Chelsea boots are one of those enduring wardrobe staples that designers return to season after season. They might be toughened up with lug soles and metallic hardware, or given a more polished feel with sleek pointed toes and sculptural heels, but the classic pull-on silhouette remains a constant footwear choice peddling the fashion circuit.

Brands from Prada to Totême and Tod’s have delivered their own interpretation – Western-inspired, sharp and slim, or unapologetically stompy. Slipping on with ease, the Chelsea boot works with most outfits and is as fitting for pounding city pavements as it is for a countryside stroll.

When it comes to finding the right pair, classic leather styles with a low or flat heel, a smooth sole and an almond-shaped toe are a reliable starting point. That said, there’s no shortage of more directional options, from leather boots with Cuban heels to chunky, treaded soles. Weather-resistant designs are also worth considering, particularly as the seasons change. Brands like Moncler, Barbour and Dr Martens offer practical takes on the silhouette, with rubberised soles and cosy shearling linings that make them well suited to unpredictable weather.

Need a little styling inspiration? Scroll on for inspiration on how to style Chelsea boots this season, whatever your plans may be.

With a trench + kilt

With jeans + a T-shirt

With a nightie dress

With a denim skirt

With tailored trousers

With a satin slip