For the past year or so, I've been scrolling past images of stylish people in long, knee-grazing shorts, quickly filing them under: Trends I Can’t Pull Off. Those tailored Bermuda styles and elongated denim cut-offs always look cool on Instagram, paired with crisp button-downs and structured blazers, but something deep inside told me it would look all wrong if I translated it to real life.
However, I'm not one to shy away from a challenge. After mulling it over (and saving a few inspiration shots that didn't feel completely out of reach), I realised that part of what was putting me off wasn’t the shorts themselves. The problem was that none of my go-to shoes seemed to work with the silhouette. Sneakers felt too laid-back for my personal style, flat sandals didn’t do much for proportion, but heels? Suddenly, I was onto something.
If your style leans more feminine like mine, the right pair of heels is all it takes to make long shorts work effortlessly with the rest of your wardrobe. I’m not talking about sky-high stilettos—just a bit of lift can completely transform the look. That added height brings balance to the relaxed silhouette and instantly makes the outfit feel more polished and put-together.
See for yourself—below, I've rounded up the best heels to wear with long shorts, from simple kitten heels to strappy sandals.
The Best Shoes to Wear With Long Shorts:
1. Kitten Heel Slingbacks
Style Notes: Everything looks more expensive paired with a kitten heel. Annabel's tailored black shorts, heather grey T-shirt and slingbacks outfit is exactly the kind of high-low dressing I'm aiming for this summer.
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A wear-with-everything pair.
These could also be fun with jorts for an unexpected double denim moment.
I love these styled simply with a white tee.
The perfect summer netural.
2. Chunky Wedges
Style Notes: Whether wedges can be considered heels is up for debate (they add height, don't they?) but either way, I think they successfully add a dressy touch to long shorts outfits without feeling like too strong a contrast.
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Safari chic.
All the nineties vibes.
The boxer shorts trend meets the long shorts trend.
These might be high, but they're super comfortable.
3. Minimal Pumps
Style Notes: When I find myself in the midst of a fashion conundrum, I remind myself that I always feel better in simple, trusted formulas over adventurous combinations. Enter the minimal pump—my saving grace when I can't decide on a shoe option.
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In 2025, shorts like these are a summer staple.
I've had these on my wish list for years—I might finally cave.
This feels like a very grown-up pair.
Year-round pumps.
4. Pointed Heels
Style Notes: The contrast here is so fun. Pointed heels feel refined and elegant, two qualities which will give the boyish shorts a more considered feel. Add a rugby-style polo, like Grace, to really lean into the juxtaposition.
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These shorts with a chocolate brown tee? Perfection.
Icons.
The butter yellow shorts of my dreams.
Wear these with tailored bermuda shorts for days in the office.
5. Heeled Flip-Flops
Style Notes: This one might be a cheat, because really, aren't we all living in flip-flops now that the weather has picked up? They're a fail-safe style for a reason, and they look just as good with elongated shorts as everything else in your wardrobe. A little heel just elevates the entire look.
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I love the idea of wearing these with flat sandals too.
These double as a great wedding guest shoe.
So incredibly chic.
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