12 Long Shorts You Can Wear Now & Into Winter

Go long with this pair of cream Wynn Hamlyn shorts. Photo / Wynn Hamlyn

Here are some lovely long shorts, because who doesn’t love a pragmatic, transeasonal wardrobe solution?

Some of you may feel somewhat nonplussed about what to wear right now.

One minute it’s muggy, the next you’re reaching for a cardigan on a particularly cool morning or evening. While there’s still some

Lately, I’ve been enjoying a return to a crisp pair of Dickie’s, a wardrobe item I haven’t worn since high school but somehow offers an easy solution for a smart-looking pair of shorts that aren’t too short or too tight, and can work particularly well with an academic twist — think a shirt with a vest, socks and loafers.

Shorts — particularly smart-looking shorts, as fashion assistant and stylist Annabel Dickson has complied below — are a great alternative to skirts or trousers and do something much better than the parade of Capri pants that TikTok is currently trying to make happen; they work with various body shapes and leave give you much more breathing space.

One quick-pro styling tip is to try a boxy pair of smart shorts with a pair of loafers or ballet flats. Come winter, shorts work particularly well with tights and knee-length boots.

These shorts will give you plenty of options to team with a shirt and blazer for the office. If it’s a nod to Patrica Field’s school of styling, then add a pair of mules and French tuck a going-out top into a pair of shorts for a subtle (and chic) alternative to after-five dressing. Fendi baguette bag optional.

A subtle houndstooth check print is a great option for chic work shorts.

A loose-fitted, mid-waisted short, these wool options also feature on the backside of the waistband, an exclusive Italian-made lamb leather coin purse.

The local brand offers up its fresh take on a low-slung, tomboyish short with double pleats.

For some texture, add a soft piece of knitwear on top for the perfect outfit formula when temperatures begin to cool.

Denim shorts have made an impact for all genders, and this easy pair has a hit of 80s nostalgia with its subtle wash.

For a crisp pair of shorts in classic black, this is a pair for every occasion.

The local brand makes a convincing case for a slinky short inspired by men’s boxers. Try these with a pair of heels for an irreverent going-out look.

Shorts with a 1950s bent, we’d style these slightly more fitted denim shorts with a soft blouse or shirt and a pair of ballet flats.

Another slightly fitted short option, these come with generous pockets for all your sundry items.

Corduroy is an ideal trans-seasonal fabric, and we love how this cream pair drapes and falls easily.

New to the market, Rebe offers some easy, minimalist wardrobe solutions with a twist.

The fashion doyenne’s brand knows how to cut a good pair of bottoms, and this easy short is perfect for work or weekend.

More shopping

What to buy now and love forever.

These pretty slip dresses are perfect for hot, slinky summer days. These simple styles will work for every occasion.

Go wide! Stride out in a pair of roomy, comfy trousers. Give your legs the space they deserve.

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