The UK’s often brisk autumn and winter weather doesn’t make it easy to bare legs. But with boots and substantial socks and/or tights, it is possible to wear a skirt or dress during the cooler months and not immediately regret your decision.

Read more: The Key Autumn/Winter 2026 Trends To Know Now

Midi lengths are especially versatile: unlike a mini, midis cover a little more leg (bringing a little more warmth). Plus, your chosen boat remains on full show with a midi, which would otherwise be covered by a maxi. Boot-wise, knee-highs of any variety – cowboy, suede, pointed with heels, flat riding boots – are perhaps the best style, given they envelop your calves with sturdy leather or suede, providing extra insulation, and they don’t hit your legs at an awkward point.

Ankle boots are harder to style with midi-skirts, and they can err into unflattering territory. To ensure they don’t look outdated, consider loose-fitting slouchy styles or chunky bikers that sit a bit higher and leave room between your shin and the boot. Sock boots are a feasible option, but only if they’re styled right – they’re inherently offbeat and futuristic, and therefore need to look intentional. Scroll on for midi-skirt and boots outfit ideas to embrace this autumn.

Elinor Oversized Wool Bomber Jacket