Designer men's boots for winter and beyond The Times Peter Bevan shopping Designer men's boots for winter and beyond new From classic Chelsea boots to suede chukkas Steve McQueen in The Great Escape, 1963 Silver Screen Collection/Hulton Archive/Getty Images Peter Bevan Monday October 12 2026, 4.00am BST , The Times Listen 0:00 / · 6:13 min Share Share this article Email Twitter Facebook Link Save Puzzles Challenge yourself with today's puzzles. Few things repay the investment quite like a good pair of boots. Choose well and you'll still be wearing them in 30 years. Like a leather jacket or a waxed Barbour, the best styles only improve with age. They don't date, either. The Chelsea boot was devised in the Victorian era as an elasticated riding boot (for Queen Victoria, or so the story goes) and has since been worn by everyone from the Beatles to Bowie and Sean Connery's Bond. The surest sign of a good pair is the sole: a Goodyear-welted or stitchdown construction means it can be resoled rather than having to replace it altogether once the sole has worn out. All recommendations within this article are informed by expert editorial opinion. If you click on a link in this story we will earn affiliate revenue Jump to Chelsea boots Utility boots Suede boots Lace-up boots How to style men's boots Even the best boots can be ruined by the wrong trousers. The leg needs to have enough width to fall over the shaft of the boot, so choose a straight or relaxed cut rather than anything slim or skinny that'll bunch up around the ankle. As for length, aim for a hem that just grazes the top of your foot when standing. It lengthens the leg and, frankly, looks far more expensive. Once your trousers are sorted, take your other styling cues from the boot. Utility styles call for easy separates such as a heavy knit or plain T-shirt. Suede pairs well with tactile textures like brushed cotton, while a smart Chelsea can take anything from an Oxford shirt to a full suit. Chelsea boots A leather Chelsea works with almost everything, from suiting to denim to workwear. For weekends in the country, a lug sole is more practical and balances out a wider jean. For tailoring, keep it slim with a sleeker toe and a leather sole. My favourite style sits somewhere between the two: a midweight pair with a rounded toe and rubber sole that's smart enough for tailored trousers but tough enough to handle a wet pavement. Advertisement Manolo Blahnik Elvetico Manny full-grain leather Chelsea boots ￡1,125, Manolo Blahnik at Mr Porter Grenson Baker Stitchdown boots ￡195, Grenson Paul Smith dark brown leather Xenon boots ￡295, Paul Smith RM Williams Signature Craftsman boots ￡750, RM Williams Utility boots These boots are practically built for winter but there's no need to save them exclusively for bad weather. Their rough-and-ready feel works just as well on a crisp, sunny day in the city, worn with a chunky jumper and sturdy workwear trousers. Look for waxed or oiled leather, which is helpfully waterproof, and a deep-treaded sole. Advertisement Dr Martens 1460 Crazy Horse leather boots ￡170, Dr Martens Diemme Roccia Vet Gomma black leather boots ￡439, Diemme at Farfetch Vagabond Cameron boots ￡175, Vagabond Our Legacy Tanker leather ankle boots ￡880, Our Legacy at Mytheresa Suede boots Suede boots look great with corduroy, flannel, cashmere — all of the cosy textiles that come back in autumn. And despite their reputation, they can handle a drizzly commute far better than you'd think if they're given a coat of protector spray. Chukkas are my top pick, with the low-key, off-duty ease Steve McQueen perfected long before east London caught on. Clarks desert boots are the original, adopted by everyone from the mods to Kingston's reggae scene and the Britpop crowd. For the office, a suede Chelsea or lace-up is more refined, and Tod's and John Lobb make the kind that'll see you through many winters. Advertisement John Lobb chukka suede boots ￡1,560, Mr Porter Tod's suede Chelsea boots ￡730, Tod's at Mr Porter Clarks desert boots ￡99, Clarks Gucci lace-up ankle boots with web detail ￡840, Gucci Lace-up boots The polished lace-up sits somewhere between a rugged work boot and a dress shoe. Like the Chelsea, it'll take you from suits to jeans, just with a little more heft. At the sharper end, the Oxford boot keeps things sleek with closed lacing and a slim shape. Add broguing (those decorative perforations) and it softens into something that feels at home with flannel and corduroy. If you're buying only one pair, make it a Derby. Its open lacing and rounder shape give it an easier, more versatile finish. Brunello Cucinelli's are a case in point. Advertisement Canali leather lace-up boots ￡650, Canali at Mr Porter Church's Edworth 2.0 boots ￡990, Church's Brunello Cucinelli leather ankle boots ￡1,250, Brunello Cucinelli at Mytheresa Boss Formal brushoff leather lace-up boots ￡269, Boss Why trust Times Luxx Shopping? Times Luxx Shopping is brought to you by the award-winning team behind Times Luxx magazine. For nearly 20 years, our experts have curated an unrivalled selection of the best in fashion, jewellery, travel, tech, cars, design, food, drink and more. That same rigour, taste and insider industry knowledge underpins Times Luxx Shopping. Every product and experience we recommend is thoroughly researched and vetted by our team. If we love it, we think you will too . Life & Style LUXX Men's fashion Gucci Share Share this article Email Twitter Facebook Link Save