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Top Rated Men’s Autumn/Winter Boots

By October 27, 2020 November 9th, 2020 No Comments
Black Leather Chelsea Boots with s light heel, brown interior and elasticated sides to aid in putting on the shoes.

October is here, and with it comes our journal on the best men’s autumn/ winter boots. As the days grow colder and nights draw in, we’re forced to retire our summer wardrobes for the foreseeable future. Tops soon turn into long sleeve t-shirts, sweatshirts are taken from the back of the cupboard, and your trusty seasonal boots make their annual appearance once again.

Being barbers, we like to think we know a thing or two about comfort and durability when it comes to footwear, and earlier this year, our post on Martel + Ram was a popular read. In keeping with the shoe theme, today we’re going through our top 5 Autumn/ Winter boots here at Gents of London Barbershop.

So, whether you’re searching for the perfect boot to crunch that crispy autumn leaf in, or something comfortable and stylish to aid the walk around the inevitable Christmas market, we’ve got you covered.


The first pick on our list is one of our personal favourites, Red Wing. Red Wing originated in America over 100 years ago and supplied shoes to the US military in both world wars. These boots are something else, and the versatility of this company is second to none. A quick scroll through their website and you’ll soon see the variety of shoes and boots they offer, one which could be worn by significant London businessmen, and another which would seem quite at home on a lumberjack.

Perhaps their most popular series, the ‘Iron Ranger‘ boots, come in at a very respectable £289 and come with more than enough versatility to pair with any of your favourite autumnal looks.


Grenson boots date back to 1866 when William Green first created the company in Northamptonshire. British soldiers and the allied forces used, much the same as Red Wing, boots made by Grenson during the first and second world war. Offering a wide variety of different shoes and boots, this company has kept up with the times. Still, however, they offer quality and style you can only imagine has come straight from the 1800s.

Their ‘Declan‘ series of boots is a collection of some perfect Chelsea boots, and these would not look out of place in a business meeting at work, or the works Christmas party (very versatile, no?).


The company Wolverine were founded in Michigan in the USA way back in 1883. Wolverine supply boots for the man who is looking for heavy-duty, the man who is looking to hike and hunt, and the everyday man. With over 100 years of experience, they’re a more than reliable autumn edition to your shoe rack.

Wolverine’s ‘Dublin‘ boot is waterproof, and perfect for those who are more into long chilly walks around the countryside as opposed to a cup of tea by the fire.


You cannot compile a list of the best boots without adding in Dr. Martens. Dr. Martens, or DM’s as you’ll often hear them abbreviated to, were first introduced unto the world back in 1947. Known mainly for their status as a piece of quintessential grunge fashion, these boots have left a mark on pop culture as we know it.

Perhaps their most popular boot is their 1460 series, but you don’t even need to see a picture to know which boots I speak of. These are perfect for those dark spooky Halloween nights. The black pair are a welcome and stylish addition to any autumnal look.


Last but not least, and perhaps the most high-street-friendly brand you’ll find on our list, is Clarks. Clarks have been kicking around since 1825. A truly British institution, their boots stand the test of time. If you pop in on your next visit out, I promise you will find more than just kids school shoes.

A personal favourite of theirs is the Batcombe Lord style; a new take on the traditional brogue. These are perfect for adding that extra stylish flair to your wintry outfit. Pairing these with clothes of dark autumnal colours will have you the talk of the party.

And there you have it! Gents of London‘s best men’s winter autumn boots. Now you’re ready to take on what is arguably the trendiest season of the year. So, grab that overcoat back out from the wardrobe, get your colour schemes sorted, and treat yourself to a pair of boots from one of the fine retailers on this list.

Words by Ben Wyatt.