Shorts are typically associated with casual outfits. Not to mention, with our country’s round-the-clock sweltering heat, it can even be deemed as part of one’s daily uniform, often worn during mundane activities like running errands, getting coffee, going to the grocery, or sneaking out at night to buy snacks at the convenience store. Shorts have always been our closest ally in comfort, but not so much in style.
With that in mind, it’s easy to dismiss the sartorial potential of a pair of shorts entirely. But the first step to broadening your fashion horizon is to acknowledge that there are plenty of silhouettes and fabrics to choose from, so you could pick out what best suits the occasion—yes, you can wear them to dressy affairs, too. Here, we show you some tricks and tips that prove just how stylish shorts can be.
Stylish Ways to Wear Shorts
1. Pair with a plain tee.
Putting on a simple T-shirt may be a no-brainer, but the devil is in the details: Make sure you add unexpected touches that you might have otherwise neglected, like a simple belt, a French-tucked shirt, or cuffing your sleeves a bit.
Here, a pair of pleated shorts is cinched with a belt that emphasizes the outfit’s hourglass shape. Choosing a simple black-and-white color combo is also a classic trick you can never go wrong with.
If your style is fun and playful, opt for shorts in cute pastel colors like this one in periwinkle and pair that with a relaxed white tee. Throw on those vintage sneakers and your favorite bucket hat, and you’re good to go.
For those with beachy style sensibilities, a.k.a. if you gravitate towards rustic touches and warm tones, you could take your paperbag-waisted shorts and tuck your white tee in to accentuate your curves. Complete the look with your favorite woven bag and sandals.
2. Pair with layered separates.
Layering isn’t reserved for cold climates. With a little creativity, you can pack on the pieces while staying cool amid our warm weather. The key is to choose light fabrics like cotton and linen, and to show skin in the right places so you always feel fresh.
For that Saturday brunch with friends, you can layer a camisole with a short-sleeved button-down that will give it a vintage touch. Wear with heels to lengthen your figure, or stick to comfy loafers for a classic look.
If you’re heading out to run some errands, why don’t you liven up your tank top and shorts with a fresh cotton button-down? Play with a blue-based color palette like this outfit comprised of faded denim cutoffs and a pin-striped button-down for a preppy look.
3. Go grunge.
Like a pair of black trousers, culottes, or a little black dress, jet black shorts can be worn in a myriad of ways. Take them for a spin on the streets by going for a cool grunge look—plus points if you’ve got a pair of cargo shorts to work with.
Add an interesting element to your look by playing with printed shirts to layer on top of your bralette or cropped top.
4. Cop a classic look with a crisp white button-down.
Next to the plain tee, perhaps the easiest way to dress up your well-loved denim shorts is to throw on a crisp white button-down. Not only does it instantly make you look polished, but it’s totally comfortable as well. Consider it your new weekend uniform.
Elevate your old denim shorts with a short-sleeved button-down and tie it at the waist for a flattering look. Got a full day ahead? Walk around the metro comfortably in white sneakers and add accessories with gold or silver hardware for a luxe touch.
As tempting as it is to tuck in your top, try something different: Just leave it as it is. It’ll appear “oversized” with your itty bitty cutoffs, which makes for an interesting look. Leave the collar open to subtly flaunt your decolletage.
5. Keep it simple in a button-down.
For a look that’s perfect for chill days, simply wear a colored short-sleeved button-down with your pleated shorts and tuck it in. Add a belt for good measure and a cute tote bag, too! Reminds you of those feel-good ‘80s movies, don’t you think?
6. Go for a monochromatic look.
If you can master the layering trick then this will be a breeze! Simply put together monochromatic pieces and feel free to mix in different fabrics to add texture. It’s a relaxed outfit that’s perfect for lounging around your friend’s apartment and watching Netflix all day.
7. Take the easy route by opting for coords.
Too lazy to comb through your wardrobe in search of matching separates? For a quick shortcut, cop coords instead and add accessories as you please—it’ll make you look more put-together.
8. Wear with a sweatshirt and heels.
Shorts aren’t just for hitting up the gym, and neither are your lumpy sweatshirts. Make it work with your trusty shorts by tucking it in and sealing it with a belt. What will make this ‘fit lean and mean though would be a sexy pair of heels and perhaps a little jewelry if you’re up for it.
9. Step it up with a sheer blouse.
Contrasting elements always make for an exciting look—it’s in the style handbook. For a tried and tested outfit, match your casual shorts with a fancy sheer top. Plus points if it comes with a cool neckline, like a mockneck or a pussybow collar. Feel free to add unexpected details like a cool bralette underneath!
10. Look sharp in a tailored blazer and heels
Blazers can instantly elevate any look, but they can make you look stiff instead of sharp when they aren’t balanced with the right pieces. For an on-point smart casual look, wear any pair of shorts with a tailored blazer. You can also opt for an oversized one for maximum impact.
You don’t have to stick to solid colors, too. In fact, this ensemble will be more refreshing when various prints and textures come into play, like Leandra Medine’s striped shirt, linen blazer, cotton shorts, and feathery heels!
If you think that adding a blazer to a perfectly casual outfit will make you look stingy than stylish, check out Kaia Gerber’s well-balanced look—it’s the sneakers and tiny leather handbag that did the trick.
11. Kick back and relax in linen separates.
Take that monochromatic look up a notch by including a blazer, and make it warm weather-friendly by choosing light fabrics like linen. You can even take this fresh outfit to the office if your dress code permits.
12. Look summer-ready in a printed blouse.
Fit right in with our tropical climate by flaunting fun printed pieces in warm tones. Eschew the typical flora and fauna for vintage prints instead—it will lend a classic touch to your ensemble that even your tita will approve of.
13. Stay sleek in a silk blouse.
For lazy days when you just want to throw on something and head out the door, might we suggest slipping into a silk blouse? It’s comfortable yet sophisticated enough to wear to a brunch with friends at the mall or to a family gathering. Up the ante by mixing accessories for an eclectic appeal—just pile them on and go.
14. Perfect the streetwear aesthetic with an oversized shirt and baggy shorts.
If you’re a #hypebae who prefers slouchy streetwear in favor of prim pieces, here’s the perfect style equation for you: Simply match your baggy shorts with an equally loose T-shirt for a boxy yet relaxed silhouette. Complete the look with sneakers or velcro sandals and the staple fanny pack.
15. Look like a ‘90s babe in a cropped cardigan or fuzzy top.
Caught the ‘90s fever? Cher Horowitz wouldn’t mind. Cop her cute, playful aesthetic by donning cuffed denim shorts with a cropped cardigan. Pair with vintage-looking chunky sneakers and dainty accessories.
16. Relive your childhood in candy-hued separates.
Feeling nostalgic? Drape yourself in the wardrobe staples of your youth with striped camisoles, candy necklaces, and colored shorts paired with white socks. Butterfly accessories, optional.