Practical Boots To Survive Autumn/Winter

The weather has taken a turn for the worse, the rain is setting in and it seems summer is well and truly over. 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…

Top 5 Men’s Boots For AW14

To help you make the right decision, I’ve pulled together a list of five 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.

Men's Leather Chukka Boot Outfit Inspiration Lookbook

river island aw12 bellfield aw14 river island aw13 office shoes aw14 bellfield aw14
  • H By Hudson Houghton Boots In BlackH By Hudson Houghton Boots In Black
  • Asos Chukka Boots In LeatherAsos Chukka Boots In Leather
  • Asos Chukka Boots In LeatherAsos Chukka Boots In Leather
  • Dune cradled Round Toe Chukka BootsDune cradled Round Toe Chukka Boots
  • Ted Baker Torsdi Casual Ankle BootTed Baker Torsdi Casual Ankle Boot
  • River Island Brown Leather Chukka BootsRiver Island Brown Leather Chukka Boots
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.

Men's Brogue Boot Outfit Inspiration Lookbook

hugo boss aw14 j crew aw13 j crew aw14 gant rugger aw13 simons aw13 next aw14 matalan aw14 reiss aw13 lab pal zileri aw14
  • He By Mango Brogueing Leather BootsHe By Mango Brogueing Leather Boots
  • Oliver Sweeney Wren Brogue Boot BurgundyOliver Sweeney Wren Brogue Boot Burgundy
  • Okeeffe Felix Leather Brogue BootOkeeffe Felix Leather Brogue Boot
  • Grenson Sharp Leather Brogue BootsGrenson Sharp Leather Brogue Boots
  • Redwick Leather Brogue BootRedwick Leather Brogue Boot
  • Bertie calibrate Lace Up Brogue BootsBertie calibrate Lace Up Brogue Boots
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.

Men's Brown Leather Chelsea Boots Outfit Inspiration Lookbook

Massimo Dutti zara editions 2013 allsaints aw12 hugo boss aw14 BRAX aw14 the kooples aw13 tommy hilfiger sportswear aw14 reiss aw14 lab pal zileri aw14
  • Selected Homme Marc Chelsea Boots In BrownSelected Homme Marc Chelsea Boots In Brown
  • Rolando Sturlini Leather Chelsea BootsRolando Sturlini Leather Chelsea Boots
  • Asos Chelsea Boots In LeatherAsos Chelsea Boots In Leather
  • River Island Brown High Shine Buffed Chelsea BootsRiver Island Brown High Shine Buffed Chelsea Boots
  • River Island Brown Buffed Chelsea BootsRiver Island Brown Buffed Chelsea Boots
  • Bertie Clapham Common-chelsea BootBertie Clapham Common-chelsea Boot
4. Duck Boots

Perfect for those days when you have to deal with torrential rain, sleet or snow.

Traditionally they come with brown rubber bottoms and olive leather uppers, but modern iterations are being produced in a variety of colours and styles.

They are probably the most comfortable shoes I’ve ever worn and a personal favourite due to their slightly more interesting shape and history in comparison to the Wellington.

Pair with heavy duty twill chinos, denim shirts, tweed blazers and quilted jackets for the ultimate town meets country look.

Men's Duck Boots Outfit Inspiration Lookbook

ted baker aw12 unknown
  • J. Crew Lacrosse For J.crew Duck BootsJ. Crew Lacrosse For J.crew Duck Boots
  • Sperry Eva Duck Boot ShoesSperry Eva Duck Boot Shoes
  • Nashoba Summit Black Suede Mens Casual BootsNashoba Summit Black Suede Mens Casual Boots
  • Traibreaker Duck Bt WpTraibreaker Duck Bt Wp
  • Sorel Ankeny – Lace-up Boots – BrownSorel Ankeny - Lace-up Boots - Brown
  • Sorel Winter Boots – BrownSorel Winter Boots - Brown
5. 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.

Men's Hiking Boots Outfit Inspiration Lookbook

penfield aw13 suitsupply aw13 louis vuitton pre aw13 he by mango fall 2014 j lindeberg aw12 simons aw13 espionage aw12 Woolrich John Rich & Bros aw13 closed denim aw11
  • Bellfield Hiking BootBellfield Hiking Boot
  • The North Face Mens Ballard 6 Inch Black Mountain BlueThe North Face Mens Ballard 6 Inch Black Mountain Blue
  • Mens Jules B Shearling Lined Hiking BootsMens Jules B Shearling Lined Hiking Boots
  • Brasher Hillwalker Ii Gtx Mens Hiking BootsBrasher Hillwalker Ii Gtx Mens Hiking Boots
  • Sorel Mad Mukluk – Lace-up Boots – BrownSorel Mad Mukluk - Lace-up Boots - Brown
  • He By Mango Leather Worker BootsHe By Mango Leather Worker Boots
Final Word

There you have it, five 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?

Let me know in the comments section below…

Matt Allinson


  1. Bought a pair of black chukka boots last autumn and I can tell you, all of what’s written here is a complete truth. I’m hoping to find a nice pair of burgundy brogue boots this year to give myself a couple of more options and to keep my chukkas in good condition for at least a couple of years more.

  2. Great article as always – I’ve just purchased some Dr Martens Affleck boots, I appreciate the stigma they carry but I’m already loving them and they look great – they’ll last forever too!

  3. I’ve been looking for some brown leather chukka boots but I can’t seem to find the right pair. And when I do find the right pair (something like those from rivers Island, bottom row right) I fall between two sizes. One size too tight, next too loose. Very frustrating.

    • Looks like Timberland to me. Can’t go wrong with a great Timberland. I own the same pari in a light gray.

  4. If someone could recommend me some quality non-leather, non-suede (basically not from an animal) boots then I would be immensely grateful! I realise this is an immensely difficult task though.

    • Keen makes a great synthetic boot. I’m not sure what they called them, but they are basically a duck boot. I Owned a pair for five or six years, and they were perfect for cold, wet weather! Very light weight also.

  5. What colour are those timberland boots in the headline picture? I am on their website now and I can’t find them :( Help

  6. Can anyone tell me if those Chukka Boots or the Chelsea Boots are good to go on a very cold weather?
    I mean..those kinda of boots can handle some snow?

  7. A second request for some ethical, non-animal, non-leather, non-suede, boots… There must be some out there…


  8. I’m eyeing those Brogues boots.. But what do you think if it’s in dark blue / navy colour instead of tan/ burgundy?

  9. To the people asking about vegie options for boots, Wills seems to have some nice chukka and chelsea boots in, and Vegetarian Shoes do some duck boots

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