How to Style Shorts: The Complete 2021 Guide For Modern Men

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by  Savarone Ammann | Last Updated: 

A wise man once said “life is short, so wear shorts!”…alright, so I made that one up.

And there’s no question that shorts are more casual than pants. But they don’t need to be less stylish. 

For casual gatherings in warm weather, you can and should reach for shorts. The key is having quality shorts that pair well with the rest of your outfit.

What You’ll Need to Style Shorts Properly

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The most important factor in pulling off shorts is having the right shoes. If your shoes accent and elevate the shorts you’ve got on, then you’re halfway there.

SeaVees Hermosa

Made with rugged oiled leather, the Hermosa blends durability with laid back style. The Kona colorway is versatile and looks just as good with jeans as it does chinos and shorts.

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Next comes shirt selection, and finally, picking between various styles of shorts and making sure all of the ones in your closet fit. 

An intuitive rule to follow for styling shorts is to pick a vibe and stay consistent. Pair dressier shorts with dressier shirts and shoes. Pair athletic shorts with casual and athletic shirts and shoes. 

Here’s exactly what you’ll need to style your shorts right. It’s time to shed some fabric fellas.

How to Match Your Shoes and Shorts

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Be sure to match the style of your shoes with the style of your shorts. This might sound like common sense, but a lot of guys fail to do this.

For example, if you’re wearing dressier, fabric shorts, reach for stylish sneakers or slip-ons, loafers, or espadrilles. 

If you’re wearing athletic shorts made out of a technical fabric, you’ll want to toss on athletic sneakers, runners, or casual slip-ons. Be consistent and intentional.

Shoes to Wear With Chino Shorts

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Let’s get this out in the open.

Boat shoes look fine with shorts, but they’re ridiculously common and have really just become boring to look at. Boat shoes are passable, but they won’t make you look stylish or intentional with how you got dressed that morning. 

We can do better than that, guys.

You can stand out while still being subtle and classy. For truly timeless footwear, pick any shoe from SeaVees’ “The Classics” line. The shoes in this line will beautifully accent every color of shorts in your closet and give you the comfortable, dappered-down look you want.

My two favorites are the Hawthorne Slip On and the Hermosa Sneaker.

mens hawthorne slip on sneaker standard true navy 4 copy

The Hawthorne Slip On is an elegant, airy, slip-on made of cotton poplin twill. Both poplin and twill are woven fabrics that are soft, breathable, and strong. The outsole is composed of a firm natural rubber that’ll hold up well over time.

The Hermosa Sneaker is a low-top lace-up sneaker with as simple and iconic of a look as you’ll find anywhere. This version has a canvas upper and a rubber sole. The Hermosa Sneaker comes in black, beige, navy, and grey, which will accent every pair of subdued or bold-colored shorts you could ever have in your wardrobe.

SeaVees Hermosa

Made with rugged oiled leather, the Hermosa blends durability with laid back style. The Kona colorway is versatile and looks just as good with jeans as it does chinos and shorts.

Check Best Price Read Our Review
If you click this link and make a purchase, we earn a commission at no additional cost to you.

I’d say you are safe to wear both the Hawthorne Slip On and Hermosa Sneaker with low-cut socks, no-show socks, or no socks at all.

Remember, shorts are not dressy. They are inherently a casual wardrobe item. But if you’re after a slightly dressier look with the shorts you’ve got on, then pair them with loafers.

M.Gemi is making a tasteful, durable leather loafer that I really like the look of called the Sacca.

Best loafers for men m.gemi sacca

With loafers, aim for less material. Keep it minimal and slim and avoid chunky additions. 

Shoes to Wear with Athletic Shorts

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Athletic shorts are the pinnacle of men’s comfort and versatility. The perfect item for laying out to catch a football, lounging on the couch, walking around on the weekends, and for when you need to slip something on quickly for a last-minute run to the grocery store.

Most guys get home from work and are instantly relieved upon changing into athletic shorts. But when you wear them outside of the house, what kind of shoes should you pair with them?

Staying true to our rule of being consistent and intentional, you want to pair casual or athletic shoes with athletic shorts to match the vibe. If your shorts are colorful, then opt for black, grey, or white shoes and vice versa. 

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Athletic shorts should lay cleanly against your legs with a few flat or hidden pockets, sometimes with a zipper. Aim for shorts with a light, airy material to get the most out of this men’s comfort staple.

Because athletic shorts are a minimal item, you can pair them with bulkier, more noticeable athletic shoes.

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If you don’t want to look like you’re about to go for a run or suddenly leap up onto a box, you can pair athletic shorts with casual sneakers too. Go for something understated and simple like SeaVees’ Legend Sneaker.

SeaVees’ Legend Sneaker is an iconic men’s casual sneaker with understated laces and simple construction.

SeaVees The Legend

This is the original sneaker that kicked off the canvas sneaker craze in Southern California.

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Best Shirts to Wear with Shorts

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Luckily, choosing a shirt to wear with shorts is very similar to choosing a shirt you’d wear with pants. Most of the same guidelines apply such as not wearing conflicting patterns or colors.

Though, there are a few subtle things to keep in mind. For example, while you can pretty easily pull off a short or long-sleeved button-down with pants, a long-sleeve button-down with shorts tends to look awkward. With the right breezy linen shirt, you might be able to get away with cuffing or rolling the sleeves, but generally, a short-sleeve button-down will look much cleaner with shorts.

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Following our rule to be consistent and intentional, try to wear a shirt that matches the vibe of your shorts and shoes.

Wear a v-neck, a polo, or a short-sleeve button-down with nicer, fabric shorts. I love to wear solid black fabric shorts with a floral-patterned short-sleeve button-down or any shirt with a pop of color. State & Liberty makes high-quality short-sleeve button-downs that are built to be left untucked which is perfect for shorts.

State and Liberty 15

With athletic shorts, consider wearing a clean white or black t-shirt or an athletic shirt made of a technical fabric.

If you pair a polo with athletic shorts and shoes, it’s going to look clunky and misfitting.

Finding Shorts that Fit

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The fit of your shorts is as important as how you style them and what you pair them with.

One of the best ways any guy can elevate his sense of style is simply by wearing clothes that fit him well. When garments are baggy and oversized, they make you look baggy and oversized.

When garments are so short or tight they’re about to split open at the seams, you’ll look like a wannabe Hulk in a rather unflattering way. 

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Unlike pants, shorts don’t typically come in a wide range of fits such as slim, skinny, or relaxed. With shorts, you’ll pick out your standard waist measurement and the length of the inseam and that’s about it.

You’ve probably heard people say that men’s shorts should fall 1-3 inches above the knee, and that’s not a bad rule to live by. To find a pair that fits right, you have to know the length of your inseam.

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The inseam determines how long your shorts will be and is perhaps the single most important factor in picking out a pair. There’s loads of debate in the fashion world over what the best inseam length is for a pair of men’s shorts.

Most proper guys’ shorts—both chinos and athletic—will have an inseam somewhere between 5 and 9 inches. 

A 5-inch inseam is short, frisky, and fairly confident. It says “I’ve got good-looking legs, and I’m letting these puppies breathe.”

A 9-inch inseam, on the other hand, is much more conservative. It says “hey, don’t be looking too closely at my knees, okay?”

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Ultimately, pick whichever length you are comfortable wearing. The best length is whatever makes you feel the most confident and presentable.

I generally stick with a 7-inch inseam which falls somewhere in the middle. Do I think my legs are a beautiful sight for sore eyes? Uh, no not exactly. But I also don’t think they’re ugly. To me, it looks best when shorts fall about 2-inches above my knees. 

But shorts are called “shorts” for a reason. Don’t get caught wearing them too long. Shorts that cover the knees look disheveled and messy. You don’t want whatever’s covering your lower half to be in some grey zone between shorts and pants. 

In Short, That’s All You Need

Shorts can be a tricky item to integrate into the male wardrobe. But for warm-weather gatherings, they’re an essential garment. How you style them makes all the difference.

Be consistent and intentional. Pick a vibe and stick with it from your shirt to your shorts to your shoes.

When wearing chino shorts, elevate your look by reaching for a polo, a short-sleeve button-down, or a nice t-shirt. Throw on dressier sneakers, loafers, or espadrilles to complete the fit.

SeaVees Hermosa

Made with rugged oiled leather, the Hermosa blends durability with laid back style. The Kona colorway is versatile and looks just as good with jeans as it does chinos and shorts.

Check Best Price Read Our Review
If you click this link and make a purchase, we earn a commission at no additional cost to you.

When wearing athletic shorts, be sure your whole outfit exudes a casual and athletic vibe. For this look, go with a t-shirt made with a performance fabric and a pair of casual or sporty sneakers. 

Whatever you do, pick shorts that make you feel confident and comfortable. Gents, enjoy that fresh air and sunlight on your legs, you deserve it.

FAQs

How do you style shorts for men?

Be consistent and intentional when styling an outfit with shorts. If you’re wearing fabric shorts, pair them with a short-sleeve button-down and nicer sneakers. If you’re wearing athletic shorts, pair them with an athletic shirt and shoes.

How should men wear shorts?

Pick a short that falls a few inches above your knees. You want to wear shorts that match the entire vibe of your outfit. This means you should pair nicer, fabric shorts with nicer shirts and shoes and casual, athletic shorts with athletic shirts and shoes.

What length of men’s shorts are in style?

Most stylish men’s shorts fall 1-3 inches above your knee, which is a simple rule to follow. When picking the inseam of your shorts, you will typically want to keep it between 5 inches on the shorter side, and 9 inches on the longer side.

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