The Best Boots For Men 2020

Matches Fashion, Dr Martens, Danner

A great pair of boots is a necessity for every man’s winter wardrobe. The criteria to consider for a winter boot, opposed to a summer boot, is less of a sleek, narrow silhouette made from perhaps fine suede or a soft, supple Italian leather and instead, more of a chunky, welted commando sole (Vibram is always good) to help you grip to those icy pavements and a sturdy leather, made waterproof with a wax or oil coating. It’s worth considering your budget as well, as spending a little more in the winter boot category will definitely extend the shoes’ shelf life – remember, these will be saving you from all the harsh elements. You don’t need to go over the top when it comes to protection. No, steel toe caps are not necessary. You still want the boot to be stylishly versatile. A chunky boot can and should still be styled with tailoring and everything in-between. To help you be winter ready, we have found the best boots out there, so you don’t have to:

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There are big romper stomper boots. Then there are Grenson’s military-grade 14 eye boots. As one of the highest options in the Northamptonshire brand’s arsenal, they’ll easily carry you through winter. Lacing up is decidedly more difficult.

14 Eye Boot, £350,


Bottega Veneta


For a contemporary take on the Chelsea boot, Bottega Veneta adds a transparent, jelly-shoe-like sole to its chunky Chelsea boot toe, making a boot that will go well with almost any tailoring. Avoid going OTT and make the boots your statement piece.

Transparent-Sole Leather Chelsea Boots, £845,


Acne Studios


If you’re a fan of the hiking style, but not too keen on the gruelling climbs up uneven terrain, most probably in the rain, then these flatform hiking shoes by Swedish brand Acne Studios are the perfect compromise. To avoid looking too much like an outdoorsman, pair with wide leg jeans (we like white) and a chunky black knit on top. Don’t forget to protect the suede to ensure it can handle the rain.

Flatform Suede and Mesh Hiking Boots, £540,


Manolo Blahnik


If Indiana Jones had a dinner at the National History Museum. A smart vintage style strapped Chelsea boot can be a sturdy, more formal approach to your winter boot game. A nice grippy sole will help in those treacherous inner-city conditions, but the stylish silhouette means it can be paired with an outfit that needs to be taken seriously. Again, please use suede protector!

Black Vintage Suede Ankle Strap Boots, £795,




These boots look like they would survive the apocalypse, and seeing as Church’s make them, they probably will. But they also look mega. A bit rough-and-ready, but can easily be styled up, with a nice pair of black jeans, a fine gauge knit and a your favourite bomber jacket.

Coxbridge Vintage Calf & Suede Lace Up Boot, £640,


New Balance x Snow Peak


Are these boots? Yes, no, who cares? Pair them with white socks, cropped blue jeans, a white T and a chunky cardigan to achieve that I-work-in-a-startup-but-also-sometimes-holiday-in-Cornwall look. These can also be broken down to a slip-on, clog style sneaker. So in a way, these aren’t really boots at all. Oops.

New Balance Tokyo Design Studio x Snow Peak Niobium Concept 1, £280.00,


Dr Martens


A true classic in the world of boots. Moving away from the angry punks that made these boots so iconic, Dr Martens are now found in all walks of life. Push through the initial discomfort as their sturdy leather softens to the shape of your feet and you will have a boot for life. Try dressing these up, with a pair of cropped, pleated trousers and a denim jacket. Dr Martens also offer great leather treatment kits to ensure these really do last forever.

2976 Atlas Leather Chelsea Boots, £149,




The ultimate hiking boot, which so happens to also look great. Remember that winter when all trains were cancelled due to the snow? Well if that repeats itself, walking home will be a breeze in these (we don’t recommend this however). Built in Danner’s Portland factory, these boots have a Gore-Tex and Thinsulate lining and a solid AF Vibram sole. These truly are the hardiest of winter boots, fact.

Ridge Arctic Shadow 200G, £320,




A pair of rather subdued leather boots from the charismatically brilliant, Italian luxury brand, Gucci. They have a zipped side for easy access can can be styled formally, with shirts and tailoring, or take inspo from Gucci’s A/W’20 menswear collection for a more Nineties punk style.

New Arley Pebble-Grain Leather Brogue Boots, £790,


Red Wing


Red Wing named these The Roughneck as they are one of their toughest boots. Briar Oil Slick Leather and a super-strong Vibram Lug Outsole, make these the perfect boots for almost any terrain. More than enough then if the terrain you need to tackle is your office. Pair with black corduroy trousers and a denim shirt for that American Mountain Man vibe.

Roughneck Moc Toe Work Boots 8146, £269,




Blend into the grey colour pallet of the city with these sneaker-like hiking boots from ROA. These have a waterproof kudu leather blended with an insulating camouflage patterned panelling for a contemporary combat feel. Pair with any trousers by A-Cold-Wall* and a chunky roll neck.

Andreas Printed Canvas Boots, £410,

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