Best winter shoes for men

The ultimate cold-weather footwear guide

The checklist for men’s footwear that’ll see you through winter’s darkest days features characteristics such as sturdy, reliable, weatherproof and stylish. Don't be afraid to up your budget because the best quality winter shoes or boots will last for years, especially timeless styles such as brogues, Chelsea boots or chukka boots. These varied styles help you transition effortlessly between office days, weekend pub lunches and winter walks.

Damp city streets? No problem, thanks to the go-with-everything, smart-casual classic Chelsea boots. Invest in a great pair in leather or suede as an essential building block of your winter wardrobe, and they’ll elevate even the simplest everyday denim and casual separates.

Designed by an Italian mountaineer in the 1930s, these boots have a deep-tread rubber sole with chunky indentations (called lugs) and supportive ankle coverage. Ideal for country walking, but – paired with dark jeans and a thick knit – streamlined and refined enough for weekend pub visits.

If sleet is forecast but you need to head to the office, you’ll be hard-pressed to find something as trustworthy as the timeless brogue. Opt for a thicker sole for extra winter-proofing and care for the leather of this investment purchase. Loake, which has just landed at John Lewis, is hard to beat.

For smart events or nights out, loafers will always rise to the occasion. They might not have the best grip for ice patches, but they’re more than able to keep your feet dry and supported. Go for the full ’80s preppy look, with colourful socks, tailored trousers and an Oxford shirt.

On drenched days when you have to leave the house – but would really rather not – walking boots are the real deal. Fully waterproof, supportive and with great tread, of course you can go hiking in them, or you can just wear them with denim to the pub and look like an outdoor-activities man.

This specific type of ankle-high desert boot is lighter, unstructured and designed for relaxed off-duty comfort, rather than full-on outdoor adventuring. Still providing great grip and support, chukka boots are dressier and easily work for smart-casual (but only if they’re clean…).

A flash of colour on your feet can break up a winter palette of charcoal, navy, chocolate and black. Designed for urban exploration, sturdy suede sneakers combine function and fashion – see the walking-inspired new brand Flower Mountain. With a bit of care they’ll be winter-proof.

Classic white trainers are the backbone of any man’s wardrobes; worn with everything from tailored trousers to denim, a sturdy leather pair will see you through an urban winter. Look for the extra comfort and support of sportier designs, and always wear breathable socks.