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10 Best Winter Boots for Men UK 2023 | Dr Martens, Timberland and More

If you value your comfort, then as the colder, wetter months arrive, you’ll want to stow away your trainers and pull out a pair of reliable boots. The winter boot is the original footwear of the trenches, the shipyard worker and the hiking trails, so you can rest assured that a good pair will see you through those treacherous 15 minutes at the bus stop on a chilly January morning.


In this article, we're here to help you select a practical and durable pair of mens boots to keep your feet dry and warm. We run down everything you need to know from weather proofing to rubber soles, before sharing our ranking list of the top 10 best in the UK. Whether you're after a leather work boot or a vegan pair to help you dodge the ice, read on to discover our favourites from Amazon, ASOS and John Lewis!

Last updated 14/07/2023
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Table of Contents

How to Choose Winter Boots for Men in the UK – Buying Guide

It’s fair to say there are a wide array of choices when it comes to finding the right winter boot! Although the aesthetic will play a big part, there are some other factors to consider too. In this section, we’ll be taking a closer look at these nuances. 

1

Choose a Style That Will Suit Your Needs

The first factor you’ll need to consider is the style of boot you want. Now, if we were to go through all the different styles of bloke’s boots, we would need a much bigger word count. So instead, we’ve grouped them into three easy categories – formal, casual and technical. 

Look for Formal Boots if You Want to Maintain a Sharp Look

Look for Formal Boots if You Want to Maintain a Sharp Look
Source:amazon.co.uk

If you're keen to maintain a sharp look throughout the colder months, but the extreme drop in temperature has taken the oxford shoes off the table, don’t fear! There are still many formal styles that you can turn to. 


The formal or dress boot, such as a classic Chelsea boot or brogue boot, adopts timeless characteristics and silhouettes from more traditional shoes. The difference is, they’ll reach higher up the ankle and have better-equipped soles. If you’re looking to keep it professional, stick to classic colours like browns and blacks.

Casual Boots Look Elegant and Are Still Easy to Wear

Casual Boots Look Elegant and Are Still Easy to Wear

A casual boot will be stylish, yet easy to wear, and look smart with practically anything. This style will usually have a lower height than either formal or technical boots with fewer eyelets for the laces.

 
Some of the most popular styles are the desert boot, chukka boots and the classic Timberlands. While this style works well in winter with thicker socks and other weather-appropriate attire, they’re really the only boot that can make the transition to summer months due to their lighter construction. 

Technical Boots Are Perfect for the Man Who Prioritises Function Over Aesthetic

Technical Boots Are Perfect for the Man Who Prioritises Function Over Aesthetic

Technical and hiking gear seem to be having a bit of a moment in fashion right now, and if we’re being honest, we love it! These types of garments are great for outdoors-y types as they have specific features that protect in trickier terrains and challenging climates


Technical boots will provide excellent weatherproofing, and total coverage, which in turn means more security and stability. However, due to their cumbersome nature, they could have limited flexibility and movement. 

2

The Material You Choose Can Affect the Price and Durability

The Material You Choose Can Affect the Price and Durability

Another important choice is what material they are made from. The most common, and obvious choice is leather. This is because leather is hard-wearing and durable, comfortably outlasting other materials in this arena. They’re also waterproof and offer natural support to your feet, though it’s worth remembering that leather often requires breaking-in. 


However, not everyone will want to wear products made from animal skins. In which case, you have two options; boots made from synthetic materials such as polyester, nylon or canvas will be lighter and can be worn straight from the box. They’re often cheaper too! They just won’t be as durable, or as weatherproof, unless they come with a lining (more on this later). 


You may instead want to try a pair of boots made from faux leather or faux suede. These materials are created using a plastic base which is then treated with wax, dye or PU (polyurethane) to get the same colour and texture as the material they’re imitating. The biggest selling point is that you can get a similar look and feel to the original, without the harm caused. 

3

Waterproofing Will Help You Avoid the Dreaded Soggy Socks

Waterproofing Will Help You Avoid the Dreaded Soggy Socks

The world seems more divided than ever at the moment, but here at MyBest, we are certain there is one thing that we can all agree on – no one likes having soggy socks!


Any winter boots worth their salt would be considered waterproof. However, some materials, such as suede, will require additional treatment. This is usually in the form of a spray that you will need to top up so the boots can maintain their water resistance. So, to avoid any unpleasant surprises, it's always a good idea to check before buying.

4

Look for a Lining for Added Comfort and Warmth

Look for a Lining for Added Comfort and Warmth

This is a surprisingly infrequent feature, so you're most likely only going to find a lining in casual styles that focus on comfort and some technical boots. A good lining will take away the need for thick winter socks and will usually be made from insulating synthetic materials or wool. You might prefer a waterproof lining, such as Gore-Tex, especially if the outer material isn’t already waterproof.


As a boot provides more coverage than your trainers or other shoes, they tend to offer more warmth anyway. So, while a big thick woolly lining may sound tempting initially, it’s important to think about where you’ll be wearing them. If you’re going to be spending more time on the tube than walking, then you could end up with very sweaty feet. 

5

Have They Got Sole?

Have They Got Sole?

Along with the colder weather, often comes rain. Wetter weather means slippery pavements, which is something that can be particularly hazardous. One way of giving yourself a better chance against these perilous situations is by picking up winter boots with a trusty sole


The best bet is a pair of boots with a rubber sole, which most companies prefer to use. This is because the material is durable, slip-resistant, waterproof and generally hard-wearing.


The other options available are PVC, which insulate heat well but aren’t the best when it comes to grip, or synthetics which are lighter, more flexible and good at absorbing impact. However, neither of these materials are anywhere near as reliable as rubber. 

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Top 10 Best Winter Boots for Men in the UK

So, without further ado, let’s take a look at our top 10 favourite winter boots for men. We have footwear for every occasion, so we’re sure there’ll be something for everyone in our ranking! 
Popularity
Products
Image
Click to purchase
Key features
1

Clarks Originals

Desert Boot

Clarks Originals Desert Boot 1枚目

Possibly the Most Beloved Men's Boot Ever Made

2

ASOS Design

Chelsea Boots

ASOS Design Chelsea Boots  1枚目

Tremendous Value for Money

3

Timberland

Classic 6-Inch Premium Waterproof Boots

Timberland Classic 6-Inch Premium Waterproof Boots 1枚目

An Iconic Boot Known for Its Quality

4

Red Wing

875 Moc Toe Boot

Red Wing 875 Moc Toe Boot 1枚目

From the 1950s With Love

5

UGG

Campout Chukka Classic

UGG Campout Chukka Classic 1枚目

Take Your Slippers for a Walk

6

Dr Martens

Vegan Chelsea Boot

Dr Martens Vegan Chelsea Boot 1枚目

Winter Boots That Are Truly for Everyone

7

Aldo

Chagan Leather Lace-up Boots

Aldo Chagan Leather Lace-up Boots 1枚目

Modern Boots With an Old School Feel

8

Grenson

Fred Brogue Boot

Grenson Fred Brogue Boot 1枚目

A Classy Pair of Winter Boots That Toe the Line Between Formal and Casual

9

Inov8

Roclite 345 Gore-TEX Trail Walking Boots

Inov8 Roclite 345 Gore-TEX Trail Walking Boots 1枚目

The Ultimate Technical Choice

10

ASOS Design

Cuban Heel Western Chelsea Boots

ASOS Design Cuban Heel Western Chelsea Boots 1枚目

For Men Looking to Make a Statement

If you don't see the product you're looking for, you can request that it be listed.
No.1

Clarks OriginalsDesert Boot

Desert Boot Image 1
Source:asos.com
Desert Boot Image 2
Source:asos.com
Desert Boot Image 3
Source:asos.com
Reference price
£80.00
Reference price
£80.00

Possibly the Most Beloved Men's Boot Ever Made

The monumentally successful Clarks Originals Desert Boot is quite possibly the most beloved men's boot of all time! Originally conceived by Nathan Clark, the grandson of the owner, the boots initially floundered in the UK only to gain notoriety in the Americas in the 1940s. As they say, the rest is history. 


The boots have a wonderfully simplistic and unpretentious design that allows them to effortlessly slip between casual and formal. Of course, once the weather warms up don't be afraid of trying them with shorts, you won't be the first we've seen in this combination! 

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No.2

ASOS DesignChelsea Boots

Chelsea Boots  Image 1
Source:asos.com
Chelsea Boots  Image 2
Source:asos.com
Reference price
£55.00
Reference price
£55.00

Tremendous Value for Money

The Chelsea boot is an absolute staple of any winter wardrobe. The simple and elegant shape means this boot can be paired with practically any outfit, without ever looking out of place. The only problem comes when finding the best pair.


Now, if you're after the best value for money, you can't go wrong with this pair. Coming in at just over £50, these ASOS own brand boots are made from 100% real leather for a long-lasting pair that will make sure your feet stay dry throughout the colder seasons. 

No.3

TimberlandClassic 6-Inch Premium Waterproof Boots

Reference price
£180.00

An Iconic Boot Known for Its Quality

There are few boots with a more iconic silhouette than the classic 6-inch Timberland. The nubuck leather outer maintains all the qualities of traditional leather boots, but with increased breathability and flexibility. This added versatility means they're just as capable in the great outdoors, as they are for providing an urban look.


One of the distinctive features is the padded collar, which gives the boot an added touch of comfort. It's also worth mentioning that these boots have rust-proof toe caps, proving that quality is more than just skin deep. 

No.4

Red Wing875 Moc Toe Boot

Reference price
£269.00

From the 1950s With Love

We think it's a testament to the quality of Red Wing products that these boots were originally introduced to us in the 1950s, yet here we are in 2020 still talking about how they're some of the best winter boots around!


The Moc Toe boot was crafted with farmworkers and hunters in mind, so you can rest assured, they're built to withstand harsh weather conditions. This makes them perfect for any modern gentleman who is looking for a pair of hard-wearing and durable winter boots. 

No.5

UGGCampout Chukka Classic

Reference price
£116.70

Take Your Slippers for a Walk

Who hasn't dreamed of having the same comfort from their trainers as they would from a pair of fuzzy slippers, never mind winter boots! Luckily, the big wigs at UGG have come up with these wonderful winter boots you can wear outdoors, with the comfort of indoor shoes.


The suede boots feature decorative stitching on the outside that give them a classic chukka boot look. But the main event is the wool lining which adorns the inside, guaranteed to keep you toasty all through winter!

No.6

Dr MartensVegan Chelsea Boot

Reference price
£144.98

Winter Boots That Are Truly for Everyone

Thanks to the ever-growing prevalence of veganism around the world, our nature-loving brothers no longer have to spend winters with wet socks inside a pair of canvas pumps. These faux leather, unisex boots from Dr Martens expertly utilise modern textiles that allow the wearer to stay dry, look good and not hurt a soul while doing it. 


We love the versatility of classic Docs as they can be worn by anyone, from the postman to punks. The shoes are made from 70% faux leather, the other 30% being elastane, that ensures these boots are easy to slip on and off

No.7

AldoChagan Leather Lace-up Boots

Chagan Leather Lace-up Boots Image 1
Source:asos.com
Chagan Leather Lace-up Boots Image 2
Source:asos.com
Reference price
£78.00
Reference price
£78.00

Modern Boots With an Old School Feel

Looking like something Leo would have worn in The Revenant, or Edmund Hillary used to ascend Everest, these boots are for blokes who like to keep things casual, but with a touch of old-school technical aesthetics. 


The outer of the boots are made from 100% leather so you can rest assured you're feet will remain dry, with a faux shearling lining that will keep your trotters toasty. They even have a rubber sole with thick tread to prevent you from slipping off the pavement when it starts to get icy outside.

No.8

GrensonFred Brogue Boot

Reference price
£295.00

A Classy Pair of Winter Boots That Toe the Line Between Formal and Casual

Founded in 1866, Grenson opened their first factory in Northampton in 1874 and have been making their very well-respected shoes there ever since. Known for their handmade brogues and Chelsea boots, these winter boots are based on the brand's famous Archie brogue shoes


This pair includes the incredibly popular triple welt (three-layered) sole and oversized punching with large eyelets. They're pricey, but if you're looking for a pair of classy boots, these will do the job very well. 

No.9

Inov8Roclite 345 Gore-TEX Trail Walking Boots

Roclite 345 Gore-TEX Trail Walking Boots Image 1
Source:amazon.co.uk
Roclite 345 Gore-TEX Trail Walking Boots Image 2
Source:amazon.co.uk
Roclite 345 Gore-TEX Trail Walking Boots Image 3
Source:amazon.co.uk
Reference price
£139.49
Reference price
£139.49

The Ultimate Technical Choice

If you're all about practicality, then these babies from Inov8 have that in abundance! These technical hiking boots are built using synthetic materials to keep their weight down, which could become a problem when the heavens open, but thanks to their Gore-Tex lining, your hooves will stay bone dry.


On top of that, they've got a rubber sole infused with Graphene for additional strength and flexibility. These efficient boots even came number one in our hiking boots for men article, we just don't think most folks need this much functionality for walking around their town center. 

No.10

ASOS DesignCuban Heel Western Chelsea Boots

Cuban Heel Western Chelsea Boots Image 1
Source:asos.com
Cuban Heel Western Chelsea Boots Image 2
Source:asos.com
Reference price
£24.50
Reference price
£24.50

For Men Looking to Make a Statement

Getting us underway are these unique boots from ASOS's own line. They're surely a niche choice, but if you're the type of man who likes to make a statement, while still keeping things smart and formal, then these are surely going to do just that! 


They're competitively priced, coming in well under £30. However, they'll need a protective spray if you require them to be waterproof. Further, we were unable to find what the sole is made from, so can't guarantee how sturdy they'll be. But if nothing else, they'll certainly add a bit of pizzazz to your wardrobe.   

Keep Warm This Winter

Keep Warm This Winter

Blink and before you know it, winter is well and truly upon us. This year, don't get caught out in the cold. Take a look at the links below for some of the best men's clothing and accessories to see you looking good and feeling toasty all throughout the season!

Summary

So there it is, our comprehensive guide to picking the perfect pair of winter boots. Whether you're searching for a smart pair for the office, or something you can slip on before you head out for a winter wander, we hope you've found this article useful. Who knows? You might even need a second pair with how long our winters seem to last! 


Author: Lewis Clark

Top 5 Winter Boots for Men

No. 1: Clarks OriginalsDesert Boot

No. 2: ASOS DesignChelsea Boots

No. 3: TimberlandClassic 6-Inch Premium Waterproof Boots

No. 4: Red Wing875 Moc Toe Boot

No. 5: UGGCampout Chukka Classic

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The descriptions of each product are referenced from content available on manufacturer, brand, and e-commerce sites.
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