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Can You Wear High Tops With Shorts? 6 Styling Suggestions

Can You Wear High Tops With Shorts? 6 Styling Suggestions

Who doesn’t love shorts?! They’re comfortable, easy to style, and always on-trend. They’re a wardrobe must-have whatever your style preferences might be. And, they’re easy to wear because they’re appropriate for pretty much any event you might be attending. But, can you wear high tops with shorts?

Now, there was a time when the answer to that question would have been a resounding “No!” Shorts were seen as too simple, too relaxed, and too informal. Designers, stylists, and fashionistas aplenty argued that a man (a modern gentleman, to be exact) should never wear shorts outside.

Shorts were deemed out of style by pretty much everyone whose opinion mattered. Over time, fashion became more and more forgiving and half-trousers (a.k.a. shorts) managed to return to the spotlight.

Shorts have been spotted on numerous runway shows, styled with Penny loafers (or even chunky ones), collared shirts, crewneck sweaters for the night, and simple tees and sneakers for the day.

Somehow, somewhere, shorts managed to become the new trousers that you can style whichever way you want. Follow the same rules you would with trousers and make sure you dress appropriately for the event rather than for the type of bottoms you’re wearing, and you’re guaranteed to look (and feel) your best.

But, can you wear high tops with shorts? What makes shorts and high tops such a controversial combination? What type of high tops works with shorts? Worry not, we’re bringing you a step-by-step guide on how to style these two pieces together – and get away with it!

Can you wear high tops with shorts?

Can You Wear High Tops With Shorts 6 Styling Suggestions

Yes, you can! High tops work great with shorts when you know how to style them appropriately. High tops and shorts can make you appear short and stubby when you choose the wrong style of the high tops or the wrong length of the shorts.

Jorts (really, really long shorts) have been trying to make a comeback, but they’re not the style of shorts you should go for when you’re planning on wearing your high tops. Now, high-top sneakers used to be reserved for the basketball court. But, they’ve evolved over the past couple of years.

Nowadays, high-top sneakers are made with every variation and modulation under the sun, from classic Nike Blazer mid-’77 vintage sneakers to avant-garde runway Rick Owens Geobasket sneakers. And, they’re worn pretty much everywhere but the basketball court.

Of course, there are a couple of rules you should follow when you’re trying to style these pieces together. First things first, high-top sneakers tend to look better with high-waisted shorts because they give off an elongated silhouette that’s generally desirable.

Other than that, you might want to go for fitted shorts for the same reason – but, that depends on the occasion. Sports shorts (or sunning shorts) that are looser and roomier look great with chunky high tops. Fitted, pleated, or flat-front shorts look better with Converse high tops or other classic styles.

How do you combine colors, though? As a general rule of thumb, you can’t go wrong with sticking to the same color palette, but playing with the shades.

Lighter-colored shorts need darker-colored high tops to create a color balance. Add a pop of color with accessories or accents on the upper part of your outfit and you’re good to go.

How can you wear high tops with shorts?

Google searching “can you wear high tops with shorts” means you’re probably thinking of an outfit while you’re typing the words.

Maybe you’re planning on going to a sports event and you’re thinking of wearing sports shorts with some style of high tops – but, you’re not sure which ones to go with.

Perhaps you’re going on a date with someone special and you’re thinking of wearing pleated shorts (fashion-forward thinking, right?) – but, you don’t know whether to go with Converse high tops or something a little more high-fashion.

Whatever the case might be, here are a couple of styling suggestions guaranteed to make your life a lot easier. Shorts and high tops might sound like a match made in hell, but they can be the fashion statement you need when you know how to style them the right way.

1. Running shorts

Running shorts are more fashionable than you might think! Running shorts used to be reserved for, well, running.

However, they’ve been circling the runway shows for a couple of years and they’ve resurfaced recently with the viral Fear of God Essentials running shorts. Now, how can you wear running shorts with high tops?

From what we have seen, most men have been styling them with knitted socks and slip-on sneakers or regular low-top sneakers. Running shorts are generally quite short which gives you enough room to play with footwear of different heights.

We would suggest going for something high-fashion such as the Aime Leon Dore x New Balance 650r high-top sneakers to stand out, or a play on classic running sneakers such as the Adidas Ultra Boost All Terrain high-top sneakers.

2. Cargo shorts

Nike Men's ACG Woven Belted Cargo Shorts (Large, Redstone/University Red)
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Cargo shorts don’t suck anymore! Turns out we’ve been hating on them for no freakin’ reason because cargo shorts are back and we couldn’t be happier.

To be completely honest, we weren’t the ones who ruined cargo shorts for everyone – everyone’s favorite bros named Chad or Xander were the ones who wore the ugliest, chunkiest, and bulkiest cargo shorts that made us hate them with a burning passion.

But, cargo shorts have since been trimmed down and turned into the stylish, streamlined staples they were always meant to be.

Nike ACG Snowgrass cargo shorts, Gramicci shell cargo shorts, and Adidas cargo shorts are pretty much the best cargo shorts you can go with and you can easily combine them with the high tops of your choice.

Cargo shorts are generally on the baggier side which means you should go for chunkier high tops to create balance.

3. Denim shorts

Oh, denim shorts are the easiest to style because they’re super, super versatile.

Whether you’re a fan of tight-fitting, denim shorts that don’t go past your thighs, baggier denim shorts, or even the dreaded jorts, there’s no reason why you wouldn’t be able to combine them with high tops (as long as you follow those rules we mentioned beforehand).

Wear them with simple tees and Converse Chuck 70 high-top sneakers or with denim button-downs (for a monochromatic, denim-on-denim vibe) and Puma Universal RDL high-top sneakers.

Give the outfit your signature style with accessories and details such as rolled-up sleeves or knitted socks. Denim shorts might not be appropriate for work or date nights, but they’re a streetwear staple for a reason.

4. Flat-front shorts

Dockers Men's Perfect Classic Fit 8" Shorts, Sea Cliff, 34
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Now we’re diving into the realm of shorts more appropriate for work and formal events. Shorts can definitely be formal, especially when we’re talking about flat-front shorts or pleated shorts.

When you wear them with loafers, cashmere sweaters, structured button-downs, and blazers, you have nothing to worry about.

But, can you wear high tops with shorts that look like they belong on the runway? You can, but you might have a hard time following the rules.

Combine flat-front shorts with a simple tee to take off some of that formal energy, throw on some earth-toned sneakers such as Madewell Court high-top sneakers, and make sure the rest of the outfit follows suit.

Or, go with the statement, high-fashion sneakers such as Saint Laurent Malibu leather high-top sneakers and a button-down for a more modern appearance.

5. Pleated shorts

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Pleated shorts are as tough to style as flat-front shorts, but “where there’s a will, there’s a way.” Pleated shorts are also more appropriate for the office, date night, and events where you want to look your best.

Pleated shorts combine well with simple tees and suede trench coats or button-downs and clean-cut blazers. High tops might not be the best choice of footwear, but you can make them work (depending on where you’re going).

Wear them with classic canvas high tops such as Converse Chuck 70 high top sneakers, leather high tops such as Fear of God Essentials high top sneakers, or avant-garde high tops such as Rick Owens Geobasket sneakers.

6. PJ shorts

Can You Wear High Tops With Shorts 6 Styling Suggestions

And no, we’re not talking about wearing PJ shorts and high tops to bed. PJ shorts (and other odd styles) have been circling for quite some time, with celebrities such as Bad Bunny, Kanye West, and Pharell Williams rocking them on a regular.

And, PJ shorts actually look pretty perfect when you know how to wear them appropriately – without looking like you rolled out of bed.

Wear them with a crushed bucket hat, rumpled Oxford-cloth shirt, and penny loafers. Better yet, wear them with tinted shades, a linen button-up, and fisherman sandals. Of course, you can also wear them with the high-fashion, avant-garde high tops we mentioned beforehand.

Dreams really do come true when you figure out you can wear PJ shorts outside without everyone thinking you’ve gone off the deep end. Whichever style you decide to go with, we’re keeping our fingers crossed that you look as great as you feel. Good luck!

Read this one: Shoes To Wear With Cargo Pants, For Both Men And Women

Can You Wear High Tops With Shorts 6 Styling Suggestions