Dec' 2015


Practical Boots To Survive Autumn Winter

The weather has taken a turn for the worse, the rain is setting in and it seems winter is finally upon us.  If I was anything even remotely resembling a cool #menswear blogger, I’d make some awesome Game of Thrones reference about winter coming.  But I’m not, so I won’t.

But the one thing I am when it comes to men’s style is prepared, and you should be too.  Because without a good game plan heading into the colder months, you’re just setting yourself up for a mighty wet fall.

In particular, you’re going to need a wardrobe full of warm, seasonally-appropriate fabrics, a decent overcoat and, the focus of this article, a couple of pairs of boots to keep your feet protected and dry.

If you ever needed a reason to get excited about winter, this is it: it’s boot season again. Gone are the flimsy, hard to maintain/keep clean lightweight silhouettes such as boat shoes, trainers and espadrilles. Instead, it’s time to dust off the old faithfuls and jump in some (not too deep) puddles.

And that really is the best thing about boots: they can be relied on. You don’t need to worry about them once they’re on your feet. They require very little maintenance (if you invest in quality), are versatile enough to work in both casual and formal settings and can be paired with pretty much any item of clothing you already have in your wardrobe – from a pair of olive cargo trousers to a navy suit. It just comes down to what type of boot you buy…

To help you make the right decision, I’ve pulled together a list of four specific silhouettes that will see you through even the darkest of nights. I’m not saying you have to buy them all. I’m not saying you have to buy only one. All I’m saying is that these are the boots I fall back on time and time again when it comes to handling whatever this unpredictable season throws at me.

As always, it’s important to purchase shoes that fit you. You’re going to be wearing them a lot and blisters are never fun. Much like fine tailoring, you really do get what you pay for – in terms of fit, quality and craftsmanship – so always buy the best you can afford.

Look for traditionally made styles and treat your footwear as an investment. After all, a great pair of boots will last you for many, many years.

So let’s get to it, shall we?


1. Leather Chukka Boots

These are an everyday essential for me. I used to be a brown suede desert boots type of guy, but they just weren’t a sustainable option.

Suede already gets a bad rap for being a delicate material, but when it comes to a night out it really is impractical. Have you ever tried cleaning suede hungover on a Sunday? Why do it when you can avoid it?

Chukkas are near enough the exact same height, shape and size as a desert boot, but more suited to the evening, especially in black or brown leather. They can be dressed up or down effortlessly and look superb matched with dark denim, grey chinos or tweed trousers.

Just a great all-rounder.

2. Tan/Burgundy Brogue Boots

The perfect dress boot. The brogue detailing adds an element of formality to the otherwise relaxed silhouette and burgundy/tan has been every style-conscious gent’s go-to colour choice when wanting to stand out in a business environment for years.

While they work perfectly well paired with jeans and other rugged workwear items like cord shirts and leather jackets, they look particularly great teamed with traditional suiting fabrics like worsted wool, flannel and tweed.

To give your outfit an added touch of detailing, fold the hems of your trousers/chinos/jeans a couple of times. Not only does this help dress down the look slightly, but it also shows off your boot to the fullest.

For those that work in more conservative office environments, don’t worry, they will simply give off the same appearance as a brogue shoe once your suit trouser hangs over them.

3. Brown Chelsea Boots

Made a comeback last autumn/winter and if you don’t currently have a pair of Chelsea boots in your shoe collection, you’re not doing yourself any justice.

Yet rather than going down the obvious Bob Dylan/early Beatles route by investing in black leather, why not opt for a Chelsea in a shade of brown – whether that be chocolate, walnut or tan?

Combine with your navy/grey cold-weather suiting during the working week and reference their rock ‘n’ roll heritage at the weekend by pairing with slim black jeans, a plain white tee and leather biker.

Tip: Look out for burnished toe styles this year, which will add character to your boots and show you are a man who pays attention to the details.

4. Hiking Boots

Or, in simple terms, a pair of boots that you’re not afraid to get down and dirty with. Some real skull crushers, as my punk friends would say.

I love anything made by Red Wing or Wolverine but these will really come down to your own personal taste and the role they’re set to play in your wardrobe.

I have a chocolate brown pair of Wolverine 1000 Miles that I exclusively wear with worn in denim, Oxford cloth shirts and rugby tops.

Tip: Try styling with thick boot socks poking out the top in a contrast colour or pattern. They offer a great way of injecting some colour and life into your practical winter looks.


There you have it, four boots that will see you through not just this coming autumn/winter season, but many more to come.

Always remember that it’s important to take care of your footwear: shoe trees and the occasional clean and polish will do wonders in prolonging your boots’ lifespan.

But as always, I want to hear what you have to say. Did I miss a key style from the list? What boots do you turn to once the cold sets in? And which brands do you prefer?