the casual nature of athletic shorts, it’s best to avoid anything too flashy or over the top.

Footwear

Keep accessories to a minimum and choose athletic-centric sneakers such as running shoes, trainers, or slides. If there were any accessories you could get away with, it would be a pair of sunglasses or a hat – such as a snapback.

Color Scheme

You got a lot of options here. While we think monochromatic looks always work best with athletic shorts. You could also mix and match different shades of the same color – such as pairing navy shorts with a royal blue tee. Contrast is also an option. Try pairing your shorts with a white tee or tank and some low-top black sneakers.

Brands We Love Shopping From

Here are a few brands that we love when it comes to shopping for athletic shorts:

Looking for Outfit Ideas?

Here are some guys slaying the athletic shorts look:

athletic shorts
https://www.pinterest.com/pin/1970393576923181/
athletic shorts
https://www.pinterest.com/pin/404901822749352180/
gym shorts
Source: gymshark.com

Denim Shorts

Ah, the so-called jorts, once popular in the 1980s, then a brief renaissance in the early 00s, denim shorts are one of this year’s hottest trends.

And for a good reason too. Done right, denim shorts can give off major summertime vibes and help you stay cool in the heat. But before you head to the nearest store, you should know a few things about how to style denim shorts.

Up Top

Pair your shorts with a basic tee or tank. Again, we recommend going for something in a solid color to not overwhelm the look. You could also layer with a button-down shirt or lightweight sweater such as a hoodie.

We also recommend tossing on some polarized shades such as Ray-Ban Wayfarers.

Footwear

Again, keeping it simple is key. Opt for low-top sneakers if you can. Canvas sneakers from brands such as Vans or TOMS always work well. If you’re feeling a bit more daring, try out a pair of shoes from Oliver Cabell, Onitsuka, or Allbirds.

Color Scheme

Options here are a bit more limited when compared to other types of shorts. You could go for a classic look by pairing your denim shorts with a white or black tee. We also recommend solid shoe colors so they don’t compete with the shorts.

Brands We Love Shopping From

Here are some brands we love when it comes to shopping for denim shorts:

Looking for Outfit Ideas?

Here are some guys rocking the denim shorts look:

Denim Shorts
https://www.pinterest.com/pin/10766486602392016/
denim shorts
https://www.pinterest.com/pin/16184879902690195/
Denim Shorts
https://www.pinterest.com/pin/1055599903786728/
denim shorts
https://www.pinterest.com/pin/4996249577779745/

Chino Shorts

Name a short more versatile than the chino short. We’ll wait.

Ideal for both casual and dressier occasions, the chino short, like chino pants, can pretty much be worn with anything. But as with all clothing items, there are certain ways to style chino shorts, so you look your best.

Up Top

The world is your oyster here. Pair your shorts with a tee, polo shirt, or button-down shirt. We recommend going for something in a solid color so as not to overwhelm the look – although prints or patterns are definitely an option.

Match these with some sweet affordable aviators for bonus points!

Footwear

Again, you have a lot of options here. For a more casual look, try pairing your chino shorts with casual sneakers (not athletic). If you’re looking to dress things up, go for loafers, boat shoes, or even dress shoes like the monk strap shoe. Just make sure they’re comfortable enough to walk in.

Color Scheme

To pull off the chino shorts with style, be sure not to make things overly complicated. If you are wearing a patterned or printed shirt, we recommend solid-colored shorts and shoes. If you’re wearing patterned, printed, or plaid shorts, go for a solid-colored shirt and shoes.

Contrast, complementary, and monochromatic color schemes work well with chino shorts.

Brands We Love Shopping From

Here are some brands we love when it comes to shopping for chino shorts:

Looking for Outfit Ideas?

Here are some guys looking dapper AF in chino shorts:

chino shorts
https://www.pinterest.com/pin/749004981789354665/

chino shorts
https://www.pinterest.com/pin/24558760460699007/
chino shorts
https://www.pinterest.com/pin/6966574416409743/
chino shorts
https://www.pinterest.com/pin/210121138860601539/

Cargo Shorts

Like the denim shorts, cargo shorts were once popular and are now seeing quite a resurgence in popularity.

Typically made from a sturdy cotton fabric, cargo shorts are ideal for those who need to carry a lot of stuff with them on the go. But even if you don’t need all the pockets, cargo shorts can still make a great style choice.

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Pair your shorts with a basic tee, tank, or casual button-down shirt. Given that cargo shorts are bulky and contain several details, we recommend going for something in a solid color and a bit looser fitting.

Footwear

Cargo shorts come from a military background, so they tend to have a bit of a rugged feel. We recommend pairing them with sneakers or boots – something that has a bit of an edge to it.

Color Scheme

Neutral colors reign supreme when it comes to cargo shorts. Black, white, grey, and beige are all great choices.

Brands We Love Shopping From

Here are some brands we love when it comes to shopping for cargo shorts:

Looking for Outfit Ideas?

Here are some guys nailing the cargo shorts look:

cargo shorts
https://www.pinterest.com/pin/438467713732951275/
cargo shorts
https://www.pinterest.com/pin/56295064081802535/
cargo shorts
https://www.pinterest.com/pin/AZg2r91Z5WcIE0xf7UmGt719skcvvKKLA3uzgp7AuONWvTAD-NLINmg/
cargo shorts
https://www.pinterest.com/pin/908671662286636180/

Swim Shorts

Summertime calls for swim shorts. But what if you want to wear them outside the pool or beach? Or perhaps you were invited to a backyard barbecue and want to look presentable before diving into the pool after a few drinks?

No worries – swim shorts can easily be styled for various occasions. 

Up Top

Pair your swim shorts with a basic tee, tank, or button-down shirt. We recommend going for something in a solid color or a simple print. If the occasion is super casual, consider having fun with a tropical print or graphic tee.

You can even pair this with a nice sun hat for extra protection (and style).

Footwear

Pair your swim shorts with sneakers or flip-flops for a more casual look. If you’re looking to dress things up a bit, go for loafers or boat shoes.

Color Scheme

When it comes to swim shorts, anything goes. Have fun with prints, patterns, and colors.

Of course, if you are staying at a luxury hotel, having a weekend party with the boss, or going to a formal event, you’ll want to be a bit more conservative with your color palette. Solid matching colors and simple prints are always a safe bet – just don’t forget the sunscreen!

Brands We Love Shopping From

Here are some brands we love when it comes to shopping for swim shorts:

Looking for Outfit Ideas?

Check out these guys who know how to style swim shorts:

swim trunks
https://www.pinterest.com/pin/202028733275132711/

swim trunks
https://www.pinterest.com/pin/264164334383748537/
swim trunks
https://www.pinterest.com/pin/12525705200482226/

How Should Shorts Fit Your Body Type?

The first step to nailing the perfect pair of shorts is understanding what works for your body type. Not all shorts are created equal, and certain styles will work better for you than others.

Remember, guys, just like when buying a suit, it’s all about fit.

No one knows (or really cares) if you paid $50 or $500 for your shorts. If they look like a hot mess, it doesn’t matter how much you spent.

On the other hand, a great fitting pair of shorts will make you look like a million bucks – no matter where you got them.

When trying on shorts, keep the following key tips in mind:

  • If you’re on the shorter side, go for a mid-to-short length short. This will help extend your frame and make you appear taller.
  • If you’ve got bigger thighs, opt for tailored shorts with a bit of stretch. This will hug your legs in all the right places and make them appear more toned.
  • If you’re taller than average, you can get away with longer shorts. Just make sure it doesn’t go past your knee.
  • For a bigger belly, choose shorts with a higher waist. This will help to slim down your silhouette.
  • For bigger calves, avoid shorts that hit the widest part of your leg. Instead, go for a pair that falls just above the knee.

Ultimately, shorts should never be too baggy or too tight nor go past your knee.

Now that you know what to look for in a pair of shorts, it’s time to work them in with the rest of your wardrobe. Here are a few tips on how to style shorts so you can rock them all summer long.

Size Chart

Given that most shorts should sit just above the knee, knowing your inseam measurement is essential.

Here is a helpful size chart to use as a guide to finding the right inseam for your height:

Inseam LengthRecommended Height
5″5’5″ and Under
7″5’6″ to 5’9″
9″5’10” – 6’0″
11″Greater than 6′

These are only recommendations – not a hard rule. Going with the next shorter inseam (if you are 6′ and wearing a 9″ inseam) will always look great. The recommendations are only, so you aren’t wearing shorts that are too long for your frame.

Fits

When shopping for shorts, you’ll often find them available in three primary fits – regular, slim, and athletic.

Here’s a quick breakdown of each:

  • Regular fit: Also known as a classic or standard fit, this will be more relaxed through the thigh with a straight leg opening. It’s good for guys with larger thighs or those who don’t want their shorts to hug their legs too tight.
  • Slim fit: These are designed to hug your legs more closely and taper down at the knee for a slimming effect. This fit will be good for most men and is often the most aesthetically pleasing.
  • Athletic fit: If you are a guy that never skips leg day, you’ll want to look for shorts with an athletic fit. These will have a bit more room in the thigh and seat with a leg opening significantly wider than slim or regular shorts to allow for more movement.

Common Questions

Should shorts go past your knees?

No, shorts should never go past your knees. They shorten your appearance and make your legs look stumpy when they do. The only exception to this would be cargo shorts, they should hit right at the knee.

What color shorts should I buy?

Neutral colors such as navy, khaki, and olive green are always a good bet. However, you can also have fun with brighter colors such as red or green for more casual occasions.

Can I wear shorts to work?

In most cases, no. Shorts should be saved for more casual occasions such as the beach, backyard BBQs, or days exploring a new city. But, of course, if it’s a Zoom call, feel free to rock a pair of shorts from the comfort of your own home.

Can you wear socks with shorts?

You should always wear socks if you wear shoes of any kind with your shorts. Never go sockless as it can cause odor and fungus to build up on your feet. Men who give the appearance of a sockless style often wear no-show or invisible socks. These rest just below the collar of your shoe so they are not visible.

About Adam

As the lead editor of Tools of Men, Adam is an expert in all things men's grooming and style. When you don't find him reading up on the latest style trends, he likes to go jogging, attempt to distinguish the differences between IPAs, and play sports with his kids.

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