5 High-Waisted Short Outfit Ideas for When We Can Wear Them Again

I have sworn by a high-waisted fit ever since I gave up low-rise jeans in high school (opens in new tab). I love my high-waist Everlane black skinny jeans (opens in new tab) for winter and I love my Rag & Bone high-waist denim shorts  (opens in new tab)for summer, to name a few. For the most part, they're comfortable though I admit, when I eat to much the waistband does become a little tighter, but these are small sacrifices I make since the fit is so flattering. (Pro tip: look for a pair with a little stretch if you're worried about tightness). And let me tell you: There are so. many. good. high-waisted shorts available for spring/summer 2020. (My favorite is the leather style in outfit three, ahead.) Whether you're new to the high-waist game or searching for more ways to wear your favorite pair, here are five ways to style the slightly retro cut in a thoroughly modern way. By the end of summer, you'll be wondering why you ever wore anything else.

1.The Dressy-Casual Outfit 

For a dressy warm-weather option, style this pair of faded black denim shorts with a white bodysuit and a peach-colored blazer. A two-tone crisscross sandal and designer earrings give the ensemble a sophisticated and classy look, which works well if you plan to wear this into the office. You can easily take the look from work to happy hour by ditching the blazer and showing more skin. Slip on the sunglasses and toast with wine to the end of the work day as you watch the sun set on the rooftop with friends.

Shop the pieces: 1. Topshop blazer (opens in new tab), $61; 2. Le Specs sunglasses (opens in new tab), $89; 3. Chanel earrings (opens in new tab), $550; 4. Good American bodysuit (opens in new tab), $119; 5. Isabel Marant shorts (opens in new tab), $250; 6. Gray Matters slide (opens in new tab), $498

2.The Weekend Outfit 

It's the weekend and all of us are just trying to take it easy. This ensemble, then, hardly takes any effort to throw together since the base is versatile black linen shorts. Tuck your favorite tank into the bottoms and cover up with a printed short sleeve button-down (I like a good animal print) you can leave unbuttoned. Don't overthink your shoes: a pair of simple slides will do. The addition of an artsy canvas tote is great for carrying farmer's market finds.

Shop the pieces: 1. Faithfull the Brand shirt (opens in new tab), $169; 2. Quay sunglasses (opens in new tab), $65; 3. H&M tank (opens in new tab), $18; 4. Solid & Striped shorts (opens in new tab), $198; 5. Isabel Marant tote (opens in new tab), $140; 6. Gucci slides (opens in new tab), $290

3.The Date-Night Outfit

This high-waisted shorts outfit is date-night worthy, whether you're trying out a new restaurant or simply grabbing drinks with bae. First, there's the sexy off-the-shoulder button-down top to play up your collar bone and frame your face. Second, the wine-colored leather shorts give your outfit a special all-dressed-up-for-the occasion feel. Stick to a short heel sandal for that post-dinner stroll and break out a cute going-out handbag (leave that work tote at home!).

Shop the pieces: 1. Good American top (opens in new tab), $77; 2. Isabel Marant earrings (opens in new tab), $90; 3. Ganni leather shorts (opens in new tab), $445; 4. Brahmin bag (opens in new tab), $345; 5. Sam Edelman sandals (opens in new tab), $120

4.The Trendy Outfit 

Dive right into spring/summer 2020 (opens in new tab)'s biggest trends with a knit crop top and hot pink high-waisted Bermuda shorts (a real attention-getter). This outfit does show a bit of skin on top, making it easier for you to soak in that sun for a bronzed glow. If you feel a little too exposed, however, you can easily drape a light linen blazer over your shoulders or layer on a light cardigan. Accessorize with layered gold necklaces, a fun pair of sunnies, PVC sandals, and a mini bag for an outfit that'll make you look on-trend without feeling forced.

Shop the pieces: 1. Georgia Alice top (opens in new tab), $220; 2. Shashi necklace (opens in new tab), $42 and Mejuri necklace (opens in new tab), $235; 3. Lyndon Leone sunglasses (opens in new tab), $60; 4. Remain shorts (opens in new tab), $278; 5. Longchamp bag (opens in new tab), $235; 6. Tod's sandals (opens in new tab), $575

5.The Vacation Outfit 

Although any of these high-waisted shorts would work for vacation, a classic white pair provides endless mix-and-match options with tops and bikinis. Now's the time to break out your favorite designer resort accessories like this Marc Jacobs tote (it works as a catch-all for your inflight essentials and as a beach bag) and Dior slides that will pull double-duty as day-to-night sandals for the week. Don't forget to top off with a straw hat as you order yet another piña colada from the bar.

Shop the pieces: 1. Farm Rio blouse (opens in new tab), $125; 2. Banana Republic sunglasses (opens in new tab), $68; 3. Brixton hat (opens in new tab), $33; 4.  (opens in new tab)J.Crew bikini top (opens in new tab), $19; 5. AGOLDE shorts (opens in new tab), $128; 6. The Marc Jacobs tote (opens in new tab), $195; 7. Dior sandals (opens in new tab), $690