The Chicest Women I Know Are Styling Shorts With These Timeless Shoes Trends This Summer
From soft leather loafers to knee-high boots, these seven shoe styles make long shorts look their chicest. Scroll to discover below.
After years of micro shorts being top of the summer agenda, long shorts have been quietly making their presence felt over the last few years. From Bermuda shorts to 'Jorts', and even a softly tailored culotte, each of these knee-grazing styles have been spotted in the spring/summer trend cycle for 2026. 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 wardrobe in summer. So, with the UK days way from a 30-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 fit' inspo. Be it celebrity It girl Amelia Grey styling a pair of calf-skimming Adidas track pants with a minimal glove ballet flat, or Jennifer Lawrence in a three piece ensemble finished with a chic Mary Jane—as it turns out, even the 'wrong shoe' works. Think sleek sling-back pumps dressed up with lace-trimmed satin shorts, or vibrant tailoring finished paired with refined leather flip-flops. Almost every shoe works with these transitional heroes, but these seven styles make long shorts look their most polished. Scroll to see and shop some of the chicest below.
1. Pointed-Toe Heels
Style Notes: Though I was initially unsure if a heel would work, this polished look from Ebony Aroha helped to change my mind. Bloomer shorts have an inherently playful silhouette, but the classic, structured slingback adds a timeless polish that pairs well with the prettier, romantic lace trims.
Shop Pointed-Toe Heels Below:
The sleek Kitten heel will provide your endless comfort.
Simple yet oh so sophisticated.
Ruching is having a major moment this summer.
I've been loving everything Calvin Klein is selling shoes wise.
The T-bar detail adds a pristine polish.
2. Ballet Flats
Style Notes: One of this year's (and every years) most worn shoe styles, pretty ballet flats add a classier finish to your standard summer rotation. Leaning into the elegant nature of summer whites, Nnennae Chem uses her glove flats to ultra-polished effect.
Shop Ballet Flats:
If you like these I'd be quick! So many sizes are selling out fast.
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 Mary Jane strap will make for comfortable wear all day.
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. While 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 a warmer day this summer.
Shop Flip-Flops:
The look far more expensive than their £13 price tag.
From the contrasting colour 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 fool-proof choice, especially if you're a pared-back dresser. The quietest way to make a loud statement, this slip-on-and-go shoe balances a breezy energy with all-day practicality. Plus, they make long jorts and tied oversized shirts feel far more considered.
Shop Clogs:
The Topshop Addie have quickly become a fashion favourite styled with everything from tailored trousers to jeans.
The soft cork footbed will provide you with endless comfort.
This soft, olive hue has been all over my social media feeds as of late.
From the elongated square toe to the delicate gold-finish metal bow the Baby Bow mule might just be Jonathan Anderson greatest shoe this 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, the pairing of long Bermudas with a ruched loafer adds an edgier finish. Keeping the rest of her look both practical and stylish, Millie Holmes layers a fiery red hoodie and denim jacket over a white t-shirt, an unexpected outfit but one which just works.
Shop Loafers:
A Who What Wear UK editors favourite.
Style with white jeans and a vest top for a casual look.
Vagabond make some of the comfiest loafers I own.
Iconic.
Kendall Jenner has a pair of minimal loafers almost identical to these.
6. Kitten Heel Sandals
Style Notes: If you’re living for summer months, kitten heel sandals is the one trend you need to know. More secure than a mesh flat or flip-flop, but dressier than a full shoe the addition of a heel adds a luxurious polish. Take Marylin’s softly tailored culottes and funnel-neck windbreaker. Sure, it would look fine with a trainer or ballet flat, but the heel adds a more directional spin that cannot be ignored.
Shop Kitten Heel Sandals:
A summer staple.
Style with a shirred dress and raffia tote when going to drinks with friends on a warm day.
A pair that will never date.
This soft brown hue is one of this years biggest colour trends.
7. Boots
Style Notes: My personal favourite way to style long shorts has to be with a tall boot. Theres something inherently cool about this high/low pairing, and whether you opt for a fashion-forward bikers or an elongating knee-high, 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 too.
Shop Boots:
A best seller.
You can never go wrong with a classic, flat-soled biker style.
I've seen these boots paired with long black shorts in London as of late.
The perfect Bohemian pair.
These have gone straight into my basket.
