The Chicest Women I Know Are Styling Shorts With These Timeless Shoe Trends This Summer
From soft leather loafers to knee-high boots, these seven shoe styles make long shorts look their chicest. Scroll to discover them.
After years of micro-shorts being top of the summer agenda, long shorts started quietly making their presence known last year. From Bermuda shorts to jorts and softly tailored culottes, each of these knee-grazing styles has been spotted in the spring/summer 2026 trend cycle. As the perfect transitional weather solution, their laid-back energy works remarkably well with the lightweight linens and billowing blouses that typically float our capsule wardrobes in summer. So, with the UK days away from a 25-degree spell, what better time to invest in warm-weather pieces than now? But, one question needs to be answered before we do: what shoes do we wear with long shorts in 2026?
Thankfully, fashion people are all too willing to provide us with plenty of inspo. Be it celebrity It girl Amelia Grey styling a pair of calf-skimming Adidas track pants with minimalist glove ballet flats, or Jennifer Lawrence in a three-piece ensemble finished with chic Mary Janes, as it turns out, even the "wrong shoe" works. Think sleek slingback pumps dressed up with lace-trimmed satin shorts, or vibrant tailoring finished with refined leather flip-flops. Almost every shoe works with these transitional heroes, but the seven styles below, in particular, make long shorts look their most stylish.
1. Pointed-Toe Heels
Style Notes: Though I was initially unsure if heels would work, this polished look from Ebony Aroha helped to change my mind. Bloomer shorts are inherently playful, but the classic, structured slingback adds an elegance that pairs well with the pretty lace trims.
Shop Pointed-Toe Heels:
These sleek kitten heels are so versatile.
We love a red shoe.
Ruching is having a major moment this summer.
Lately, I've been loving everything Calvin Klein is selling, shoes-wise.
The lace-up T-bar detail sets these apart.
2. Ballet Flats
Style Notes: One of this year's (and every year's) most-worn shoe styles, pretty ballet flats will soften any outfit. Leaning into the elegant nature of summer whites, Nnennae Chem uses her glove flats to ultra-polished effect.
Shop Ballet Flats:
They may not be the easiest to keep clean, but they're so pretty.
These have the classic gold triomphe emblem on the toe.
I've spotted quite a few pairs of icy-blue ballet flats around ahead of summer.
The dainty strap will make for comfortable all-day wear.
These also come in classic black.
3. Flip-Flops
Style Notes: Simple yet undeniably effective, the humble flip-flop has quickly become a fashion person’s favourite for one reason: its ease. Whilst the minimalist style allows you to show off your latest pedi, it's also so versatile that there’s yet to be a bottom that doesn’t pair well with a flip-flop. Personally, I’ll be taking cues from Marianne Smyth and styling mine with bright shorts and a fitted tank on warmer days this summer.
Shop Flip-Flops:
The look far more expensive than their £13 price tag.
From the contrasting colours to the square footbed, these flip-flops are utterly divine.
The gold embellishment is such a luxe-looking design detail.
These will work well with jeans, dresses and of course, your favourite linen two-piece.
Tkees is a brand to know in the summer shoe game.
4. Mules
Style Notes: Summer's favourite "ugly" shoe, the chunky mule, is a foolproof choice, especially if you're a pared-back dresser. The quietest way to make a statement with your shoes this season, this slip-on-and-go shoe balances breezy energy with all-day practicality. Plus, they make long jorts and oversized shirts feel far cooler.
Shop Mules:
Topshop's Addie mule-loafer hybrid looks great with everything from tailored trousers to jeans.
The soft cork footbed will provide you with endless comfort.
This khaki hue has been all over my social feeds lately.
From the elongated square toe to the delicate gold-finish metal bow, I think these might be Jonathan Anderson's best shoes of the season.
5. Loafers
Style Notes: Pairing well with jeans, dresses and maxi skirts, it's no surprise that loafers work well with long shorts too. With a distinctly preppy polish, pairing long Bermuda shorts with ruched loafers adds an edgier finish. Keeping the rest of her look practical, Millie Holmes layers a fiery red hoodie and denim jacket over a white T-shirt. It's an unexpected outfit, but it works.
Shop Loafers:
A Who What Wear UK editor favourite.
Style with white jorts and a vest top for a casual summery look.
Vagabond makes some of the comfiest loafers I own.
Iconic.
These are just so sleek.
6. Kitten-Heel Sandals
Style Notes: If you live for the summer months, you probably already own at least a few pairs of kitten-heel sandals. More secure than mesh flats or flip-flops, but dressier than a full shoe, the addition of a heel adds a chic edge. Take Marylin’s softly tailored culottes and funnel-neck windbreaker. Sure, the combo would look fine with trainers or ballet flats, but the heel makes it sleeker.
Shop Kitten-Heel Sandals:
A summer staple.
Style with a shirred dress and a raffia tote for drinks with friends on a warm day.
A pair that will never date.
This soft-brown hue is so rich-looking.
The teeny heel is super manageable, even for heel-phobes.
7. Boots
Style Notes: My personal favourite way to style long shorts has to be with a tall boot. There's something inherently cool about this high/low pairing, and whether you opt for fashion-forward biker boots or a knee-high style, this look isn't afraid to play with proportions. If Sofia Mcoelho’s combo of camo-print shorts and slouchy, suede boots is a touch eclectic for your taste, the pairing works just as well in classic colours and shapes.
Shop Boots:
A best-seller.
You can never go wrong with a classic, flat-soled biker style.
Not your average tall, black boots.
The perfect boho-style ankle boots.
These have gone straight into my basket.
