Essential Winter Footwear

Morjas - The Hiking Boot in Brown Suede

I wish I could wear loafers all year round, and I wear them as often as I possibly can, but winter is the one season when they stay on the shelf the most. It’s often too cold for loafers, and winter also brings a lot more wet days and snow. I say this often, but I’ll say it again, a lug sole on loafers makes no sense and won’t make them any more practical in bad weather; it just makes them less stylish. A pair with a slim rubber or Dainite sole will do the job without compromising the aesthetic. On days when everything is wet or covered in snow, the only option is a solid pair of boots if you don’t want wet feet and frozen toes. And when it’s not as wet but still very cold, a nice pair of derbies should do. Here are the styles I reach for in winter, and what I think works best to stay warm, dry, and still look put together. 

So here are the styles that are most practical in winter. Some are more versatile than others, but on certain days you don’t really have much choice and have to compromise on style if you want to stay warm and dry.

Loafers

Alden - 6243F Unlined Leisure Hand Sewn Penny Loafer in Snuff Suede

I know some people will disagree, but I have no problems with loafers in the winter. Because there’s a lot of grit and salt on the streets, I recommend getting a pair with a slim rubber or Dainite sole, because it’s more durable in these conditions, plus it has better grip than leather soles, so you don’t have to worry when it’s wet. A pair of brown suede loafers is one of the most versatile shoes you can own; you can wear them with almost everything and almost all year. Leather versions have a slightly more serious appeal, although they can be dressed down as well. Loafers are also the most open style you can wear during winter, so if you want to add an extra pop of colour with socks, they’re the perfect option.

Here is my list of Best Quality Loafers at Every Price Point

Derby Shoes

Paraboot - Villandry X Centre Commercial

This is another style you can wear all year long, but it comes in even more handy during wet and colder months. Some styles are more versatile than others - those with lug soles are especially practical during winter, but if you want something a bit more elegant and dressy, go with a style that has a slimmer sole. And if you prefer a lug sole, the upper will make the difference in versatility. For example, the Paraboot Avignon can be worn with both casual outfits and tailoring, while the same can’t be said for the Paraboot Michael.

If you want to learn more about derby shoes, read this article.

Chukka Boots (also Desert Boots)

Myrqvist - Haga Chukka Boots in Dark Snuff Suede

When it comes to pairing with outfits, they’re just like suede loafers - they can be matched with almost anything, but they have a slightly different visual appeal. Usually, people who don’t like loafers prefer desert boots, or vice versa. You can wear them most of the year, although unlined versions aren’t very practical in winter since you’ll probably get cold, so for winter I would suggest looking for lined options. Personally, I try to stay away from leather soles on chukka boots since this is my alternative for loafers in bad or cold weather, but keep in mind that there’s a noticeable difference between crepe and rubber or Dainite soles in comfort and appeal. And similar to loafers, styles with rounder toeboxes are more casual than those with longer, pointier toeboxes, which can have a very formal appeal.

Here is my list of Best Quality Chukka Boots.

Chelsea Boots

R.M.Williams - Comfort Craftsman G Boot Yearling Dark Tan

Chelsea boots are probably the most versatile type of boots. The sleek, close-fitting silhouette makes them work with both tailored looks and casual outfits. You can wear them most of the year, but in winter I’d recommend lined versions to keep your feet warm, especially if you’re walking in wet or snowy conditions. Similar to chukka boots, and this goes for most footwear, rounder toes feel more casual, while pointed or elongated toes have a dressier appeal. And even though most chelsea boots come with leather soles, rubber or Dainite soles are more practical in winter. A good pair of chelsea boots will work with almost everything, but if you want a pair that looks great with a suit, avoid lug soles and go for something with a slimmer sole.

Hiking Boots

This is the ultimate form of winter footwear and what I consider the style to go for when you really don’t have any other choice - for days with the worst weather or a lot of snow. It’s also a style you can always rely on to have good grip and keep your toes dry and warm. And don’t forget, on those days thick socks make a difference!

Morjas - The Hiking Boot

All these styles are really versatile, so you could have all of them, but it will come down to where you live and what winter looks like there. Some might not even need a pair of boots, while others can’t imagine winter without them. Let me know what your most-used winter footwear is.

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