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In fact, it’s likely that most men will need more than one pair of boots to wear this autumn/winter season.
The reason for that is functionality: everyone needs a pair of solid waterproof boots they they can rely on when the rain starts to fall or the snow comes down, but a different pair entirely is needed if attending a social occasion.
Broadly speaking, most men’s boots can be categorized as Chelsea boots or chunkier boots which can be called hiker or walking boots.
Which ones you choose mainly depends on your personal style preference, but both are a great option. If you can’t decide between the two then you can always get one of each.
The most important thing is that you choose a pair that fits well and protects your feet from the elements.
For more winter wardrobe staples, check out our guides to the best men’s puffer jackets and also the best women’s winter boots.
Make sure the whole family is ready for winter too with these stylish rain boots for mum, dad and the kids, along with the top raincoats to suit men, women and children.
These gorgeous Chelsea boots are made from responsibly sourced leather which comes from a tannery audited and rated by the Leather Working Group.
The group which promotes responsible environmental practices across the leather supply chain.
This style of boot was first made popular in the 1950s and 19660s when worn on the King’s Road, Chelsea, in London - hence where the boot gets its name from.
These days, they are a timeless wardrobe staple.
Available in sizes 6 to 12, including some half sizes.
Step out in style in these soft nubuck chukka boots. Sturdy design combines comfort and support with a classic look with this boots which would be perfect for weekend strolling.
Lace-up fastening ensures a comfy and secure fit.
Even better, they are made with responsibly sourced leather so they’re good for you and good for the planet.
Available in two colours, sand (pictured) and dark tan. Also available in sizes 6 to 12, including some half sizes.
Be ready for adventure rain or shine with these waterproof walking boots.
They have a round-toe design with suede toe bumper and padded collar on the ankle for comfort.
They have a lace-up fastening with top hooks to secure so you can quickly lace up and be on the move, knowing your feet are supported while you take in the sights - whether you’re wandering through the woods or hiking through the mountains.
Freshfeet™ technology fights bacteria to keep boots smelling fresh all day too.
Available in sizes 6 to 12.
These black boots are an easy, everyday option - and at less than £24 they are a bargain.
They’ll go with any outfit you are wearing and the no fuss design with zip-side fastening means you can put them on and take them off in no time at all too.
They are made with smooth faux-leather and have a matte finish, while a slim toe keeps them looking stylish but not bulky.
Available in size 5 to 13.
In a bold cognac colour, these sturdy boots are made for the man who wants to stand out from the crowd.
Selected Homme are a brand which puts a Scandi twist on contemporary styles - hence the mix of soft teddy lining, colour and chunky design.
They’re made of real leather too, hence the more expensive price tag, but they are an investment as these are boots you’re going to want to wear season after season.
Available in size 6.5 to 12.5.
Fashion icon Calvin Klein is known for putting a designer stamp on clean, casual-cool staples - and these brown boots are no exception.
They feature elasticated inserts and a pull tab for a comfortable fit and effortless style.
There’s also a chunky sole with textured tread on these boots - and while the soft suede material means they’re not suitable for all weathers you can be sure of a strong grip underfoot so no slipping on autumn leaves.
They might not be waterproof, but these boots are the best option for autumnal evenings out when you want to feel a bit smarter and dress up.
Complete with the Calvin Klein logo on the side of the boots.
Available in sizes 6.5 to 11.
An online exclusive product, these boots offer all the comfort and style of a suede boot - without hitting your wallet hard.
The soft grey colour is a nod to the season and ensures that these are a neutral pair of boots which will go well with everything in your wardrobe.
They feature elasticated sides and a pull tab so you can quickly slide them on and off without slowing down.
Available in size 6 to 12.
These chunky military style boots are made from leather so you know they will be durable and protect your feet, no matter what the weather.
They offer a more relaxed look for a sturdy and strong winter boot.
Available in size 6 to 11.