After 15 Years, I Finally Feel Confident Wearing Shorts (and You Can Too)

What we wear can have a direct impact on how we feel about ourselves. For example, when I find a garment that makes me feel confident, I’ll buy it in every colour-way possible. If that’s not an option, I have been known to invest in an identical backup option before I’ve had my sartorial fill of the original piece. An ASOS bikini comes to mind, as does a pair of Mango jeans that fit me just so. These are items I find myself turning to again and again when I need to feel good about myself—be it on the beach or on a night out with friends. When I put on that ASOS bikini, I feel like Beyoncé—and that’s exactly how your clothes should make you feel too.


(Image credit: @monikh)

However, I’d be lying if I said I feel 100% confident in all clothing. In fact, there’s one item I’ve been doing my best to avoid: shorts. There was no tipping point; no one ever said I didn’t look good in them. I’ve certainly worm dresses shorter than traditional pairs, so I know the length is not the issue. I’ve always been curvy and just felt that they didn’t do my frame justice. As such, I never really tried them. That was, until last summer.


(Image credit: @nnennaechem)

Call it frock fatigue, but when it was too hot to wear trousers, I set about finding a pair of shorts I could wear with pride. I tried on every style you can think of (cycling, Bermuda, tailored, floaty, you name it) and eventually, I started to see a pattern. Every pair that I liked had a paper-bag or belted waist. With a fitted top tucked in, my confidence levels were off the charts.


(Image credit: @wethepeoplestyle)

Now, I know many of you will have the same reservations that I used to harbour, which is why I’ve decided to break down the best shorts for your body type. As far as I’m concerned, anyone can wear whatever the hell they want to as long as it makes them feel good, and that’s my intent: to make you feel good about wearing shorts. Below you’ll find the top shorts trends of the season, as well as harder pointers on how to wear them with maximum confidence. Bare-leg season is coming, and I’ve got you covered.


A welcome change from the tailored skirts you usually wear to the office, longline tailored shorts—also known as city shorts—will make you feel on top of your game in the workplace and will be the envy of all your fashionably minded colleagues (just wear them with a crisp shirt and structured blazer). Heels are a viable shoe option thanks to the longer hem of city shorts, so wear them if you please.

Paper Bag

Now, we come to my personal favourite: paperbag-waist shorts. For me, they follow the outline of my curvy shape, but you can wear them regardless of your body type. Monikh Dale takes advantage of the higher waistline by wearing it with a crop top (if the waistband was lower, it wouldn’t look quite as chic).

Related: Summer 2019 Fashion Trends: Looks You Need to Know


Usually made of more hardwearing fabrics like thick cotton, utility shorts are easily the most practical of the bunch. They’re simple to style, too. Keep your shoes flat and your tops tucked in to show off those statement pockets.


Bloomer shorts are a cutesy way to channel the trend. The ruffle details—whether they’re all over or on the hem—mean that you should keep the rest of your look pared-back, allowing your shorts to be the statement piece. A linen blouse with a couple of buttons left undone will do the trick. As for your feet, keep things simple with a pair of tan or black leather slide sandals.

Related: Trust Me—These Under-£50 Pieces Look So Much More Expensive

Box Pleat

Thanks to the large pleat at the front of each leg, these shorts tend to be baggier and comfier than most. The sleek silhouette presents the opportunity to wear them with a more flamboyant top (perhaps an off-the-shoulder style). I suggest keeping it tucked in, though, in order to show off the chic pleat detailing.


There’s no denying that cycling shorts are a tricky piece to style, but after extensive research, I’ve found they look their best with a slim-fit blazer or worn underneath an oversized shirt for the perfect fit balance. As for the shoes, play on the retro vibe with a pair of "dad” trainers or velcro-strap sandals. 

Now that you’ve found your short soulmate, take a look at the sandals to go with

Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over thirteen years of experience in fashion journalism. She been creating engaging and elevated style content specifically for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, leads the editorial team in their SEO strategy and keyword planning, works closely with the beauty team on content initiatives, represents the brand at industry events, and regularly contributes to social media, including her own Who What Wear UK TikTok franchise, French Style Fridays. Previously, Maxine appeared on ITV's This Morning in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o.

Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship at Look magazine, she was offered a position on the brand's fashion desk. She accepted, leaving university a year early in the process. Her passion and natural talent for writing and styling meant she swiftly rose through the ranks to become the title's fashion news and commercial content editor, with a stint as’s fashion and beauty writer along the way. She later served as Look’s acting Editor in Chief, overseeing both print and digital, before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others.

Maxine is based remotely from her countryside home near Edinburgh where she spends her downtime renovating her house, walking her dogs, hosting friends and trying to master the art of making Old Fashioned cocktails.