Ava Gilchrist
As someone who has always relied on summer dresses to get me through warm weather, shorts haven't featured much in my wardrobe until very recently. Sure, The Frankie Shop's Boxers might've been the pair to convince me, but now that I'm totally sold on a bare-legged summer filled with chic short outfits, I've found it difficult to know how to style my new additions.
Well, that's at least the case where footwear are concerned. Often, the outfit is complete when I pair the thigh-grazing bottoms with an elegant top like a button-down, tank top, sweatshirt or blouse. But as soon as it comes to summer shoes, it's difficult to keep the momentum going. Are trainers too casual to wear with shorts and a blazer? Are loafers too polished for a sweatshirt and shorts outfit? However, as someone who adores shoes almost as much as I now do shorts, I decided to go in search of some inspiration that would breathe new life into the styles that I already have at home to make summer outfit building a breeze.
The thing I found most challenging about finding the right shoes to wear with shorts is getting the balance of proportions right. Tiny micro-shorts can be leg-lengthening with the right shoe but can often feel too naked. And, whilst long shorts are currently enjoying a revival, any shoe that cuts you off at the calf is only going to make you look shorter.
With all of this in mind, I set about conducting some lengthy try-on sessions and lots of social scrolling to come up with six shoe and shorts combinations that have the fashion-editor stamp of approval. Keep scrolling to see and shop the shorts and shoe formulas that I'm confident you will agree really are the best.
The Best Shoes to Wear With Shorts
1. Flip-Flops
Style Notes: Hurrah for sandal season! It only really comes around once a year (and the window for flip-flops is even smaller), so now that the sun is ready to make a regular appearance, schedule your pedicure in preparation for a chic shorts and flip-flops outfit as modelled above. Whether you opt for a casual white t-shirt, shorts and jelly shoes or dress up a tailored pair with a thong sandal, there's nothing better than this minimalist shoe on a particularly hot day.
Shop the Shorts:
I'm surprised these haven't already sold out.
Such a cool denim wash.
Yes, you read that price correctly.
Shop Flip-Flops:
Forget about The Row's Dune flip flops, the Ancient Greek Sandal Saionara Jelly flip flops are the shoe of the summer.
The editor and influencer shoe of choice.
An all-white outfit I can get behind.
2. Trainers
Style Notes: The sportier ones amongst you will already be familiar with this age-old combination, as the shorts and trainer pairing will already be in your gym bag. Don't keep this look just for exercising though—it works just as easily for a busy weekend or brunch with friends. Just pair bright shorts with a pair of trainers that are in fashion and keep a jumper to hand for tying around your shoulders (just in case). This look is versatile enough to take you from the great outdoors to lounging at home, so it's well worth re-creating as part of your off-duty uniform.
Shop the Shorts:
This cute shade of yellow makes me feel happier just by looking at it.
Lets not forget how chic gingham can be, either!
Thanks to a Loewe collab, everyone is wearing On training gear right now. I especially love this powder pink colour
Shop Trainers:
The Adidas Taekwondos are coming for the Sambas crown.
The classic choice for denim and dresses.
This baby blue suede has me hooked.
3. Ballet Flats
Style Notes: Trust Scandi Anouk Vye to style a French classic like the ballet pump with such European effortlessness. I'm just happy to back any flat-shoe trend, which means I don't have to compromise on comfort to get the desired look, and this outfit is a masterclass in how the right shoe can elevate an entire ensemble.
Shop the Shorts:
Sand-coloured shorts still feel dressy enough for the office when styled with a crisp white shirt and heeled summer work shoes.
These are going to be so popular in high summer.
This entire look is proof of the versatility of neutral shorts. (Yes, olive greens and khakis are neutrals.)
Shop the Ballet Flats:
How to up the cool factor.
If you don't know by now, suede ballet flats are the seasonal way to try the timeless footwear style. I'd happily take a pair of these in every colour. (All five of them!)
Clean, sleek and simple.
4. Strappy Sandals
Style Notes: There's no need to reinvent the wheel when strappy sandals and shorts look this good together. Honestly, this elegant combo needs no explanation, but I find it looks best when a pair of light and breezy linen shorts are put with a structured, minimalist sandal in brown, black or even red. Take tips from Emily Wells (pictured above) and double up on the linen for a heatwave-ready outfit that spares you the fuss.
Shop the Shorts:
The perfect cut.
Not into white linen? How about a paperbag style with textured frayed detailing?
Or, a gorgeous rust-hue pair with delicate embroidery from fashion's perennial favourite quiet luxury brand, Loro Piana?
Shop Flat Sandals:
I've been in love with the A.Emery Jalen sandals since I first saw them—as with nearly every fashion insider and in-the-know influencer.
Bravo, Reformation. I immediately want to buy this toe-ring style.
The dressy snake print really elevates the simple shape of this Khaite pair.
5. Block Heels
Style Notes: Not everyone is a flat-shoe fan, so heel-wearers, this one's for you! Save yourself from tottering around in a mismatched stiletto and shorts combo by opting for a chunky block heel instead. You'll still get the height (and make your legs look impossibly long) without having to suffer for a skinny heel. Wearability is key in summer when the weather is far too hot to deal with extra faff, so take a load off with a dressy shoe that does all the hard work for you.
Shop the Shorts:
Every person I know has these lace-trimmed Dôen satin shorts on their wishlist.
Another pair I'd love to cruise around in during summertime.
Clever pleats add structure to an otherwise plain pair of shorts.
Shop Block Heels:
& Other Stories brings this style back year after year in slightly different guises.
Tan, black or green. You decide.
The ruching on this style is so elegant.
6. Kitten Heels
Style Notes: Another negligible heel option for pairing with shorts, kitten heels add a lengthening effect to your look, which complements the cropped hemline of summer bottoms. What I love most about kitten heels is that you don't ever have to think about whether they'll complement your short outfits. Irrespective of where the hemline of your shorts fall, the minuscule heel adds an element of sophistication to exposed legs.
Shop the Shorts:
The shape of this pair is so expensive-looking.
The studs on this pair is Parisian-approved.
Make it summer-appropriate with this cream leather.
Shop Kitten Heels:
A kitten heel flip-flop is arguably the most sensual summer sandal—just ask Carrie Bradshaw!
How luxe is this red?
Pair with denim shorts and a pendant cord necklace.
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This Sandal Colour Is Chic, Goes With Everything and Is the Perfect Alternative to BlackEnduringly cool.
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The Casual and Elegant Trouser Trend Fashion People Everywhere Are Wearing With Flats and TrainersWear it for the gym, brunch or errands.
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I Worried This Sandal Trend Might Be "Out", But This Expensive-Looking Update Just Saved ItI'm hooked.
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Shelve Your Heels—These Are the 5 Flat-Shoe Trends That Will Define Summer 2025Only comfortable pairs need apply.
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It's Legs-Out Season—These 9 Shorts Trends Come Fashion-Person ApprovedKeeping things brief.
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As Seen in New York: A Surprisingly Chic Way to Wear Culottes (Yes, I Said Culottes) This SummerI feel a trend catching on.
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This Jeans and Sandal Formula is the Key to Looking Polished All SummerI'm convinced.
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I Thought Flip-Flops Looked Scruffy—This Trending Style Completely Changed My MindI'm recommending them to all my friends.
