How To Style Shorts: A Guide For Guys

As we round the corner yet again into the hottest months of the year, shorts are on all of our minds.

They’re super comfortable and they allow for plenty of air to circulate.

Who doesn’t appreciate that?

Nonetheless, if you don’t know how to style them effectively, shorts can become the culprit of a major style blunder.

So, what is the best way to style shorts?

We’ve put together a guide for wearing shorts to give you a leg up in comfort without sacrificing style points.

Say goodbye to sweaty calves and wave hello to some newfound summer ensembles.

When You Should (And Shouldn’t) Wear Shorts

Before we can dive into some killer outfit ideas for shorts, it’s essential to cover the biggest question of all: when is it appropriate to wear shorts?

Because they’re often such a casual garment, it can be tough to know what the best occasions are to opt for shorts and when you should skip them altogether. 

Back in the olden days, shorts were considered a childish fashion choice for men—unless, of course, they were worn for swimming or sports.

Even today, plenty of people believe they shouldn’t be worn past childhood, let alone well into adulthood.

Fortunately, we aren’t those people.

Although we support your short-wearing adventures, it’s obvious to consider the occasion and respect all dress codes.

For example, if your office doesn’t allow shorts, it’s not an invitation to wear them.

We are adults, after all.

Regardless, here are a few basic guidelines to follow about when you should definitely leave them in the closet:

  • When an event is formal or semi-formal
  • Anytime you’re conducting business
  • If you’re unsure of the dress code and there’s a chance it’s not casual

However, for casual events and other occasions that are typically chill (i.e., you don’t have to impress anyone), shorts are generally a fine fashion choice.

For example, if you’re heading out for a stroll in the park with a date or you’re off to a Sunday afternoon barbecue, it’s probably safe to wear shorts. 

See Also: 12 Best Shoes To Wear With Shorts (For Men)

Selecting A Stylish Pair Of Shorts

More than merely buttoning them up around your waist, there is a way to wear shorts.

And it all begins with the style of shorts you opt for.

Believe it or not, there are shorts to reach for, and there are shorts to turn a blind eye to.

And the fit often makes or breaks the decision.

Let’s take a look at some of the obvious red flags:

  • Excessively baggy 
  • Overly tight
  • Too long (well past your knees)
  • Too short (the palest portion of your thighs is exposed)
  • Any kind of cargo shorts (for your sake)
  • Unnecessary dangly things hanging from the sides
  • Plaid

It’s advantageous to opt for shorts that have a five-to-seven-inch inseam and a flattering taper to them but aren’t tight enough to be a second skin.

You want to feel confident and comfortable in your shorts, so they should fit you well but allow for room to breathe.

To give you a solid head start in your shorts journey, some of the most classic and timeless short styles that seem to ebb and flow with fashion’s constantly changing atmosphere are chinos, denim cut-offs, jersey knit, and linen shorts.

Invest in these, and you’ll be sure to play the game right.  

See Also: Can You Wear A Flannel Shirt With Shorts?

How To Style Shorts

Now comes the tough part: deciding how to style your shorts.

Although we’ve covered two of the most essential concepts in shorts-wearing, the choice of clothing that you wear alongside your shorts has some of the biggest impacts on whether you’ll look like an icon or a flop.

But, surprisingly, shorts are far more versatile than most of us think.

You can dress them up or dress them down, but ensuring that your look is fashionable lies in your supplementary style choices.

That said, we’ve conjured up a list of five super-cool short outfit options that you can take for a spin as we make our way through the remaining summer months. 

So, without further ado, let’s get the ball rolling on some of our favorite fashion dos.

1. Keep it Cool & Casual

Shorts are casual themselves, so why not keep them in their element?

Playing it cool is an easy way to go about sporting shorts, and you can rarely go wrong with a simple ensemble.

Whether you’re heading to the beach or off to brunch, this look is a timeless one that’ll keep you looking sleek while staying cool—even on the warmest of afternoons. 

Chino shorts are a great pal in a casual moment, and they’re super easy to style.

Opt for a pair of khaki shorts—well fitted—that land about two or three inches above the knee.

Toss on a trusty sleek black tee-shirt and some black or white low-rise sneakers (some classic Vans are always a great choice).

Polish the look off with a black baseball cap and a pair of sunglasses. If you’re feeling wild, try adding a classy bracelet or watch, and you’re good to go. 

See Also: Are Cargo Shorts Out Of Style?

2. Strut Some Sporty Streetwear

It’s 2021, and the sports-luxe style is all the rage.

Not only is it a super comfortable way to keep up with the times, but keeping a sporty look is also especially practical.

Go from the grocery store to the court to play some ball, and then turn right back around and head to visit a friend.

You can’t go wrong with a streamlined athletic look—just ask Justin Bieber. 

Try a pair of charcoal cotton jersey lounge shorts that are about three inches above the knee.

Pair them with a beige tee-shirt, some white crew socks, and a pair of beige slides.

In cooler weather, toss on a light grey crew neck sweatshirt and hit the town.

If you’re on the hunt for less of a lounge look, try the shorts with a light grey graphic tee, and swap the slides out for a pair of hi-top sneakers.

Add a watch and some cool bracelets, and you’re ready to party—comfortably. 

3. Button it Up

The great thing about shorts is that you can essentially wear them with nearly any type of shirt, even a button-up.

If you’re hoping to try out a smart casual or preppy style with a pair of shorts, you’re in luck; it’s possible.

Here’s how to make it happen:

Step into a pair of navy or black chino shorts, and, of course, make sure they’re well-fitted.

In hot climates, button up a short-sleeved novelty button-up, and leave it untucked.

For more of a vintage look, opt for a flowy fabric and shoot for some white sneakers or matching brogues.

To keep things preppy, try a tighter fit and slip on a coordinating pair of boat shoes.

Don’t forget some classic sunglasses and a sleek watch, and you’re well on your way to making a welcoming statement. 

See Also: Can You Wear A Jacket With Shorts?

4. Go Monochrome

When in doubt, choose one color and run with it. Monochrome is the fashion look of the year, and for a good reason.

Keeping in-tone with an individual color is a great way to keep things simple, minimalistic, and fashionable.

However, if you’re new to the monochrome game, certain colors work best at a time like this—our favorites are khaki or beige, black, and grey. 

Choose a classy pair of black linen shorts—about four inches above the knee with an overlapping button flap—and tuck in a solid black, short-sleeved button-up.

Pair the look with some black leather loafers. Polish it off with a classy watch and some black sunglasses, and you’re good to go.

Or, for more of a casual ensemble, try a pair of light grey jersey knit shorts, a white, tall tee, and a matching grey crewneck sweatshirt.

Add some white crew socks and some low-top black sneakers.

Keep it cool with a black baseball cap or go hat-free and rock a fresh hairstyle. 

5. Dream of Denim 

When it comes to shorts, denim cutoffs are never the wrong choice.

From dark wash to white denim, jeans are cool.

Not to mention, they’re fit for most occasions and look great with nearly anything.

Here’s how to wear them:

Try a pair of distressed, dark-wash denim shorts.

Roll them up and allow them to land about two inches above your knees.

Toss on a classic grey tee-shirt and pair of colorful athleisure sneakers to top things off.

Or, go for some slim-fit, light-wash denim cutoffs, a white tee, and a plaid flannel, unbuttoned.

Roll your sleeves a few times and add a pair of low-top sneakers.

There you have it—the ideal summer fit.

Bottom Line

Men’s shorts have been a controversial topic in the fashion industry for decades.

Nonetheless, they can make the perfect easygoing bottoms, versatile enough to wear nearly anywhere.

From the beach to lunch, shorts are a functional, stylish choice that you can sport all over town.

Not to mention, they’re not too difficult to style.

Try one of our five outfit ideas on for size; you might never hide your calves again. 

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