Oct' 1921


Re-Boot This Autumn, My Favourite Boots This Season

It shouldn’t take a sensational weather shift to make you realise things are going to get colder, wetter, and darker from here on out – just like every other British winter.  Rather than conform to stereotypes, and complain about the weather to anyone who’ll listen, why not get yourself prepared and invest in some key footwear for the months ahead?

Yes fellas, that means spending your hard-earned cash on some decent cold-weather kit, I’m talking heavy duty overcoats, thick-knit jumpers, and cosy scarves.  But arguably most important of all, investing in some proper winter boots to keep your feet warm and dry without compromising your overall look.

Despite those chunky soles and unforgiving leathers, winter boots are some of the most versatile shoes you can buy.  Invest in the right quality pair and they’ll last for decades to come, more economical in the long run, not to mention a more sustainable approach to buying shoes. 

It’s officially Boots O’Clock, so here’s my top picks and favourite ways to style them out:


The Classic Chelsea

When it comes to boots there are few choices as versatile and timeless as the classic Chelsea.  A reliable companion to everything from jeans to chinos, they can be easily dressed up or down based on the occasion, plus they’re pretty season-less, so you can splash out now and still be wearing them next spring.

Consider investing in a suede pair for something a little more stand out, but be sure to spray with a suede protector every time you decide to wear and it should go without saying, always check the weather forecast beforehand!

Without a doubt one of the most timeless and versatile in the shoe game and a great way of adding some colour and vibrancy to an outfit.  Get The Look:



The Desert Boot

A desert boot is arguably my most worn shoe during the transitional period we find ourselves in right now.  It’s sheer versatility means it can be worn with a plethora of trouser options not to mention it’s an extremely comfortable member of the boot family, requiring minimal wearing-in and ideal for those of you who spend a fair bit of time on your feet.

What is the  difference between a desert and chukka boot you may ask?  All desert boots are chukkas, but not all chukkas are desert boots… chukka boots originally got their name from polo, a chukka is a period of time within the game, similar to a quarter in American football.  Chukkas include two or three eye-holes and are always an ankle-high boot, it’s this structure that makes them a chukka.  Desert boots are a specific subset of chukka boots, they always have crepe rubber soles.   

Look for a pair cut from a rich chocolate-brown nubuck leather or suede, they may not be the smartest choice for wet weather, but I can’t think of many better options for a crisp autumn day. 

A pair of desert chukkas will keep your feet comfortable all day long while not compromising on your style.  Pair them with all manner of trousers, from jeans to chinos or for something a little different, a pair of cropped trousers for the ultimate smart-casual vibes.

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The Leather Lace-Up

The leather lace-up is always a safe bet when it comes to investing in a winter boot.  Timeless in design and versatile in it’s nature, a leather boot is the most weather-hardened you will find and consequently can be on the more expensive end of the spectrum.  I always justify my shoe purchases with the trusty ‘price per wear’ equation, the cost of the shoes divided by the number of times you’ll likely wear the shoes and with a pair of good quality leather boots you’ll likely wear them in the hundreds of times before they need repairing.

These oxblood brogue leather boots have the sort of timeless silhouette and hard-wearing construction that’ll ensure you’re still wearing them years from now, and they come fitted with a rubber sole, allowing you to stroll through the wet autumn leaves with ease.  Wear them with thick socks and tailored trousers and stride through London with purpose.

For a more refined take on autumn footwear, a leather lace-up boot works beautifully with tailored trousers for something rather smart or a pair of jeans with a turn up for a relaxed and  ultra casual vibe.

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The Leather Chukka

A new obsession of mine, the chukka boot comes in many forms but the leather version is my personal favourite.  Similar to the leather lace-up brogue, these are fit for any weather scenario and the rubber sole will give great grip in wetter conditions.  I’m a particular fan of wearing these with more casual outfits, jeans in particular, but they look equally at home with a pair of chinos or even tailored trousers for a smarter occasion.

For something a little different this autumn why not add a pair of leather chukkas to your shoe collection.  Just add dark selvedge denim jeans and a turn-up and you’re good to go!

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