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

They're so good, you'll buy every pair.

Street Style: September 20 - Milan Fashion Week Spring/Summer 2020
Edward BerthelotGetty Images

I have sworn by a high-waisted fit ever since I gave up low-rise jeans in high school. I love my high-waist Everlane black skinny jeans for winter and I love my Rag & Bone high-waist denim shorts 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.

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1 The Dressy-Casual Outfit
Clothing, White, Outerwear, Blazer, Suit, Pink, Jacket, Footwear, Fashion, Beige,
Design by Morgan McMullen

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, $61; 2. Le Specs sunglasses, $89; 3. Chanel earrings, $550; 4. Good American bodysuit, $119; 5. Isabel Marant shorts, $250; 6. Gray Matters slide, $498

2 The Weekend Outfit
Clothing, White, Black, Shorts, Footwear, Design, Illustration, Pattern, Sleeve, Pattern,
Design by Morgan McMullen

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, $169; 2. Quay sunglasses, $65; 3. H&M tank, $18; 4. Solid & Striped shorts, $198; 5. Isabel Marant tote, $140; 6. Gucci slides, $290

3 The Date-Night Outfit
White, Clothing, Brown, Shorts, Footwear, Fashion, Shoe, Beige, Jeans, Trousers,
Design by Morgan McMullen

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, $77; 2. Isabel Marant earrings, $90; 3. Ganni leather shorts, $445; 4. Brahmin bag, $345; 5. Sam Edelman sandals, $120

4 The Trendy Outfit
White, Clothing, Pink, Illustration, Footwear, Trousers, Crop top, Style,
Design by Morgan McMullen

Dive right into spring/summer 2020'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, $220; 2. Shashi necklace, $42 and Mejuri necklace, $235; 3. Lyndon Leone sunglasses, $60; 4. Remain shorts, $278; 5. Longchamp bag, $235; 6. Tod's sandals, $575

5 The Vacation Outfit
Clothing, White, Footwear, Sleeve, Outerwear, Shirt, Style,
Design by Morgan McMullen

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, $125; 2. Banana Republic sunglasses, $68; 3. Brixton hat, $33; 4. J.Crew bikini top, $19; 5. AGOLDE shorts, $128; 6. The Marc Jacobs tote, $195; 7. Dior sandals, $690

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