8 best men’s boots that are warm, supportive and easy to break in

Best: For durability

Rating: 10/10

Don’t be fooled by its name: there’s nothing “light” about this absolute beast of a boot from Danner. A traditional hiker with a bombproof build, this commando-soled classic has been handmade in the USA since the 1970s, and the quality is second to none. It’s also surprisingly comfortable right out of the box when compared with similar boots we’ve tested that needed a lot of breaking in.

Yes, £360 is a lot of money. However, with these boots you’re going to see an excellent return on your investment over the years. They’re built to last, which means you won’t be replacing them for a long time. In fact, you might not even need to at all, as Danner offers a full recrafting service to bring even the most battered of boots back to life.

Sizing is our one and only gripe. These boots fit big – we had to go down a full size for the perfect fit and we’d recommend you do the same.

Best: Alternative chukka boot

Rating: 9/10

British brand Yogi first emerged back in the Nineties and became popular within the Britpop movement. None other than Liam Gallagher proclaimed the Portuguese-made shoes to be “f****** BIBLICAL” on Twitter, and we’d be hard pressed to disagree with him where this laid-back suede chukka boot is concerned.

Made in collaboration with Manchester’s Hikerdelic, the Derek boot features a lovely, floppy suede upper with a moc-stitched toe, crepe sole and leather laces. It’s a relaxed-looking boot that lends itself nicely to soft tailoring, loose-fitting trousers and tactile winter fabrics such as cord, heavy wool and fleece. Thanks to the soft upper, it’s also super comfortable and perfect for pounding city streets during the colder months.

Best: Chelsea boot

Rating: 9/10

A good pair of Chelsea boots is a must in any stylish man’s winter footwear rotation, and they don’t come any better than this. Handmade in Australia by historic boot brand RM Williams, this upscale elasticated leather boot somehow manages to be elegant and rugged all at the same time. It’s smart enough to wear with tailoring, but the robust commando sole means it won’t give up the ghost on wet, slippery ground.

It’s the details that make this boot such a winner in our eyes. Everything from the stitching of the uppers to the layered construction of the heel unit is highly refined and beautifully executed. Plus, the storm-welt construction (how the upper and sole are stitched together) means it’s well suited to the unpredictable UK weather. Comfort-wise, we have no complaints either. The boots fit true to size and were easy to wear from the minute we pulled them on.

Best: For comfort and style

Rating: 9/10

The Clarks wallabee is a footwear icon that’s been imitated a thousand times. The original is still the best, and this slightly loftier version is perfect for tackling autumn and winter in style. It features a soft suede upper, a crepe sole and a moccasin-like construction with a pronounced stitched toe.

The wallabee boot is a great-looking piece of footwear that’s highly versatile in terms of styling – particularly, we feel, in this neutral “maple suede” colourway. Outside of its appearance, the thing that makes the wallabee boot stand above the competition is the comfort. It feels almost like a trainer on the foot, and that’s no exaggeration. It’s the comfiest boot on this list by far and requires absolutely no breaking in whatsoever. If you’re looking for something easy to wear that goes with everything and won’t go out of fashion, there are precious few boots better suited to the task.

Best: For active lifestyles

Rating: 9/10

This sporty option from Adidas is tricky to pin down. Is it a boot? Is it a high-top trainer? After wearing it extensively for several weeks, we’re still not certain, but one thing’s for sure: whatever it is, we love it.

Sat on top of Adidas’ signature boost sole, the free hiker gtx is extremely comfortable and cloud-like to walk in. The slip-on design means it really hugs your ankles for support, and the rigid cup to the heel provides further stability. It’s also completely waterproof, thanks to the Gore-Tex uppers, which rainwater beads off in a very satisfying manner.

It’s somewhere between a modern hiking boot and a trainer, making it great for urban use in the winter, but also for active pursuits in the great outdoors. If you’re looking for a comfortable, sporty winter boot that can do it all, this is your best bet.

Best: Winter boot

Rating: 9/10

Big, yellow, waterproof and hard as nails – if there’s any boot better suited to stomping its way through winter, we haven’t encountered it. It’s no wonder Timberland’s famous 6in boot has become the footwear of choice for everyone from labourers to rap royalty over the decades.

What we have here is quite possibly the ultimate casual boot, a boot that so many other brands have tried and failed to emulate. From the heavy commando sole to the thick leather uppers, everything about the 6in boot has been done with durability in mind. It’s built to take a beating and look the part while doing it, and, in our experience, it manages both extremely well.

We found them to be comfortable yet sturdy, and we love the gusseted tongue design that works together with the waterproof uppers to keep your feet warm and dry, whatever the weather.

Best: For versatility

Rating: 9/10

The desert boot by Clarks has remained largely unchanged for more than half a century. It’s a timeless boot that’s very difficult to fault, but one common gripe is that the crepe rubber sole can make it a little slippy when walking on wet surfaces.

This subtly updated version does away with the trademark crepe sole in favour of a commando sole with pronounced lugs. It retains all of the understated appeal and versatility of the original, but is much better suited to the autumn and winter weather.

It’s just as comfortable too. We found the desert rock to be easy to wear straight away, with no breaking in period at all. We’d suggest buying these if you like the pared-back style of the original Clarks desert boot but want something that’s more suitable for winter.

Best: Chukka boot

Rating: 9/10

This simple chukka boot from American loafer stalwart GH Bass was our best buy last year and we’re still big fans of its laid-back looks and comfortable fit. It’s made from soft, tumbled leather and sits atop a spongy rubber sole for comfort.

We simply love how this boot looks. The contrast of the upper and the sole is crisp and clean, and it goes perfectly with anything from soft tailoring to jeans. It makes an excellent “everyday” boot – the sort of thing you can just throw on with whatever you’re wearing, safe in the knowledge it’ll work.