This is a subject that I’ve been banging on about for ages and it’s featured in a number of my recent articles – but I’ve never really looked at it in any great depth.

We should all know by now that good footwear is one of the lynch-pins of a great outfit. In fact, having the right shoes will dramatically change the fortunes of your entire wardrobe, so it’s important to get them right.

This is especially true during the colder months, your shoes not only need to look good but they also need to keep you on your feet. Falling over is never cool.

The Bigger The Better

It’s really quite simple: bigger is better. Big soles, bigger shoes.

Thankfully, there is a massive choice of season appropriate footwear available to you both on the high street and from the more expensive outlets. And don’t assume it’s all about hiking boots. To really make your outfits stand out this season, wearing something a little out of the ordinary could be just the thing you need.

As always, the more you can spend on your footwear the better, but don’t think of it as essential – you might find that the prefect style for you is surprisingly cheap, and we all like to grab a good bargain.

Winter Appropriate Footwear Options
1. The Brogue Boot

Men's Brogue Boots Lookbook

I’ll start with the obvious choice. We all love the brogue boot, with a pair being resident in most of our wardrobes (but not mine surprisingly) and it doesn’t take much thought to decide how to wear them. If you are already a fan, just switch your slippery leather soled boots for something with a thicker, more weather appropriate sole and you’re away.

My one piece of advice with a switch-up such as this would be to follow the shape of the boot. A thicker, bulkier boot requires thicker, bulkier clothes to match, so switch your skinny cuts for slim or straight and stick to chunky knitwear and heavy duty outerwear – my personal choice would be a colourful duffle coat, maybe in burgundy or mustard.

  • Allsaints Rok Crew JumperAllsaints Rok Crew Jumper
  • Gloverall Made In London Melton Wool Duffle CoatGloverall Made In London Melton Wool Duffle Coat
  • Topman Dark Wash Straight JeanTopman Dark Wash Straight Jean
  • Trickers Black Commando Brogue Stow BootsTrickers Black Commando Brogue Stow Boots
  • Topman Jeffrey Brogue BootTopman Jeffrey Brogue Boot
  • Kg By Kurt Geiger Alma Brogue BootsKg By Kurt Geiger Alma Brogue Boots
  • Grenson Fred Black Brogue BootsGrenson Fred Black Brogue Boots
  • Ben Sherman Movg Crepe Sole Brogue BootsBen Sherman Movg Crepe Sole Brogue Boots
  • Grenson Fred Textured-leather Brogue BootsGrenson Fred Textured-leather Brogue Boots
  • Swear Tan Leather Logan Brogue BootsSwear Tan Leather Logan Brogue Boots
2. The Crepe/Wedge Sole Brogue

Men's Crepe/Wedge Sole Brogues Lookbook

As much as we adore brogue boots, they aren’t for everyone. Some people just prefer shoes. But of course, brogues have exactly the same problem as brogue boots – those pesky leather soles.

You could, of course, simply buy a standard brogue with a thicker sole – but if you really want to make an impression, why not go for something with a crepe or wedge sole? These will give you the extra thickness you require for warmth and the extra grip you need to deal with any winter weather. Plus they also add a little touch of individuality.

I suggest you mix up your casual and formal aesthetics by pairing them with some tailored trousers or use them to modernise the heritage trend with some jeans and a tweed/herringbone blazer. Finish with a peacoat over the top.

  • Folk Standard Gingham Check Cotton ShirtFolk Standard Gingham Check Cotton Shirt
  • Customellow Brown Herringbone BlazerCustomellow Brown Herringbone Blazer
  • Allsaints Bleeker Iggy JeansAllsaints Bleeker Iggy Jeans
  • Ben Sherman Movg Crepe Sole BroguesBen Sherman Movg Crepe Sole Brogues
  • Topman Venice BrogueTopman Venice Brogue
  • Sanders Light Tan Leather Jude Gibson BroguesSanders Light Tan Leather Jude Gibson Brogues
  • Selected Homme George BroguesSelected Homme George Brogues
  • Churchs Downish Navy Tri ShoesChurchs Downish Navy Tri Shoes
  • Grenson Archie Textured-leather Wingtip BroguesGrenson Archie Textured-leather Wingtip Brogues
  • Paul Smith Shoes & Accessories Crepe-sole Leather BroguesPaul Smith Shoes & Accessories Crepe-sole Leather Brogues
3. The Hiking Boot

Men's Hiking Boots Lookbook

The hiking boot still hasn’t quite caught on – as far as I can tell – but I think this could be put down to the fact that it is a big departure from what we are all used to. Quite a few men are still holding on to their military boots a little too tight.

Whether you go for a more traditional leather style, or opt for something fresh and modern I wouldn’t go in any other direction than a masculine, rugged, outdoorsy aesthetic. Grab yourself some thick cotton/herringbone trousers or selvedge jeans, pull on a pair of boot socks, pair with a chunky roll neck or flannel shirt and throw on a parka for a cosy, winter warming outfit.

  • Universal Works Cream Soft Lambswool Aran Roll Neck KnitUniversal Works Cream Soft Lambswool Aran Roll Neck Knit
  • Denim & Supply Ralph Lauren Army ParkaDenim & Supply Ralph Lauren Army Parka
  • Reiss Gatsby Herringbone Trousers GreyReiss Gatsby Herringbone Trousers Grey
  • Fracap Coffee Suede Vibram Soled Hiking BootsFracap Coffee Suede Vibram Soled Hiking Boots
  • Boxfresh Khyke Fur Hiking BootsBoxfresh Khyke Fur Hiking Boots
  • Selected Homme Mars British Millerain Hiking BootsSelected Homme Mars British Millerain Hiking Boots
  • New Look Jack & Jones St Moritz Hiking BootNew Look Jack & Jones St Moritz Hiking Boot
  • Selected Hiker Shearling Lined BootsSelected Hiker Shearling Lined Boots
  • Diemme Roccia Vet Leather-trimmed BootsDiemme Roccia Vet Leather-trimmed Boots
  • Fracap Brown Texture Leather Commando Hiking BootsFracap Brown Texture Leather Commando Hiking Boots
4. The Worker Boot

Men's Worker Boots Lookbook

The American workwear style is huge this season, and it just so happens that it’s the perfect look for winter – what with its big textures, warm fabrics and a great palette of muted autumnal colours. It’s also really easy to wear, and you’ve probably got most of the clothes you need in your wardrobe already.

I would go all out with your layers for this kind of look. Grab some straight cut, heavy weight, stone chinos, throw a denim, flannel or cord shirt over a Henley tee, then grab a nice thick lumberjack’s jacket or over-shirt to cover it all up.

Accessorise with a (fitted) knitted beanie and some thick wool gloves and you’re ready to go.

  • Allsaints Burnett Long Sleeved HenleyAllsaints Burnett Long Sleeved Henley
  • A.p.c. Washed-chambray ShirtA.p.c. Washed-chambray Shirt
  • Asos Quilted Jacket With Pu YokeAsos Quilted Jacket With Pu Yoke
  • Ymc Tobacco Twill Tapered ChinosYmc Tobacco Twill Tapered Chinos
  • Stone Mid Size BeanieStone Mid Size Beanie
  • Polo Ralph Lauren Salisbury BootsPolo Ralph Lauren Salisbury Boots
  • Timberland Earthkeeper Rugged Plain-toe BootsTimberland Earthkeeper Rugged Plain-toe Boots
  • Allsaints Detect BootAllsaints Detect Boot
  • Asos Boots With Shearling LiningAsos Boots With Shearling Lining
  • Grenson Tan Vibram Spike Duck BootsGrenson Tan Vibram Spike Duck Boots
  • Diemme Mens Firenze Ontario Work BootDiemme Mens Firenze Ontario Work Boot
  • Quoddy Grizzly Leather And Canvas BootsQuoddy Grizzly Leather And Canvas Boots
5. The Trainer

Men's Thick Soled Trainers Lookbook

Winter is no place for our lightweight canvas plimsolls. A single thin piece of material is not a match for deep puddles, freezing winds and sudden downpours. If your style requires trainers, then it’s probably time to upgrade to something more substantial.

As much loved as they are vilified, Nike Air Max or New Balance trainers are a good choice. They are sturdy, provide superb grip and are sure to keep you on your feet – it’s all a matter of perspective. Trainers can help dress down any look and are a perfect example of just how much a pair of shoes can alter the whole aesthetic of an outfit.

Try mixing them in with some creative layering: a denim jacket under a peacoat with some chinos will be a warm and fashion-forward combination.

  • Topman Grey Marl Crew Neck TeeTopman Grey Marl Crew Neck Tee
  • Reiss Bruno Crew Sweat HeatherReiss Bruno Crew Sweat Heather
  • Allsaints Kiku Denim JacketAllsaints Kiku Denim Jacket
  • Reiss Hummingbird Double Breasted Wool Peacoat GreyReiss Hummingbird Double Breasted Wool Peacoat Grey
  • Gucci Slim-fit Corduroy TrousersGucci Slim-fit Corduroy Trousers
  • New Balance U410 TrainersNew Balance U410 Trainers
  • Nike Air Max 1 TrainersNike Air Max 1 Trainers
  • Allsaints Roc BootAllsaints Roc Boot
  • New Balance Burgundy 574 Urban Sportsman TrainersNew Balance Burgundy 574 Urban Sportsman Trainers
  • Reiss Aster High Top Trainers BitterReiss Aster High Top Trainers Bitter
  • Lanvin Suede And Patent-leather SneakersLanvin Suede And Patent-leather Sneakers
  • Armando Cabral Suede-trimmed Wool High Top SneakersArmando Cabral Suede-trimmed Wool High Top Sneakers
Final Word

Don’t get caught out by our constantly shifting weather, a decent pair of shoes will make a big difference to the overall feel of your outfit and your physical comfort – no one likes cold toes, so it’s worth getting your footwear right.

Let me know your thoughts, and which season appropriate footwear styles you will be sporting, in the comments below…