How To Wear 10 Types Of Shorts

It’s hard to think of one piece of everyday clothing more casual than a pair of shorts (barring your bathrobe, of course), which is why you only seem to wear shorts when you’re really slumming it. Sure, shorts might be your go-to when it comes to cleaning out your garage or playing catch with your pup, but the most “styling” that goes into your shorts game seems to be making sure that the accompanying T-shirt is clean. It doesn’t have to be that way. 

In our opinion, shorts are one of the most flattering, fashion-forward, and — yes — practical pieces in your summer wardrobe and can come across as more sophisticated than schlubby. Need proof? We’ve highlighted 10 shorts styles we’re loving this season and shared the styling tips that’ll make your legs sing.

1

Cutoffs — A good pair of ripped, torn, frayed denim is probably one of the most flattering things you could wear. A bad pair though? Oof — only on moving day. If you want to wear them in real life, we love the look of balancing it out with a beautiful, fuller blouse and high platforms with a thick heel. 

Zara Ripped Shorts, $59.90, available at Zara

2

Culottes — With a high waist, long length, and wide legs, the culottes are the giants of the shorts family. Wear them with stilettos and a crop top to keep things looking trim. 

Topshop Tailored Culottes, $76, available at Topshop

3

High-Waisted Shorts — Since high-waist shorts take up quite a bit of visual space, use that opportunity to really go bold with your colors and simple with the silhouette. Shell-tank-style tops in a bold hue tuck in really nicely with graphic-printed shorts. 

ASOS Shorts, $50.91, available at ASOS

4

Lace Shorts — Avoid syrupy-sweet items when wearing lace shorts. Tomboy basics like lightweight sweats, loafers, and satchels balance out the lace perfectly! If your lace shorts are on the flimsier side, avoid tucking things into them. 

DKNY Scalloped Hem Shorts, $306.62, available at My Wardrobe

5

Bermuda Shorts — It’s easy to look like you’re a camp counselor in Bermuda shorts and a T-shirt, so always opt for delicate tanks that show off some skin. Pretty jewelry, flowery prints, and a chunky heel will help you look like a Parisian, not a Paris tourist. 

Photo: Courtesy of Madewell

6

Baggy Shorts — When it comes to cargo styles, flowing cotton, or baggy linen shorts, it can seem instinctual to want to tuck in a slim-fit tank. That’s all fine and swell, but we challenge you to wear it with a boxier top as well. Two more voluminous styles might seem like it’d drown you out, but the key is to make sure the proportions are right — you’ll want the shorts to end just above your fingertips and the sleeves and neckline to be cut low. A strappy pair of sandals will keep things from looking too heavy. 

H&M Lyocell Shorts, $32.95, available at H&M

7

Skirt Shorts — Skorts, despite having a dowdy reputation, are oftentimes cut much shorter than you’d dare to wear a skirt (and look that way to other people, too!). Wear a more covered-up top to keep things from looking too R-rated. Since you’ll be showing quite a bit of leg, wear them with heels with an ankle strap or a pair of cute flats. 

Mango Pleated Skirt Shorts, $34.99, available at Mango

8

Leather Shorts — Leather shorts are a tricky beast to navigate (because, let’s be honest, you can really only wear it when it’s a perfect 75 degrees out). For daytime, we like to wear ours with a paper-thin T-shirt and no-fuss flats. For nighttime, we break out our platforms and tuck in a silky camisole. 

Lot78 Leather Shorts, $580, available at Net-a-Porter

9

Track Shorts — A couple seasons old, track shorts are still a strong trend, but we like them this summer without the overt athletic references. Wear your pair with a button-up shirt in a contrasting print (pro tip: If your shorts are thick enough, tuck in the top for a more buttoned-up look!). As for your shoes, wear a gladiator sandal or oxford flat — no need to go too high or too flimsy! 

Pixie Market Grid Shorts, $75, available at PIxie Market

10

Pajama Shorts — An all-over print in a lightweight fabric can seem too casual for anything but couch lounging, but it’s not so if you wear it with a structured jacket and a lower heel. If your jacket matches the shorts? Even better! 

Photo: Courtesy of Zara

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