5 Expensive-Looking Shorts Outfits You Can Wear On Repeat
Not a dress or skirt person? Fear not, as shorts are a great option for your summer looks, and an be worn in a multitude of chic ways. Read on for your summer shorts inspo folder.


Emily Dawes
Shorts are undeniably one of the most worn fashion item over the summer months. It’s hardly surprising, though, when they not only keep you cool but also manage to look really polished. Not everyone is a dress person, and shorts provide a great alternative on those warm-weather days, and even worked layered up into autumn. The only problem is whereas a dress is an all-in-one instant outfit, shorts take a little more thinking about what to pair with them. If you can pin down a few easy combinations, though, they can be just as effortless to throw on in the morning.
So that you can skip the boring trial and error of putting together outfit combos, we've done the hard work for you and found five chic outfits to copy that'll see you through 99% of your summer calendar. Of course, there are a few co-ords involved because we all know shorts sets are having a serious moment right now. For smarter occasions, choose tailored shorts that you can add a classic blazer to for a polished finish. And for more relaxed affairs, like beach days and weekend wanderings, drawstring and denim options are your go-to.
No matter your style or the upcoming summer, you're bound to find an outfit you'll live in for the rest of the season. Keep scrolling to see and shop some of our favourite shorts looks to bookmark and replicate now.
1. LUNCH WITH FRIENDS
Style Notes: A trusty pair of blue denim shorts will never let you down. Opt for a long-line fit, which will make them great for running around the city, but still allowing you to feel covered up and agile, unlike a much shorter pair would. Pair with a classic black waistcoat and your most beloved sandals and sunnies for a casual, easy-going look. No fuss or over-accessorising required.
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2. BEACH STROLLS
Style Notes: There's something so effortless about a linen short, particularly when you can also invest in the matching shirt. Infinite combinations will ensue, which will keep you cool in the heat of the summer, whilst staying put-together and stylish. Perfect for holiday dressing—pair with flip-flops and a raffia tote.
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3. WEEKEND RELAXING
Style Notes: Boxer shorts have been on the rise (pun intended!) for a number of seasons now, and the fashion-conscious people of New York, Copenhagen and London have been spotted wearing them on the street, not just at home. Toughen them up with leather footwear and cozy, monochromatic styling. You just woke up like this!
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DMY Studios has a cult following, Kendall Jenner included.
4. DINNER IN THE CITY
Style Notes: Tailored shorts are a sure way to feel sleek and polished. Wearing all white may feel like a risky move in the city, but when pulled off, it can look infinitely classy. Pair silky white tailored shorts with a paper-weight tee or tank, with a creamy blazer and accessories for an intentionally timeless look.
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5. OFFICE-READY
Style Notes: When its hot in the city, how do you dress to stay cool but still office-appropriate? I'm taking notes from New York's Coco Schiffer, who effortlessly shows how to dress for desk days when the mercury is high. Wide, white shorts, paired with a crisp white shirt, boxy black blazer and chunky accessories, plus leather flip-flops, is the formula to choose.
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Sophie Robyn Watson is a London-based style editor with over 10 years of experience in the fashion, luxury and retail industries. She has worked at esteemed companies such as WGSN, ASOS, LFW, Alexander McQueen and GANNI. After graduating with a first-class honours degree in Fashion Promotion & Imaging, she moved into the luxury editorial sector with a focus on menswear, firstly at Wallpaper* and later Mr Porter, where she worked her way up from Fashion Assistant to become Fashion Editor. At Mr Porter, she worked on global marketing shoots, celebrity profiles and luxury shopping edits. In her role as Who What Wear UK’s Acting Fashion Editor, Sophie is chiefly interested in celebrating new and emerging brands that the cool-girls ought to know now.
- Emily DawesAffiliate Editor
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