5 Expensive-Looking Shorts Outfits You Can Wear Again and Again

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. 


(Image credit: @emilyjdawes)

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 outfits to copy that'll see you through 99% of your summer calendar. Of course, there are a lot of 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 upcoming summer, you're bound to find and outfit you'll live in for the rest of the season. Keep scrolling to see and shop some of Instagram's favourite looks.

1. Dinner Date


(Image credit: @dawn.tan)

Style Notes: The waistcoat is still key, and the summer way to style it is with matching shorts. Add mules, statement earrings and sleek shades to make the coolest co-ord work for after-dark. 


2. Beach Strolls 


(Image credit: @aprillockhart)

Style Notes: There's something so effortless about a longline denim pair. Make like April and keep them relaxed with crochet, a cap and your trusty New Balance kicks. 


3. Office-Ready


(Image credit: @aidabadji_)

Style Notes: When you add an oversized blazer to shorter tailored shorts, you instantly make them more office-ready. Or, you could copy Aïda and go for a skort – yep, they're back!


4. Relaxing At the Weekend 


(Image credit: @monikh)

Style Notes: This Deiji Studios set has become a cult style, and for good reason. The linen set makes wearing PJs out of the house acceptable – what's not to approve of? Keep it classic and laidback with neutral fuss-free accessories.


5. Brunch With The Girls 


(Image credit: @charlottekuhrt)

Style Notes: The bandeau is back, and everyone is embracing the '90s favourite with open arms. Make it work for day by adding printed shorts and flatform sandals. You could always pack some heels in your bag in case you decide to stay out after brunch. 


Up Next: 8 Easy Summer Trouser Outfits I can't Wait to Copy

Emily Dawes
Affiliate Editor

Emily Dawes is the very definition of a fashion multi hyphenate. An editor, stylist and writer with over eleven years’ worth of experience in the industry, Emily is known for her impeccable taste, elegant outfit choices and being able to spot the next big thing in fashion from a mile off. Our readers loyally trust her advice and shopping suggestions; so much so she began her own column documenting the most expensive-looking pieces on the high street, which has become a top-performing piece of content for the Who What Wear brand.

Emily has worked for Who What Wear UK since 2020 in a myriad as roles, spanning from contributing editor and branded content editor. Now, she holds the position of affiliate editor and is responsible for the brand’s overall affiliate strategy, ideation and content execution. Working closely with Who What Wear UK’s affiliate manager, Emily has been instrumental in securing and nourishing brand partnerships, surpassing her goals as standard. Leading the team in tentpole shopping moments including Black Friday and Peak Trading, with Emily’s guidance and leadership, team Who What Wear is in a stronger affiliate position than ever before.

Prior to joining the Who What Wear team, Emily served as YOU Magazine’s acting fashion editor where she managed the fashion team and oversaw all fashion content output for the fast-paced weekly title. Emily is a stylist in her own right, having worked with a slew of VIP clients including writer and television personality, Elizabeth Day, as well as styling and art directing several celebrity cover shoots for glossy print publication, Grazia. Her adept fashion knowledge means brands regularly sought out to work with her as a consultant: previously she has developed marketing and content plans for brands for Cocoon and Edge of Ember. Before entering the industry, Emily obtained a Bachelor of Arts in English and American Studies with International Study from Nottingham University. Fun fact: Emily spent a year studying in America which saw her join a sorority during her time there.

When she’s not working or tracking down the chicest, new-in items to share with our audience, you’ll find Emily bestowing her East London home with her stylish flair, reading everything from the classics to cowboy romance novels and escaping to the country with husband, baby boy and dog, Roo, whenever she can.

Emily is currently on maternity leave.