By now if you haven’t noticed the change in weather, I can officially say you’re not from this planet. Rain seems to elude us because some of you continue wearing your loafers and boatshoes in an attempt to cling onto summer for dear life. When the rain does decide to make an appearance, I hope your winter boots are ready to come out and take a beating from the winter elements.

I like being prepared for winter and I also like preparing others, which is the very same reason why I wrote this article. Having the right footwear this winter won’t just keep you looking good, cause being stylish has become a full-time job, it’ll stop you from ruining your none winter shoes and having to purchase new shoes because of the winter knocks your shoes have to withstand.

If you’re planning on keeping dry and warm this season you’re going to need a wardrobe full of warm, seasonally-appropriate fabrics, a decent overcoat (see the 5 A/W15 ESSENTIALS FOR MEN article) and, the focus of this article, a couple of winter boots to keep your feet protected and dry.

And with that, let me present to you my selection of this season’s must have winter boots.

1. The Chelsea Boot

Don’t try to justify your reason for not having a pair of these winter boots in your wardrobe. Do me and yourself a favour and go out and buy a pair of Chelsea boots. Buy them in a deep brown tan or any shade of brown for that matter and you’re all set. Go for black if you’re going for an all black look this season.

I love the pairing of black skinny jeans and this boot, especially if it’s in a brown shade (preference) they work in harmony together and so also they go well with grey chinos. Get yours at Woolworths

winter boots

Woolworths Chelsea Boot

2. The Chukka/Ankle Boot

If you know me you’ll know that I love the desert boot and it was that same love that led me to loving the Chukka/Ankle boot. I featured the Chukka boot in the ‘5 A/W15 ESSENTIALS FOR MEN‘ article and I’ll reiterate, yet again, on why this is probably my favourite winter boot.

The Chukka is the exact same shape and height of a desert boot but the Chukka comes in leather instead of suede because,let’s face it, no one wants to be cleaning suede only for the rain and mud to mess it up again. But the Chukka doesn’t just beat out the desert boot in the “looking after” department. It does daywear and nightwear brilliantly especially if it’s in black. It’s an all-rounder to me. 

Get yours at Woolworths and pair it with a pair of dark denims.

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Woolworths Chukka/Ankle Boot

3. The Brown Brogue Boot

The most formal winter boot in this selection. It’s the perfect dress boot and the brogue detailing adds that formality element you may crave if the occasion presses you to suit up and the weather isn’t in your favour. When your inner gentleman calls but you don’t want to seem serious, pair them with jeans,chinos or trousers and fold the hems of your pants, this will soften your look.

Get a pair at Woolworths

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Woolworths Leather Brogue Boot

4. The Worker Boot

This is a boot you don’t mind getting down and dirty with. You don’t mind racing through a puddle of whatever with it because it was made for that. We all need this winter boot in our wardrobe especially if you’re a person who looks the nightlife. You’ll spill just about anything on it and when all is said and done , a wipe down will restore them to being good as new.

Pair them with thick socks and jeans and tackle life. Remember, let the thick socks show here.

Get a pair at Old Khaki or Woolworths.

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Woolworths Leather Lace Up Boot


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Caterpillar Harold Men’s Boot @ Old Khakhi



This selection of winter boots should see you through winter with ease. I strongly advise any man reading this article to invest in at least a pair of boots and it doesn’t necessarily have to be these ones. Shop around and find a style of  winter boots you want,boots that compliment you and your  wardrobe.

About the Author

Sabelo Myeni
Law student. Arsenal supporter. Minimalist . Fashion. Foodie. Tea and coffee drinker


  1. Hi

    I am looking for Caterpillar Chelsea Boots. Where can i get them?

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