How to Wear Shorts: The Stylish Guide

Beating the heat while still looking cool

Written by Salvatore Marashi

As we know, there are some important rules for wearing shorts. One wrong move and you’ll be invoking grade school prep and not the stylish man we know you are. We get wanting to write off shorts altogether. Don’t be so fast! There’s no reason to relegate yourself to having sweaty claves all summer long. Let’s get you the right pair to bring shorts back into your rotation.

Classy Chino Shorts

No matter what situation, chino shorts are a good call. Just like their full-length counterpart, they have that special ability to dress up or down any look while simultaneously staying stylish. Tell me a crisp pair of off-white chinos won’t look great with a suit. Actually don’t tell me that, because you’d be wrong. As for styling, you’ll have a hard time going wrong. Anything from your favorite tee to an oxford will match perfectly. We suggest nailing the look with a breezy linen button down and some canvas sneakers.

Easy-Going Denim Shorts

Denim shorts can bring some unwanted flashbacks of dad style. When done right, however, they handle your summer adventures with ease. Sturdier than chinos, denim shorts are more than enough to handle all the water, sand and mud you can throw at them. This is good news for all you denim lovers out there because sometimes it’s just too damned hot to wear anything other than shorts. Take note that casual vibes are best with these, so pair with a favorite t-shirt and hoodie.

Make a Splash with the Right Swim Shorts

You don’t have to let your style suffer just to get out on the water. Gone are the days of baggy board shorts. Floral prints and stripes bring life back into the look. Slimmer fits work great but consider your height to length ratio. Also, a few leg days in the gym might be worth investing in.

Our Favorite Shorts

Gap Washwell Vintage Chino Shorts

We love the stylish simplicity of these shorts. With a tapered ending just above the knee, they are conservative without being too long. Better yet, if you end up loving them the same way we do, you can cop them in several different colors.

H and M Slim Fit Denim Shorts

If you’re like me, denim shorts bring back memories of bad barbecue fashion and clueless old guys. It doesn’t have to be that way though. Getting a cool pair is all about the fit and color. H and M envoke classic denim colors without them looking old fashioned all the while keeping things current with an up-to-date fit.

J-Crew Factory 6″ Swim Shorts

These J-Crew swim shorts are a great choice for heading out on the water. They’re slim enough to not way you down while being perfect for heading into town for food after. With classic colors like Navy, they are even more wearable.

What Shoes to Wear with Shorts

Wearing shorts comes with the added struggle of figuring out what shoes will look good with them. Unlike their longer counterparts, there are definitely shoes that work with the look and ones that don’t.

How to Wear Sneakers with Shorts

Sneakers and shorts go together like bread and butter. It’s a natural combination. While we love the look of minimalist sneakers, any type will work. Surprising this includes hightop sneakers. The only rule here is to pair with no-show socks. While wearing high socks with shorts isn’t the most egregious sartorial sin you could make, they are simply the less stylish choice.

Our Pick: Aldo Haener White Mens Sneaker

Loafers and Shorts

Sneakers won’t be right for every warm-weather occasion. Therefore, investing in a quality pair of loafers is a smart move. They bring a bit of formality to your look but still are casual enough to pair with shorts. Therefore, they look great with chinos, steering you clear from boyish and into style genius. With that said, loafers and jean shorts are a disaster waiting to happen. Hopefully, this didn’t need to be said but it’s important none the less.

Our Pick: H and M Brown Loafers

An Actually Cool Pair of Sandals

We all had that college friend who wore the same pair of grimy sandals every day. Don’t be like him. Before you go and end your relationship with sandals, there is a right way to wear them.

Leather sandals are your best bet. Just like loafers, they balance the fine line between formal and casual. Paired with some chinos and you have a smart look that would feel right at home on the Italian coast. Likewise, leather sandals are a great addition to swim trunk outfits or jean shorts.

A great pair of men’s sandals in black or brown leather make for a classic and versatile look.

Our Pick: ASOS Silver Street Double Strap Sandals In Black Leather

Short No-No’s

• Baggy shorts are not a good look. Where you may be able to get away with a pair of pants that don’t entirely fit you as they should, shorts are not that. As far as fit, they should come just above your knee. Going a bit shorter than that is okay too, just know that…
• Short-shorts are not good either. While you may be proud of everything you’ve got going on down there, no one wants to see that. Leave a bit to the imagination and get a pair that fit. Not only will women thank you for it but guys everywhere will appreciate your discretion.
• Bad colors are all too present in men’s short wear. Subtle is usually better when it comes to this. Flamboyant colors will draw attention to your legs so all you shorter guys will look, you guessed it, shorter and for my tall fellows, you’ll look even lankier.
• For some reason, designers think it’s okay to plaster shorts with all sorts of ridiculous designs. A rule to follow is if you wouldn’t wear that design on your pants, then you shouldn’t be wearing them on your shorts.
• I shouldn’t have to say this but wearing gym shorts with every outfit is not okay. Yes, I know they’re comfortable. In a perfect world, they’d look stylish outside of the house as well. Unfortunately, it doesn’t work that way. Keep those shorts for workout sheshes and for kicking back at home.

To Finish

It’s time shorts deserve some respect. With the right pair, you can look good while dodging the heat. Overall, know your aesthetic and put some thought behind your outfits. There’s no doubt that the right pair for you is out there. Just don’t be afraid to show off some leg.

What are your thoughts on shorts? Let us know in the comments below!

Salvatore Marashi

SOURCE: THE GENTLEMANUAL