The cold weather has well and truly descended, bringing with it the opportunity to showcase your winter style for another season. We’re talking chunky knits, hard wearing denim, cosy coats, and of course, your favourite boots - those winter footwear companions that will see you through the rainy days when a pair of trainers just won’t cut it.
We’re not talking the sleek, lightweight styles that were your summer go-tos - forget suede chukkas, supple leather Chelseas or leather-soled deserts.
Instead, you should be on the lookout for chunky rubber soles, full-grain leather, and water-resistant wet weather warriors. Work boots, substantial Chelseas, and warm hiking boots should all feature on your new season wishlist.
When wearing a heftier style, pair them with rolled up denim, straight leg work pants, or substantial wide leg tailored trousers. If your preferred fit on the bottom half is on the narrower side, look to the Chelsea and chukka silhouettes that will work with slim or tapered trousers - just make sure you steer clear of styles that will leave your feet feeling soggy after an accidental foray into an unseen puddle.
As a staple that never goes out of fashion, it’s worth investing in a quality pair that will see you through this season and beyond. Look out for Goodyear-welted and Vibram soles for boots that you can rely on to stand the test of time - as long as you stick to the black, brown, and tans of the world, you’ll be sure to wear them for years to come.
So, it’s time to protect yourself from the rain in a pair that we’ve carefully selected below.
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Grenson Asa
Though British heritage brand Grenson has a history that dates back to 1866, the brand designs some of the most contemporary boots on the market, featuring lightweight chunky soles, fresh silhouettes, and modern design features, all the while staying true to a timeless aesthetic.
From the tonal neutral colourway to the airy white wedge sole, the Asa boots are a case in point.
Buy now £340.00, Grenson
Axel Arigato Blyde Chelsea
Handmade in Portugal using full-grain leather, Axel Arigato’s chelsea boots are chunky, contemporary, design of the utmost quality.
Featuring a pull tab and elasticated inserts so you can easily slip them on and off, a discreet jacquard tab label, as well as an embossed logo on the rubber sole, these will finish off any cold-weather-look in style.
A great alternative if you’re partial to the Prada look but without the price tag.
Buy now £360.00, Axel Arigato
Vagabond Jeff Boots
Swedish brand Vagabond, which began life in the Seventies as a men’s footwear brand, has since expanded to include a wide range of men’s and women’s shoes.
Crafted in a black leather, the Jeff is an elevated utility boot that would work best worn with, well, just about anything.
Buy now £175.00, Vagabond
Russell & Bromley Saxman Moccasin Cleated Sole Chukka Boot
Every man needs a quality pair of chukkas in his footwear arsenal - and Russell & Bromley's design fits the bill nicely. True to the brand's MO, they're expertly constructed using premium fabrics for a pair of shoes that will last.
Buy now £245.00, Russell & Bromley
Dr. Martens 2976 DM's Wintergrip Leather Chelsea Boots
From the loop tag to the trademark sole, you can spot a pair of Docs a mile off.
Arguably the most identifiable pair of boots in the edit, the 2976 is the brand’s original Chelsea boot design that dates back to the 70s. This particular pair are fleece-lined and boast slip-resistant grip - it doesn't get more winter-proof than that.
Buy now £180.00, Dr. Martens
Clarks Rossdale Mid Beeswax Leather
With an archive dating back nearly 200 years, Clarks is a label that knows its way around a pair of boots.
Combining weatherproof features with quality craftsmanship, these are a durable style designed for all-day comfort.
Buy now £120.00, Clarks
Cheaney Stirling C Chukka Boot in Jet Black Kudu Leather
If you’re into a chukka boot, Cheaney’s fully leather lined design with a Goodyear welted double commando rubber sole is the upgrade you need for winter.
Made in the same Northamptonshire factory since 1896, the brand is a staple in the UK’s famous shoemaking industry - and has an expertise that shows. If you wear them into the ground, the brand also offer a refurbishment service using the same techniques as when they were first made.
Buy now £225.00, Cheaney
Church’s Mc Farlane Lw Highland Grain Lace-Up Boot Brogue Black
If you’re partial to the ornate design of a brogue, who’s to say that needs to stop with your shoes?
Italian brand Church’s, owned by the Prada group, design the best of the best. Crafted using full grain leather with a natural finish for a textured look, a Goodyear construction for added durability and a lightweight Commando rubber sole, these are boots that will live in your collection for years.
Buy now £1070.00, Church’s
Ariat Sport Stratten Western Boot
Spotted on the runway at Celine, Prada and Dries Van Noten, cowboy boots have become a must-have - no matter what the season. Go back to the style’s roots with equestrian brand Ariat, who are, in fact, the official sponsors of Professional Bull Riders. Yee-haw.
Buy now £165.00, Ariat
Diemme Roccia Vet leather hiking boots
If you’re likely to find yourself on a hiking adventure in the near future and want to invest a pair of boots that will do double duty on the streets of London, look no further than Italian label Diemme.
With a lug sole for extra stability on tricky terrains and hiking-inspired laces, they’re ideal for conquering mountains and city parks alike. And, trust us, we won’t judge you if your rambling doesn’t go beyond the concrete jungle.
Buy now £359.00, Matches
Prada Monolith Brushed Leather Chelsea Boots
The holy grail of chunky footwear, Prada’s iconic rubber sole that features on loafers, derbies, sandals, and boots, is a celebrity and fashion crowd favourite.
These leather Chelseas boast are surprisingly lightweight given the oversized sole - and the sleek polished finish makes for the perfect understated statement.
Buy now £1100.00, Prada
Charles Tyrwhitt Waxed Suede Boots
If you're in the market for both style and substance - and let's face it, who isn't? - look no further than Charles Tyrwhitt's waxed suede lace-ups. Naturally water-repellent, lightweight, durable and comfortable, they go the extra mile for both comfort and style.
Buy now £199.95, Charles Tyrwhitt
