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Much like our bodies, our wardrobes need to acclimatise to winter. It’s time to unpack your chunky knitwear and arm yourself with a waterproof coat or an umbrella at all times. And you can shelve your shoes and switch to boots instead.
It’s good to have a few pairs at your disposal so you’re covered no matter what you’ve got planned. Sophisticated brogues for a formal event. Hiking boots for outdoorsy activities. Boots with a fluffy lining for sub-zero temperatures. Or, if you’re following Timothée Chalamet’s lead, you could get a pair of black Timberlands and wear them for anything you’ve got in the diary.
But each style comes in many iterations, and it can be hard to know which pair to pick. Boots tend to have a higher ticket price than shoes, so you’ll want the ones you buy to last. It’s best to go for durable fabrics, such as leather or rubber, in timeless silhouettes, so you can wear them for years to come.
We’ve trawled independent brands, heritage labels and high-street stores to bring you the best boot styles to shop now.
The best men’s boots in 2026
Best lace-up boots:
Timberland Premium 6-Inch
Timberland
Premium 6-Inch
from £190
Thanks to Timothée Chalamet, Timberland’s 6-inch boots are back in the spotlight. Sure, they’ve been a staple ever since they became uniform for rap and hip-hop legends back in the 90s (Jay-Z, Nas, Biggie), but they’ve been a little quiet in recent years – until now.
His were customised by LA designer Chrome Hearts, but you can get the OG design directly from Timberland for less than £200. They’re waterproof. They’re warm. They’re versatile. And they’re comfy thanks to the anti-fatigue footbed that absorbs shock and returns energy to your feet. A solid choice, whether you’ve just won a Golden Globe or not.
Timberland
Premium 6-Inch
from £190
Best comfortable boots:
Birkenstock Highwood
Birkenstock
Highwood
from £95
Birkenstock may be best known for its sandals and clogs, but the German footwear expert also offers a great range of winter-ready boots. As with the high-profile sandals, the Arizonas and Bostons, the lesser-known Highwoods feature the label’s signature anatomically shaped footbed, meaning you can wear them all day with no complaint.
Birkenstock
Highwood
from £95
Best chelsea boots:
Arket leather
Designing pieces that last is Arket’s MO. The collections eschew trends for classics that you’ll wear for years, and everything is made with great fabrics and craftsmanship, so nothing will fall apart after a few outings.
These chelsea boots will probably be a part of your winter shoe rack for a long time to come. The sleek, laceless silhouette means you can easily dress them up with a suit, but they look equally good with a pair of jeans – and all you need to do is pull them on and go. Worth the investment.
Arket
Leather
£199
Best brogue boots:
Jones Bootmaker Fletcher
Jones Bootmaker
Fletcher
from £130
Brogues come in all shapes and sizes – derbys, oxfords, trainers or boots; they’re simply characterised by their elegant perforated uppers. Our first port of call on the high street for a classic take is Jones Bootmaker. The Fletcher has been given a modern twist with an easy-access zipper.
Jones Bootmaker
Fletcher
from £130
Best weatherproof boots:
On Cloudrock mid waterproof
On
Cloudrock mid waterproof
from £167.89
On is a technical footwear expert. Though it’s best known for its running collection, which originally became popular thanks to the brand’s CloudTec technology (hollow pods in the sole for soft landings and explosive take-offs), it has a good selection of boots built for the outdoors, too.
These are waterproof and have a chunky tread for extra grip when it’s slippy. They’re actually intended for hiking, but they’d work just as well when it’s rainy in the city.
On
Cloudrock mid waterproof
from £167.89
Best chukka boots:
Grenson Clement
If you’re not yet familiar with heritage shoemaker Grenson, you’re in for a treat. Although the Northamptonshire-based label has more than 155 years’ experience in the business, the designs today feel fresher than ever – and I wear them more than any other shoes I own. From a chunky, triple-cleated loafer to the trademark lightweight rubber soles (used in these chukkas), the brand is constantly innovating while staying true to its history.
Grenson
Clement
£335
Best chunky boots:
Dr Martens 1460 Ambassador
Dr Martens
1460 Ambassador
£170
Dr Martens is a brand that needs no introduction. Originally a punk staple worn by the likes of the Clash and the Sex Pistols, the boots have since become a popular grungy choice worldwide. These are a soft-leather version of the original 1460, so all the DM trademarks are included: yellow stitching, heel loop and PVC sole; they’re just a little comfier than the OG.
Dr Martens
1460 Ambassador
£170
Best suede boots:
Myrqvist Granhult
Myrqvist has a great selection of suede boots to choose from – and our favourite is the Granhult. Each boot is made using just one piece of first-rate water-repellent suede, which is Goodyear welted to a rubber sole. The brand sells direct-to-consumer to limit the margins and make high-end shoes more accessible.
Myrqvist
Granhult
£287
Best hiking boots:
Salomon Exvantage Mid
Sports label Salomon is the home of cool-guy outdoorsy footwear – and you’ll see them just as much on the pavements of east London as you would in the hills of the Peak District. These lightweight, waterproof, high-traction boots are extremely practical, but they’re also a low-key fashion flex thanks to the label’s signature triangular pattern on the side.
Salomon
Exvantage Mid
£98
For more hiking footwear, read our guide to the best men’s walking boots
Best value for money:
M&S leather chelsea boots
M&S
Leather chelsea boots
£89
If you’re looking for value for money, Marks & Spencer is usually your best bet. It has a solid selection of menswear basics, from jeans to tailoring, T-shirts to outerwear, all at a great price. When it comes to chelseas, I’d generally recommend opting for quality fabrics that are more likely to last – real leather rather than a PU fabric upper, for example. Luckily, M&S has a few that fit the bill for less than £100 – and these ones are waterproof too.
M&S
Leather chelsea boots
£89
Best lined boots:
Ugg Classic mini GTX boot
Ugg
Classic mini GTX boot
£230
Uggs for men are nothing new – the brand counts Justin Bieber, Pharrell Williams, Pete Davidson and Adam Sandler among its star fanbase – but the GTX is a fresh addition. Where the brand’s original ankle boots aren’t weatherproof, these feature a hardy Vibram sole and a waterproof Gore-Tex lining. And, of course, they have the signature furry lining.
Ugg
Classic mini GTX boot
£230
Best dress boots:
Charles Tyrwhitt leather chelsea boots
Charles Tyrwhitt
Leather chelsea boots
£199
If you have any formal events coming up, you’ll need the boots to match. A sleek pair of leather chelsea boots with a slim sole, soft suede lining and padded insole is the perfect solution. Tailoring expert Charles Tyrwhitt has just the pair.
Charles Tyrwhitt
Leather chelsea boots
£199
Best premium leather boots:
Russell & Bromley Scafell
Russell & Bromley
Scafell
£350
Russell & Bromley has been providing the UK with premium footwear on the high street for more than 150 years.
The Scafell is made in Portugal using a high-shine leather upper and finished with a leather sole that’s been upgraded with rubber detailing for extra grip. They’re the tallest in this edit, so they’ll give you extra coverage when it’s particularly cold out; just make sure you wear trousers that are wide and long enough to cover the brim, otherwise you’ll visually shorten your legs.
Russell & Bromley
Scafell
£350
Best wellington boots:
Hunter Downpour short wellington boot
Hunter
Downpour short wellington boot
from £72.95
For wellies, head to Hunter. These are made from natural rubber that’s been vulcanised, meaning it’s been under intense heat and pressure to ensure it’s fully waterproof – and the logo carries a little cachet, too.
My favourite is the more contemporary short silhouette. Not only does it look a little cooler, but, speaking from experience, it’ll also be much easier on your calves if you ever forget your boot socks – wearing wellies with ankle socks is a disaster waiting to happen.
Hunter
Downpour short wellington boot
from £72.95
Best minimal boots:
Vagabond Cameron boots
Vagabond
Cameron boots
£175
Scandinavia is often the best place for minimal classics that prioritise craftsmanship – and when it comes to footwear, look no further than Vagabond. The Swedish designer always stays true to its Scandi roots, and the Cameron are a case in point. They’re super simple. No laces. No elasticated side panel. Just a quality leather upper with a nice, cosy lining, paired with a chunky lug sole. All of the basics, elevated.
Vagabond
Cameron boots
£175
For more, read the best men’s suits under £400 and how to buy secondhand clothes online that you’ll actually wear
Peter Bevan is a stylist and fashion journalist covering menswear, womenswear and beauty
