Best Men’s Winter Boots | 2020

There is one single category of footwear every man should have in their wardrobe when we hit the end of the year and that is a winter boot.

It is inevitable that over the coming months that as the temperature drops we will also be faced with wind, rain and even potentially snow. Your box-fresh white trainers will not be up to the job. So, pack those pearly whites away until spring, its time for the big guns to come out to play.

The transition of winter boots into the mainstream menswear market has grown from our requirement for footwear that can withstand a variety of weather. Winter boots as we know them were initially designed for men that needed heavy-duty footwear that offered warmth, grip and robust ankle support in work environments. Now through lighter soles and advancements in construction, we can utilise that worker-style boot for our everyday enjoyment.

This list covers the very best winter boots currently on the market for men. From a host of different brands, they have one thing in common. That is their technical ability to handle anything that mother nature throws at them.

Grenson Bobby

The historic British shoemakers have been creating the finest footwear since 1866. So, they know a thing or two about crafting shoes that will equip you against the harsh elements of winter.

A twist on the traditional hiker boot, Grenson have gone for a rugged suede upper. It is a distinctive boot that easily marries style and function to deliver a shoe that you won’t want to take off. Luckily for you, it has padded ankle support and a lightweight wedge sole for comfort.

Timberland Stormbuck Chelsea Boot

These rugged Stormbuck Chelsea boots from Timberland are engineered from premium burnished waterproof full-grain leather.

Timberland is a brand that has made their name in providing workers of the world with heavy-duty footwear that they can rely on. The Stormbuck boot is no different. The robust uppers are combined with additional anti-fatigue comfort technology to cushion the feet for all-day comfort.

Brunello Cucinelli Suede Desert Boots

Combining the hard-wearing durability of the finest Chelsea boots with the mastery of Italian manufacturing, are these offerings from Brunello Cucinelli.

Of course, they are made on Italian shores using the finest suede. They are also equipped with rubber lug soles to handle anything underfoot.

Make sure you used suede protector before use as there is nothing that can ruin suede quicker than an impromptu downpour.

Kingsman + George Cleverley Taron

Partnering with expert British shoemakers, Mr Porter has enlisted George Cleverley to create these exclusive lace-up boots for their Kingsman range.

Constructed from tactile roughout leather on top, the Taron boot is rugged but refined. This makes it expertly adept at being worn with both smart and casual attire.


Ludwig has been honing their shoemaking skills for over 100 years. The result is some of the finest boots on the market.

Made with premium materials in their own Vienna factory, these boots will age beautifully over time. The Hunting Ankle Boot is Goodyear welted on Tuscany lasts and have added comfort from a leather lining and black crepe sole.

M Moustache Pull-Up Brown Benjamin

A Parisian brand that creates its footwear in Portugal, this is a boot full of European flair.

M Moustache prides itself in reinterpreting trending styles. Taking elements that are on-trend but making footwear timeless so as to create more sustainable pieces that will last for years.

This elegant boot is made using traditional techniques to ensure they are sturdy and durable for the long winter days.

UGG Biltmore Workboot

This is a boot that delivers on function and fashion with aplomb. From the comfort system insole to the rubber outsole it is packed full of UGG’s footwear technology.

Made from full-grain leather it has a textile lining and padded microfiber collar to add comfort and stop any uncomfortable rubbing from the leather.

Russel & Bromley Wolcott

For those men that like a less restrictive boot, this ankle version of a traditional hiker boot is a great choice.

Crafted from calf-leather with a comfy, durable sole. It is a luxurious option in a style that can be easily dressed up or down dependent on the occasion.

Fitflop Odyn

Looks like a boot but feels like a trainer.

The guys at Fitflop have harnessed their comfort technology and injected it into the world of boots. Their sole tech delivers enhanced cushioning with a contoured footbed. The result is a classic brogue style boot that has sneaker-like comfort concealed inside it. Perfect for those long winter walks.

Monterry Shearling Stonehenge

Monterry, the Paris brand, are purveyors of a slowed down menswear cycle of production. As a brand that only creates one shoe per season, they need to make it a beaut.

With shearling inside for extra-level warmth, the Stonehenge boot may sound British, but it has been handmade in Italy. This is a winter book that will easily take you from office to mountainside without falter.

Christian Louboutin Trapman

With a military aesthetic, the Trapman boot is bang-on the current utilitarian trend in menswear.

On the sole is the familiar Louboutin flash of red while there is ribbed ankle support for additional comfort.

Price-wise, this isn’t for the faint-hearted. The boot has been crafted in Italy using the finest calf leather.

Grenson Brady

How could I resist including a piece of footwear that has my name attached? But, the coincidental naming aside, these are chunky hiker boots that are built to last.

Over time any wear or tear on the leather can be treated with oil to get the boot back to its original glory. Sturdy, but with a lightweight sole, the Brady boot will become your go-to footwear for many more winters to come.

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