The winter boots guide

Even though I'm sure you love your sneakers, some shoes might be much more comfortable and convenient in winter. If you don't believe me, try it, and fabulous winter boots will convince you in no time.

That being said, it can be chukka shoes (although these I wouldn't choose when it's freezing), boots (these are great when freezing), Chelsea or another type of higher shoes or shoes with rugged soles at least.

And yes, they are not only country-friendly but also city-friendly. Let me explain to you more. The thicker sole does an excellent job, isolating you from freezing ground, like a down jacket from cold wind. And higher boots (with combination with socks suitable for winter weather, obviously) the very same job.

Before I show what I wear most often in winter, I've heard what worries some men regarding this subject. According to them, some shoes are too "stiff" or "hard", and it is not easy to walk them often so the leather could become softer and shoes more wearable.

This situation may happen the same as with loafers or sneakers. Every pair of shoes are stiff from the beginning, some less some more. There is an exception for that; it is on my waiting list of things to post, so keep waiting for that one. However, don't be frightened. My new Berwicks were a bit tougher, but after two or three days, they are alright.

Boots do have a great range of garments you can wear them with, meaning they are versatile. With chinos? Check. With flannel winter trousers? Check. Winter suits? Check. And I could go on and on.

Some days ago, I switched for sneakers for a short walk outside (it is snow here and around 0 to -3 Celsius in Prague) and the difference was huge.

In regards to that, one of my friends is claiming that you don't need winter shoes when living in the city. Still, I find that not right, at least not entirely. Winter shoes will make your life much easier through winter months even in the city. Not to mention they look great and stylish if you know what to wear with them.

Wearing Massimo Dutti brogue boots, Tommy Hilfiger white chinos, Colhay’s shawl collar cardigan and Pietro Filipi blue coat. Ph.: Petr Honc

Black brogue shoes 

Some menswear enthusiasts would say that brown is the most versatile colour for boots. But in winter, I end up wearing these black boots much more often. Even in a situation, I could go for brown as well.

Easy to combine, with grey, navy, white or colourful trousers. I wouldn't wear them with brown trousers though. They look marvellous with burgundy trousers, especially when freshly waxed and polished.

Pictured Berwick brogue shoes in country calf with Brooks Brothers burgundy chinos. Ph.: Petr Honc

Brown shoes in a country calf

Shoes like this, I wanted for a long time. The country calf should usually be a full-grain leather where makers didn't remove the top layer. A great piece for dress down suit or separates. 

Chinos with a shirt and sweater are its best friends. And whether wearing coats, Barbour jacket or whatever different kind of jacket, there is like a 90% chance you won't be wrong with these shoes.

Berwick tan Chelsea boots with jeans (sorry, forgot what are these as I no longer have them). Ph.: Mischa Babel

Chelsea boots

If you never own before Chelsea boots, once you've tried it, there's no way back. Mostly because there are no laces, you put the shoe on or off within 3 seconds.

Only be careful about the sole. Some brands make this type of shoes with the thin sole that is not suitable for freezing temperatures. It is because musicians and celebrities are wearing them in warmer days as well.

Decide for what purpose you want them and mind details like to sole.

Dark brown suede chukka shoes by czech brand Blazek, Massimo Dutti navy chinos. Ph.: Mischa Babel

Chukka shoes - not only for winter

Chukka boots are ideal for the cold beginning of spring or in autumn. Even if many people are wearing them in winter, I am not a fan. If then with thicker socks at least.

Chukka boots are traditionally not insulated, it is pure leather, which for some reason seems to be thinner than with boots to me. But this may be subjective.

Berwick double-monks with thicker rubber sole. Courtesy of my photographer Petr Honc (his shoes)

Shoes with the higher sole

Some derby or double-monk can be with a higher sole that is more robust or rugged. This can bring the comfort of classic shoes with better insulation from the frozen ground.

Also, if you don't like how boots look with formal trousers or suit, this could be the way out of it.


As a complement, I would like to remind you that you must wear boots or shoes with adequate socks for your comfort and warm to work. To help you with this, find here my comprehensive guide on socks.



Once again, thank you for reading my blog.

Yours Sincerely,

Denis