Best winter boots for men to get you through the colder months
The cold weather has well and truly descended, bringing with it the opportunity to unpack your autumn/winter wardrobe for another season. We’re talking chunky knits, hard wearing denim, cosy coats, and of course, your favourite boots - your 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 or Dainite 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 your tootsies from the rain in a pair that we’ve carefully selected below.
Grenson Augustus
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.
The Augustus boots are a monkey boot that have had a heavy duty makeover, with a rubber sole, a beaded toe cap, and wrap around rubberised bumper. The good news? If you like them, you can get them in black, too.
Buy now £335.00, Grenson
Prada 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 Chelsea boots boast a tall boot leg, a square toe, and are surprisingly lightweight given the oversized sole. An understated statement that would look best poking out from under a straight or wide leg trouser which is slightly pooling at the ankle. - if you know, you know.
Buy now £1200.00, Prada
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 sand-coloured nubuck, suede’s more durable sibling, the Jeff is an elevated utility boot that would work best worn with neutrals and whites. Though technically work boots, we’re sure these will be happiest under a pub table or striding the pavements on a chilly London evening - with no work in sight.
Buy now £175.00, Vagabond
Russell & Bromley Trial Hiker Lace Boot
Calling all of those gorpcore lovers, you’ll be pleased to hear that hiking is a trend that’s here to stay.
Inspired by the great outdoors, Russell & Bromley’s khaki boots, which are crafted from soft suede and rough textured rubber, are perhaps more suited to a ramble through Hyde Park as opposed to scrambling up Snowdonia - and who would want to ruin such a chic pair of boots with the prospect of a real hike, anyway? At least you’ll look the part.
Buy now £245.00, Russell & Bromley
Dr. Martens 2976 Yellow Stitch Smooth Leather Chelsea Boots
With an AirWair heel loop tag, yellow welt stitching and the iconic air-cushioned 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. Famously hardwearing, the smooth leather can be polished for a high shine or scuffed up for a grittier look. Goodyear-welted, they’ll last you a lifetime.
Buy now £159.00, Dr. Martens
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 £375.00, Cheaney
Clarks Chard Mid GORE-TEX Black Oily Leather
With an archive dating back nearly 200 years, Clarks is a brand that knows its way around a pair of boots.
Combining weatherproof materials with quality craftsmanship, the Chard boots are a durable style designed for all-day comfort. Breathable, windproof, and waterproof, the Gore-Tex membrane guarantees dry and comfortable feet no matter what the elements throw your way - no soggy soles to see here.
Buy now £120.00, Clarks
Ariat Rambler Western Boot
Spotted on the Spring/Summer 23 runways at Celine, Prada and Dries Van Noten, cowboy boots are on the rise - and where better to get them from than equestrian brand Ariat? Who, by the way, are also the official sponsors of Professional Bull Riders - it doesn’t get more cowboy than that.
Start by testing the waters with a classic pair of black or brown with contrast stitching before channelling your full John Wayne. Let’s just hope your walk doesn’t change, too.
Buy now £150.00, Ariat
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 with a storm welt for added durability, and a lightweight Commando rubber sole, these are boots that will stand the test of time.
Buy now £980.00, Church’s
Diemme Civetta Boot
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 Diemme’s Civetta boots.
With a Vibram sole for extra stability on tricky terrains, a statement red waterguard for unparalleled wet weather protection, and hiking-inspired laces, they’re ideal for both mountain and city use. And, trust us, we won’t judge you if your hiking doesn’t go beyond the concrete jungle.
Buy now £365.00, End Clothing