I've Worked It Out—These Are the 7 Best Shoes to Wear With Long Shorts
Long shorts have cemented themselves as a summer capsule wardrobe staple, but what shoes look best with them? No need to worry, as below I've outlined the best shoes to wear with long shots, from flats to heels, and everything in between.


Katie Sims
By this point in the year, the thick, woolly layers of winter feel like a distant memory and now that the sun is regularly rearing its head, it's time to celebrate in the only way we know how—through clothing.
Excitingly for us there are some fresh summer trends entering the rotation in 2025—including my new favourite trouser trend: long shorts. A pallet cleanser to the micro shorts that have dominated fashion crowds and runways for so long, this season, the laid-back long shorts trend is finally on the up and honestly, I don't think that shorts have every looked chicer.
Long shorts started to appear on our fashion feeds late last summer and so they're still fairly new to our wardrobes. As such, I've rounded up seven of the chicest shoe pairings that always look good with long shorts, in order to give you a head start on styling the trend. Read on to discover the seven best shoes to wear with long shorts below.
DISCOVER THE CHICEST SHOES AND LONG SHORTS PAIRINGS HERE:
1. MARY JANES
Style Notes: Adding a pretty and feminine edge to your daily styling, the mary jane shoe trend is a summer wardrobe staple. Giving the relaxed shorts a smarter edge, this clever combination makes for an elegant outfit that you can style throughout the working week and beyond.
SHOP LONG SHORTS AND MARY JANES:
2. BALLET FLATS
Style Notes: I'll always come back to ballet flats when I want to inject a classy edge. Leaning in to the elegant nature of the longer hemline, ballet flats and long shorts work together to give your outfit an ultra-polished energy.
SHOP LONG SHORTS AND BALLET FLATS:
The butter yellow colour trend is taking off this season.
3. THONG SANDALS
Style Notes: Lightweight, casual and perfect for hot summer days, thong sandals are the trending shoe silhouette that you can catch me in all summer long. Wear with long-line shorts for a breezy weekend look, and dress your style up with a boxy blazer or button down.
SHOP LONG SHORTS AND THONG SANDALS:
I'm picturing these with many summer outfits, from day to night.
Easily the most comfortable flip flops on the market.
4. SLINGBACKS
Style Notes: Slingback shoes are one of my favourite footwear trends of the year. Classy, comfortable, and so very elegant, the sleek silhouette delivers a graceful look every time. To style an outfit that feels both trendy and timeless, pair your favourite slingbacks with longline denim shorts and style with a white tee or shirt.
SHOP LONG SHORTS AND SLINGBACKS:
5. CAGED SHOES
Style Notes: If you're living out the summer months in a city, then the caged sandal trend is the one you need to know. More protective that a strappy sandal or mesh flat, these chunky shoes ensure a comfortable stride and a chic silhouette. Wear with long denim shorts for an easy ensemble you can feel comfortable in all day long.
SHOP LONG SHORTS AND CAGED SHOES:
6. COWBOY BOOTS
Style Notes: The summer months might be inching closer, but the cowboy boots trend continues to thrive. Styling so well with long cotton and denim shorts, the easy combination will keep you comfortable and cosy on those cooler summer nights.
SHOP LONG SHORTS AND COWBOY BOOTS:
7. TRAINERS
Style Notes: Sporty shorts and chunky trainers are the unsung hero of my weekend wardrobe. Lean in to the comfortable energy and style with a roomy jumper on chillier days, otherwise throw on a cotton shirt or boxy blazer to dress up your look.
SHOP LONG SHORTS AND TRAINERS:

Natalie Munro is Who What Wear UK’s news writer and has worked in the fashion industry since she graduated with a degree in Journalism from the University of the Arts London. Natalie’s experience in the industry spans journalistic and styling roles that have seen her work for publications including British Vogue, Conde Nast Traveller, Vogue Ukraine, AnOther Magazine and Elle UK.
With an interest in uncovering the latest fashion trends, Natalie takes a leading role in identifying news for Who What Wear UK. Reporting on a daily basis, Natalie focuses on trends on and off the runway, as well as street style and celebrity fashion. Natalie also creates content for Who What Wear’s social channels including TikTok and Instagram on a weekly basis.
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