12 Long Shorts You Can Wear Now & Into Winter

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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.

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