How to Wear Shorts with Style (and Mistakes to Avoid)10 min read

What if I told you that shorts can be stylish, ultra versatile, dressed up or dressed down, and worn with a myriad of different types of shoes — would you believe me?

One of the reasons I started Gentleman Within is because my friends would ask me for style advice. I thought to myself, there’s got to be other style conscious men out there — why not share what I know.

So when a good friend from high school requested an article on how to wear shorts this summer and what type of shoes he should be wearing with them, I had to oblige. Dan, this one’s for you, and anyone else seeking advice on how to wear shorts with style this summer.

HOW TO WEAR SHORTS THIS SUMMER

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BE AWARE OF THESE SHORTS STYLE RULES

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First things first, I’m not advocating for ultra short shorts here. Nor am I on board with the long and baggy variety. Try to find shorts that are 1-3 inches above your knees. I like a good 2 inches as a general rule of thumb. As with jeans or pants, if your shorts are a bit long you can always cuff them up once or twice to achieve your desired length.

You also want to avoid a wide leg opening, unless you’re intentionally going for that look. It just looks sloppy. Aim for a more trim, tapered cut. It’ll look much more streamlined and clean. Trust me, it’s a better look for most men.

» Related: You might like this definitive guide to Summer Fabrics.

Avoid Wearing These Shorts In Public

Sure cargo shorts are functional, but that’s about the only thing going for them. Most cargo styles are baggy and look downright ugly. There’s a reason why they’re ruining marriages across America. All joking aside, it would benefit you to avoid committing this style sin.

Adam Sandler is notorious for wearing basketball shorts in public and it’s not a good look. See for yourself. Keep them where they belong—in a gym.

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LEARN FROM MY MISTAKES

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For whatever reason, the trend in the 90s, early 2000s was to wear shorts well past our knees. Here is an example of how not to wear shorts courtesy of my past self.

Early on in my style journey, I often wore shorts 3-4 inches too long, in this case they’re a good 6-8 inches longer than they should be. I was just following the trend at the time, and I sure hope that this doesn’t come back in style.

What’s wrong with this look?

1. The oversized linen button up
2. White on white on white
3. Neon green laces

I thought I knew what I was doing, but that shirt is too loose, too long and I’m too lucky it’s no longer in my wardrobe. The neon green shoelaces are obnoxiously loud. And the trendy shorts with frayed bottoms make me look even shorter than I already am. Avoid these mistakes at all costs.

STYLISH SHORTS OUTFITS

There are many types of shorts you can go with from chino shorts to denim shorts, linen shorts to sweat shorts, and printed shorts to swim shorts. That’s a lot of shorts!

Regardless of what kind of shorts you like to wear, there are endless ways to wear shorts this summer. And now, I’ll show you a 8 different ways.

» Quick Note: You might enjoy this best t-shirt brands roundup.

LOOK 1: THE SUMMER BRUNCH

For the first look on how to wear shorts this summer I’m styling shorts with a micro dot pattern, just to mix it up. If you can’t find a dotted pair, a solid gray works fine. The gray color makes it highly versatile.

This is the most casual of the first 3 looks. I’ve broken it into 3 separate outfits, swapping out the shirt in each one, taking into account the weather.

How to Wear Shorts with a V-Neck T-Shirt

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For the first of the three, I start things off with a basic v-neck t-shirt. This wardrobe staple will have you feeling comfortably cool all summer long. To continue with the casual vibe, I slip into a canvas sneaker in beige, matching the woven, cloth belt.

Tying together the fabrics and colors is the canvas strap watch. I finish off this casual getup with a pair of Ray Ban Clubmaster sunglasses for effortless cool. And since it’s summer, I like to throw minimal accessories into the mix for an added dash of style, in this case a thin leather bracelet.

How to Wear Shorts with a Lightweight Cotton Sweater

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If the weather calls for it, you can opt for a lightweight, textured sweater in place of a t-shirt that’ll give you the warmth you need while still looking casual cool.

How to Wear Shorts with a Chunky Knit Cardigan

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And in the case of those chilly summer mornings, remember to keep a thicker sweater like a chunky knit cardigan on deck, preferably in a neutral shade. Even better if it’s buttoned so you can treat it like a jacket. Whether you’re down with brunch or not, you’ll surely be brunching in style.

 

A post shared by Khoi N. | Gentleman Within (@thegentwithin) on Jun 10, 2017 at 3:12pm PDT

LOOK 2: THE SUMMER CLASSIC

Look two on how to wear shorts this summer is a classic for two reasons. First, navy and tan is a tried and true color pairing that looks good on a majority of men. Individually, they’re among the most versatile colors in menswear.

That’s the reason I gravitate towards this color scheme. Secondly, it doesn’t get more classic than a navy blazer paired with boat shoes.

How to Wear Shorts with a Navy Blazer

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This look is dressier due to the blazer and button up, but don’t be fooled, it’s still a relaxed, ‘I’m at play’ kind of look. It’s got preppy undertones and seems like something you’d wear on a boat, but I think it’s a look worth trying if you feel it would suit you.

One of my favorite aspects of this looks is the navy canvas belt by Anson Belt & Buckle. A canvas belt’s casual nature helps it to dress down the blazer and button up. It’s also the perfect belt for the summertime, providing a much needed break from the leather belts typically worn year round.

 

A post shared by Khoi N. | Gentleman Within (@thegentwithin) on Jun 11, 2017 at 7:19pm PDT

Details Worth Noting

Being a shorter guy (~5’6″) I’ve learned the benefit of wearing accessories. The red trim, linen pocket square with blue stripes is a fun detail that adds some visual interest to the outfit. I also added lapel pin for a pop of color.

It’s a conversational piece that I don’t mind talking about whenever people ask me where it’s from. It’s also worth noting that wearing accessories higher up on your body is also a good thing for shorter guys as it draws people’s attention upwards helping for you to appear taller. And yes, accessories aren’t just for the ladies.

As a man of details, I like to match my metals whenever I can. Though it’s not essential, it’s this extra attention to detail that can separate you from the rest. In this case, gun metal, matte finished belt buckle pairs well with the matte bezel of the watch face. 

Finally, if you want to experiment with a subtle printed shirt, go for a polka dot pattern in a neutral color. But since it’s summer, I say go wild with all kinds of fun prints.

Quick note: If you’re enjoying this post on how to wear shorts this summer, then you’ll probably find my other writing on all things men’s style useful. Each week, I share updates, style tips and other things not shared on the blog through my free email newsletter. To join now, just enter your email address below and click “Get Updates!”

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LOOK 3: THE SUMMER WEEKENDER

I like this look on how to wear shorts this summer particularly because it’s smart casual. If you’ve been following the blog for a while now, you know that I love to pair dressier pieces with more casual ones. This one features the navy chino short which has endless styling options.

Let’s start from the bottom up. The bit loafer shoes in a light brown (walnut) shade is one of my favorite colors for the summertime. The color is casual, the loafer is casual, but the metal ‘bit’ across the vamp makes it dressier than a regular penny loafer.

How to Wear Shorts with a Button Down Shirt

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Again, In addition to the color, I decided to match the metal of the belt buckle to the metal of the horse bit on the shoe. The watch is silver, but 2/3 is fine with me. Since it’s summer, let’s go with a beaded bracelet. You can wear these on the opposite wrist or the same wrist, depending on personal preference.

I threw in a red bandana pocket square for a pop of color, not to mention its function as a cloth to wipe my forehead in the summer heat. I also like how the red pocket square picks up the accent color from the watch strap. Details my friend.

How to Wear Shorts with a Denim Jacket

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If you want to, throw on the ever versatile denim jacket in a light or mid-wash to further dress down this look. It’s a classic that you can’t go wrong with. Rock it confidently with shorts and you’ll be stylin’ all weekend long.

Finally, I included a small pack of oil absorbing sheets since I always have oily skin, especially in the summertime. Super handy.

 

A post shared by Khoi N. | Gentleman Within (@thegentwithin) on Jun 12, 2017 at 3:16pm PDT

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LOOK 4: THE SUMMER BEACH BUM

For the final look, I wanted to create a outfit that’s ideal for those summer beach days, and then a second stylish look that will make for a seamless transition from the beach to the bar.

How to Wear Shorts with Flip Flops and Tank Top

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For your swim trunks, you can have fun. You’re at the beach, so no one’s going to be taking what you wear too seriously, unless you’re full on speedo, yikes. For this look, I went for navy swim trunks with white stripes. It’s minimal, but still visually interesting. For the beach, flip flops and tank tops are completely acceptable, in fact I recommend them.

Of course, you don’t want to forget other mandatories like your sunscreen with an SPF appropriate for your skin type and a face and body deodorizing wipe because with all the humid ocean air, it gets really sticky out there.

Finally, you’ll want to bring a large beach towel and some good reads. You’ll be beach bumming it like the best of ’em.

How to Wear Shorts with a Polo and Espadrilles

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For the second look on how to wear shorts this summer, everything’s the same with exception to the shirt and the shoes. In the case that you want to take things from the beach to the bar, you won’t have to completely change your look. You can simply swap your shirt and shoes.

Opt for a polo shirt over the tank top and espadrilles over the flip flops. They’ll elevate your beach look with little effort and still have you dressed appropriately for the location.

Keep your shades handy in case you need them, and don’t forget a casual bracelet which is perfect for summertime. I’m a fan of this beaded bracelet from The Dark Knot. It has a really good weight to it and the detailing is incredible.

 

A post shared by Khoi N. | Gentleman Within (@thegentwithin) on Jun 14, 2017 at 2:17pm PDT

WHAT SOCKS TO WEAR WITH SHORTS

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My advice is to opt for an invisible sock also known as no-show socks. This is one of those stylish guy secrets. Most of us aren’t barefooted in our shoes, that’s just plain old nasty and stinky too. If you get the right pair, they’re comfortable, keep your feet cool, and most importantly are not visible, so you’ll be nailing that sockless look.

Ever since I discovered the magic of no-show socks, I wear them all the time come summer, whether I’m rocking a low sneaker, a loafer or boat shoes.

You can also go for a low cut ankle sock for sneakers, but I prefer the no-show variety. And absolutely, no sky high socks, unless you’re vacationing in Bermuda or something.

IN THE END

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There you have it. I hope this styling editorial and accompanying video helped you see the many stylish ways to wear shorts this summer. See, you can do so much more than just the plain and simple shorts and t-shirt look.

This summer you’ll be ready to wear shorts dressed up, dressed down, and all over town, from the backyard to the beach. Happy Summer!

Which of these looks is your favorite?

Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.

Looking forward to seeing you in there.