Dressing for the cooler climes can often feel like a conundrum: layers upon layers, and still the nagging question of what works without looking too bulky. Footwear, however, is one of the easier puzzles to solve and the knee-high boot, in particular, deserves a special mention.

They sit just as comfortably alongside a tailored pair of trousers as they do with denim, and they carry skirts and dresses – short, sweeping or somewhere in between – into colder months. The best styles hit just below the knee, skimming rather than strangling the calf, unless you lean towards the glove-like fit of a trending skin-tight boot.

As is the case with investment-worthy pieces, longevity should always guide the choice. A towering heel may look dramatic when you try them on, but practicality is essential when you’re navigating pavements in October drizzle. Fit matters too, pointed toes can sharpen an outfit, but they can also punish the foot if the sizing is off – going up half a size is rarely a mistake, especially if you like to wear thick socks.

Scroll on for a guide to some of the best styles available now, and inspiration on how to style knee-high boots.

Autumn hues

With a maxi dress

The ’90s-inspired look

All black

Palladium-Plated Daria Chain Choker Necklace

With a miniskirt

Shop more knee-high boots…