13 Ways to Style Tailored Shorts for Smart Summer Dressing

We’re in the midst of a collective shift towards living in effortlessly elegant, understated, and timeless pieces. Tailoring has always and will always epitomize this style of dressing: Less is more, and during the sweltering summer months, this means gravitating towards staples that help you look put-together without heavy fabrics or a complex outfit formula. Tailored shorts hit a sweet summertime note—they’re smart and chic without being stifling, and they can be styled for literally any occasion. Ahead, see 13 ways to wear tailored shorts, from lounging around the house to attending semi-formal weddings—because this piece really can do it all.

For Sightseeing

Linen is a summertime savior: It looks crisp and clean, plus it's composed of longer, loosely woven fibers—so air can pass through and it’ll keep you cool. It wrinkles easily, but with linen, all is forgiven, making it ideal for travel. Wear a pair of breezy but structured linen shorts with a strapless linen top, ancient gold earrings, leather sandals, and a straw bucket bag.

For a Lunch Date

A sleeveless blouse gives hearty tweed a refreshing summer twist. Accessorize with a pair of mesh ballet flats—the texture will play well with the tweed, a lucite cuff, and a leather mini handbag.

For Cocktail Hour

For those who are hesitant to wear shorts, a long, slim-cut pair is a perfect first venture. Tuck a barely there camisole into the shorts, then slip a sheer mesh midi dress over both for a chic, unexpected ensemble. Mirror the early evening light with metallic sandals, a gold ring, and a strong, minimalist choker.

For the Office

When the thought of commuting to work in a pair of pants sounds like a punishment, trade in your tried-and-true trousers for tailored shorts. Pair a high-waisted style with a white button-down, neutral loafers, shimmery sheer socks, an olive-toned work bag, and a watch for a lighter take on the ultimate power suit.

For a Beach Day

Tailoring can work for a beach vacation with the right color palette: Light, watery shades will imbue the sharp cut with a welcome sense of breeziness. Pair baby blue shorts with a fished-from-the-ocean net tank worn over a neutral bandeau bikini top, floral jewelry, titanium sunglasses, and sand-toned sandals.

For Weekend Errands

Next time you have a few things to check off your list, run around town in an all-star look: pleated linen shorts, a sporty rugby shirt, fresh white sneakers, and a citrusy bag—all tied together with gold knot earrings.

For a Social Gathering

For a dressier daytime or semi-casual event, a bright shorts suit is a cool alternative to a cocktail dress. Wear a pair of ivory shorts with a gold or white silk top, a matching linen blazer, seashell pink kitten heels, a clutch, and a statement necklace.

For a Wedding

By mid-wedding season, we’re ready to jazz up our go-to rotation—and letting just an inch or two of a formal pair of tailored shorts peek out from underneath a glitzy dress is a great way to do so. Opt for a pair of shorter silk shorts in any shade but white, layered with a semi-sheer or super short dress and gold accessories.

For Gallery Hopping

It's hard to go wrong with head-to-toe black, and the key to making a dark monochrome ensemble sing is playing with a variety of different textures. Take in beautiful art in a pair of licorice black shorts, a pleated crepe top, square-toed flats, and a chic black bag—then throw in the slightest hint of color with a multicolored bangle.

For a Shopping Spree

There's a reason we often joke about shopping being one of our favorite workouts—it involves a lot of walking, shifting temperatures, and changing your outfit as you head from store to store to try on items. Slip on a pair of tailored shorts and an oversized button-down, and keep your accessories as un-fussy as possible (we like the idea of stud earrings, a headband, and a practical bag) so that you can focus on the demanding task at hand. This outfit will still feel fresh at the end of the day.

For a Day Off

There’s nothing more rejuvenating than doing literally nothing in a pair of boxers and a gigantic hand-me-down T-shirt. Elevate this sentiment in a pair of soft, slouchy tailored Bermuda shorts, an organic cotton tee, and house slides. If it’s chilly, Bermudas work beautifully with a faded hoodie.

For Date Night

Fill your date’s eyes with hearts in tailored leather shorts paired with a fitted, asymmetrical shirt, low-heeled sandals, tinsely earrings, and a sculpted gold cuff. This minimalist outfit is sure to work for whatever activities you may have planned during another summer of love.

For a House Party

Summer is filled with casual, at-home social events. Whether you’re hosting or attending, balance festive vibes with effortlessness in a mini dress that reveals the hem of a pair of textural, tailored shorts, an ocean-inspired necklace, and sandals you can slip on and off. Tie a cocoon cardigan around your shoulders to wear once the sun goes down.