I’m a Stylist Over 40—These Are the 6 Shorts Styles I Wear on Repeat
Words by Jessica
There’s a moment every summer when the heat finally tips over and shorts become the only thing I want to wear. It took me a while to get here in all honesty, I was never all that keen on my legs, but this year I thought, sod it: life’s too short and it’s far too hot not to wear them. But if you’ve ever feeling hesitated over shorts, especially past 40, I promise the right pair changes everything.
Because styling shorts isn’t about your age, or legs, or any of the things we tell ourselves, they’re about cut, length and fabric, and finding the styles that genuinely make you feel good. So I’ve whittled my own collection down to six I now wear on repeat, each earning its place for a different reason. Here’s how I wear every one, and the little details that make them work.
Denim shorts
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Denim shorts are where I always start. For me, the length is everything: I like them to sit just about where my thigh curves in — it’s the most flattering cut, and the point where they feel effortless rather than too mumsy. If you’re struggling to find that perfect length, simply size up. I actually love the way denim ruches when you cinch it in with a belt, so a slightly roomier pair can work in your favour there too.
I’d go for a mid or high waist — it does all the quiet work of pulling an outfit together. And if you want a pair that carries you from Summer into Autumn, and even early Spring if you can get away with it, a mid-wash or light blue are the ones I reach for most. It’s slightly more relaxed looking than darker denim and I find it goes with pretty much everything.
Linen shorts
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I have both relaxed and slightly tailored linen shorts, and it’s the tailored pair I reach for most. Linen has such a beautiful natural structure that it feels a shame to lose it to something too slouchy — there’s more than enough time for that with our linen trousers. A little bit of shape here goes a long way.
When I say tailored, I don’t mean prim or overly quiet-luxury. It’s the small touches that count: a neat press crease down the front, a considered pocket detail. And one thing I always check — make sure if it has belt loops, that they run all the way around the waist. There’s nothing more annoying than a belt that keeps riding up at the back.
Relaxed casual shorts
For proper casual Summer shorts, French terry and a heavier cotton jersey are my best friends. They hang so much better than a thinner fabric and naturally give off that low-key, off-duty feel I’m always after. These are the shorts you throw on without a second thought.
My trick for keeping them from tipping into ‘too slouchy’ is to buy them as a set. Your outfit stays super relaxed, but a tonal co-ord quietly lifts it back into something elevated. French terry earns its place on holiday too — it soaks up the water after a swim and won’t leave those tell-tale damp marks, so it’s my go-to by the pool or the beach.
Tailored shorts
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We touched on tailoring with the linen, but you can absolutely take it further — a crisp 100% cotton, a bamboo blend, or, if you want a little drape, tencel looks beautiful with a pleat or two. This is the pair I’d steer any woman over 40 towards first: it makes an outfit look thought-through even when you’ve barely tried.
When wanting to create a high-low outfit pair something tailored with something unexpectedly low-key on top. A simple vest in the day, a plain camisole come evening. Let the shorts and their tailoring be the standout element, and contrast it with something simple on your bottom.
Bermuda shorts
Bermuda shorts are definitely having a moment so far this season, and you’ll spot them right across the high street in every colour combination going. The versions I love are tailored, straight-cut, and sit just above or well below the knee. In-between can read as mumsy.
This is where I lean into a bit of unexpected shoe theory. Style them with kitten heels, mules, or something a little more feminine on your feet, and the whole look shifts. That contrast between the longer, tailored short and a delicate shoe is what makes it feel considered and elegant — and I think it really works with this style of short.
Distressed denim shorts
Distressed shorts will always be a feature in my Summer wardrobe, every single year without fail — but this particular pair is the one I’m loving for 2026. I went true to size and they come up a touch big, brilliantly so. They don’t tug anywhere, there’s no pulling across the front, they look on trend, and the length sits exactly in my happy place.
What I like most is the restraint. The frayed hems add just enough detail without going overboard — no rips here, there and everywhere. It’s a nod to distressed denim rather than a full commitment to it, and that’s precisely what makes it work best for my style.
