I've Worked It Out—These Are the 7 Best Shoes to Wear With Long Shorts
After so many months of paying our dues in thick, woolly layers, at last, the sun is rearing its head and 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 this year—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 on the up and honestly, I don't think that shorts have every looked chicer.
Still new on the scene, 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:
Mary janes are such an easy way to elevate your casual style.
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 linen composition makes these naturally breathable and ideal for hot summer days.
These dark red shoes are an easy way to add a pop of colour into your summer wardrobe.
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:
Wear with the matching waistcoat or style with a black top.
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:
The non-stretch denim shorts will take a little while to break in.
Slingback kitten heels are such an easy way to dress up your favourite jeans.
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:
This chocolate brown colour styles so well with blue and burgundy shades.
6. COWBOY BOOTS
Style Notes: Though we're well into the summer months now, 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 days.
SHOP LONG SHORTS AND COWBOY BOOTS:
I always come back to Agolde for the excellent denim items.
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, otherwise throw on a cotton shirt or boxy blazer to dress up your look.
SHOP LONG SHORTS AND TRAINERS:
These comfortable days are perfect for day-to-day use.
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.
-
Wait, Did Chanel Just Confirm That This Non-Flat, Non-Heel Shoe Trend Is No Longer Dated?
Margaret Qualley seems to think so.
By Allyson Payer
-
Sorry, Stilettos, But These '90s-Inspired, Prada-Coded Anti-Flats Are Hot on Your Trail
Consider me converted.
By Eliza Huber
-
The New Reformation Shorts Everyone Will Be Wearing This Summer
Plus, they are under $100.
By Michelle Scanga
-
Not Flats and Not Heels—This In-Between Shoe Trend Is Just Right for Spring 2025
It's comfortable too.
By Drew Elovitz
-
I Never Thought I'd Wear This Weird Sneaker Trend, But I Can't Stop Getting Compliments on It
They're kooky in the best, most Miu Miu way.
By Tara Gonzalez
-
In 2026, Fashion People in Paris and NYC Will Still Be Wearing This High-Net-Worth Shoe Trend
Timeless.
By Eliza Huber
-
The Pretty Shoe Trend Celebs Can't Stop Wearing on the Red Carpet in 2025
It's no coincidence.
By Allyson Payer
-
Elsa Hosk's Already Wearing 2025's First Viral Sneaker Trend
For $80? Say less.
By Eliza Huber