As the colder months set in, a reliable pair of boots becomes an essential part of any man's wardrobe. Our fashion expert has curated a selection of the top 15 boots to suit every occasion, ensuring you stay stylish and prepared for whatever winter brings.
Why Boots Are a Winter Wardrobe Staple
Much like our bodies need to adjust to the chill, our clothing choices must evolve with the seasons. It's time to embrace chunky knitwear, waterproof coats, and, most importantly, sturdy boots. Having a few pairs on hand allows you to tackle any event, from formal gatherings to outdoor adventures.
Sophisticated brogues can elevate a suit for a black-tie affair, while hiking boots provide traction and support for countryside walks. For sub-zero temperatures, opt for boots with a plush lining, or follow the trend set by Timothée Chalamet with versatile black Timberlands that work for nearly any activity.
Choosing the Right Boots for Longevity
With so many styles available, selecting the perfect pair can be daunting. Boots often come with a higher price tag than shoes, so investing in durable materials like leather or rubber is key. Timeless silhouettes ensure your boots remain fashionable for years, making them a worthwhile addition to your collection.
We've scoured independent brands, heritage labels, and high-street stores to bring you the finest boot styles available now.
Top Men's Boot Picks for 2026
Best Lace-Up Boots: Timberland Premium 6-Inch
Thanks to Timothée Chalamet, Timberland's iconic 6-inch boots have regained popularity. Originally a staple in 90s hip-hop culture, these boots are waterproof, warm, and versatile. The anti-fatigue footbed offers comfort by absorbing shock, making them ideal for any occasion, whether you're attending a glamorous event or a casual outing.
Best Comfortable Boots: Birkenstock Highwood
While Birkenstock is renowned for sandals, their Highwood boots feature the same anatomically shaped footbed, ensuring all-day comfort. Perfect for winter, these boots combine practicality with the brand's signature support.
Best Chelsea Boots: Arket Leather
Arket focuses on timeless designs crafted from high-quality materials. Their leather Chelsea boots boast a sleek, laceless silhouette that pairs effortlessly with suits or jeans, offering a smart investment for your wardrobe.
Best Brogue Boots: Jones Bootmaker Fletcher
Brogues are defined by their elegant perforated uppers, and Jones Bootmaker's Fletcher model adds a modern twist with an easy-access zipper. This high-street option delivers classic style with contemporary convenience.
Best Weatherproof Boots: On Cloudrock Mid Waterproof
On, known for its running shoes, offers these waterproof boots with a chunky tread for enhanced grip. Designed for hiking, they're equally effective for navigating rainy city streets.
Best Chukka Boots: Grenson Clement
Heritage shoemaker Grenson brings over 155 years of expertise to these chukka boots. Featuring innovative lightweight rubber soles, they blend tradition with modern freshness.
Best Chunky Boots: Dr Martens 1460 Ambassador
Dr Martens' soft-leather version of the classic 1460 boot retains iconic details like yellow stitching and a PVC sole, but with added comfort. A grungy staple that has stood the test of time.
Best Suede Boots: Myrqvist Granhult
Myrqvist's Granhult boots are crafted from a single piece of water-repellent suede, Goodyear welted to a rubber sole. Sold direct-to-consumer, they offer high-end quality at accessible prices.
Best Hiking Boots: Salomon Exvantage Mid
Salomon's lightweight, waterproof boots provide high traction for outdoor activities. Their stylish design, featuring a signature triangular pattern, makes them a fashion statement in urban settings too.
Best Value for Money: M&S Leather Chelsea Boots
Marks & Spencer delivers excellent value with these waterproof leather Chelsea boots under £100. Made from real leather, they promise durability without breaking the bank.
Best Lined Boots: Ugg Classic Mini GTX Boot
Ugg's GTX boot combines a waterproof Gore-Tex lining with the brand's signature furry interior. A hardy Vibram sole ensures these are suitable for harsh weather, loved by celebrities and everyday wearers alike.
Best Dress Boots: Charles Tyrwhitt Leather Chelsea Boots
For formal events, Charles Tyrwhitt's sleek leather Chelsea boots with a suede lining and padded insole offer sophistication and comfort, perfect for pairing with tailored suits.
Best Premium Leather Boots: Russell & Bromley Scafell
Russell & Bromley's Scafell boots, made in Portugal from high-shine leather, feature a leather sole with rubber detailing for grip. Their tall design provides extra coverage in cold conditions.
Best Wellington Boots: Hunter Downpour Short Wellington Boot
Hunter's vulcanised natural rubber wellies are fully waterproof. The short silhouette offers a contemporary look and is easier on the calves, making them a practical choice for wet days.
Best Minimal Boots: Vagabond Cameron Boots
Vagabond's Cameron boots embody Scandinavian minimalism with a quality leather upper and chunky lug sole. Simple yet elevated, they prioritise craftsmanship for a timeless appeal.
This guide ensures you're equipped with the best boots to face winter in style. Whether you're braving the elements or dressing up for an event, these picks cater to every need and budget.
