Winter Boots For Men

How To Choose The Best Men’s Winter Boots

With the seasons starting to change, so do the trends. Some days are warmer than others, yet there’s often still a chill in the air. So the burning question remains, what to wear during the transition?!
It’s tough enough to put together the right look for you each morning, but when it comes totransitional seasons, it only gets tougher. Until now. And where are we going to start? Of course, with the footwear!

Winter boots for men are often thought of as a winter-only sartorial choice, but not any longer. Boots can be the perfect addition to both a formal or casual look and dressed down without a covered sleeve, is just the look you need for now.

We’ve picked out five of the hottest styles available to buy now! We know how we’d style them, but how will you?

The Paul Smith Falconer Chelsea 

Paul Smith winter boots for men

Starting off to ease you in has to be the Paul Smith Falconer. Who doesn’t love a chelsea boot and especially one as simple and sleek at this one?!

The suede pretty much guarantees a comfortable ride and will look at ease on foot even on a warmer day – perfect for the transitional seasons and to make it feel like less of a winter shoe!

In black or brown, we’ve recommended the brown for more of an everyday look to style with chinos, denim or a smarter trouser.

The Louboutin Antonio Calf

 Louboutin Antonio Leather Calf winter boots for menA staple shoe in any men’s wardrobe, how could we not include a little some thing from the kind of footwear himself – Christian Louboutin. Definitely for your more smarter days, the Louboutin Antonio is the perfect men’s winter boot.

Made from calf’s leather, comfort and quality is guaranteed. Available in both black and cognac, we’ve opted for the cognac for a little edge and a much warmer feel.

Perfect for a killer look to show you mean business or even your Sunday best, the hand painted boot screams craftsmanship and has just that right image you need in men’s fashion.

The Kurt Geiger Denton

Kurt Geiger Denton leather winter boots for men

If you’re looking for more of an everyday winter boot, you’ll want to look no more than Kurt Geiger. We’re in love with the casual come chic shoe that is the Denton. In a matte grained leather, you’ll not look out of place sporting them with jeans or a casual cotton.

Much more than a simple, all black chelsea boot, the Denton has a little edge. We’re definitely expecting this one to be worn everywhere from Fall to Spring. And surely you can see why!

The H by Hudson Swathmore

H by Hudson Swathmore winter boots for men

For something a lot more casual, and we all have these days – think brunch, weekends browsing around and breaks away, H by Hudson have got it right with their Swathmore boot. In a distressed black design and with a rustic feel, these boots are the ultimate accessory to dress up denim and dress down a smarter pair – think chinos or slacks.

 The worn leather look and styled lace up detailing gives you style as well as comfort – just what you need from your attire during casual occasions. Who wants to walk for hours and bear painful feet, we don’t know!

 Dubbed for ‘off duty style’ we know these will be a winner for you as well as us!!

 The Ted Baker Kiddie

Ted Baker Kiddie winter boots for men

 And finally, we had to finish with a little Ted Baker didn’t we? We all love a good desert boot, but Ted’s done it differently. If it wasn’t enough to be conformable and stylish, just like the Swathmore.

Ted’s added a little sass on top.

 Desert boots have always been unbelievably comfortable and now the brogue detailing means they’ll look great worn with, well, pretty much anything. Wouldn’t you agree?

Even the blue trim is perfect for a little something extra and takes away from the plainness of a standard desert boot. We know we’re on to a winner with this one.

There’s definitely some level of variety, yet some of sameness, among our selections but with boots, there’s always going to be. But, you can guarantee there’s a whole lot of style and something for any occasion covered.

Brrr, winter has officially knocked on the door and that makes it time to finally break out the boots. Or, in case you need to pick up a new pair, we’re going to introduce you to something a bit stylish but classic.

We believe in diversity and a well-made pair of winter boots for men like we’re about to show you will make a perfect accessory to any wardrobe

Enter Wingtip Brogues

Winter boots for men - Wingtip Brogues

Just as Desert Boots and low/high rise Chelseas are staples, nothing can compare to a sturdy pair of Brogues or Wingtips. The dress shoe nature coupled with a four seasons-appropriate look make them sturdy year-round footwear allowing a multitude of ways to wear them, which only increases their ‘style’ value.

While both of these shoe styles have climate appropriate summer-oriented counterparts, winter versions are also available; they look virtually identical, except the taller shoe goes up past your ankle, similar to Chelseas.

The main difference is the cowboy-esque designs stitched in that can be either dressed up or dressed down, making them versatile (and therefore more wearable than other types of boots). I personally own a dark pair with a slightly flat brown finish I wear with jeans. You could go sporty and cuff or roll up the pant leg as you see fit. Maybe lace up your wingtip brogues with a pair of chinos or a suit if you prefer business casual.

If you’re looking for a tough guy rugged effect… the fat yellow laces and tall lacing rings bring home the bacon. Go ahead and spend the couple of extra benjamins and purchase genuine leather. Leather is organic – it’s meant to change, unlike more synthetic materials that only buckles under pressure. Plus, leather is far more resistant and more adaptable to daily wear and tear.

Trust me on this one.

The look is absolutely worth it, especially considering how much longer they are going to last. Depending on how well you care for the leather (waterproofing in winter really helps them age, as opposed to drying the leather out. Once it cracks, it’s game over.), they will gain a slightly worn, contoured look. Remember to use those shoe trees, though.

Proper leather conditioning helps them grab and hug your feet almost like they’re custom made just for you, plus the waterproofing finish adds to their ruggedness … Think along the lines of how raw cut denim fades and stretches over time – these boots will do the same after they get broke in.

With a pair Wingtip/Brogues, you really can’t go wrong especially with quality leather … they offer a versatile and durable staple look. Guaranteed to last you for years.

Keep in mind, the genuine leather models are going to cost you some money, however you probably won’t have to worry about going to a cobbler. Chances are the respective company you choose to buy from, being on the higher end, will use hand stitching (a big plus) as well as rubber soles, an upgrade we highly recommend to get the maximum life out of your investment.

Wingtip Brogues are expensive, but have a lot to offer and can be called on to get the job done.

Heck, you may even want start growing a beard and chop wood. Chopping wood is (literally) one of my favorite workouts. We own about an acre of woods behind my house and I’m in the middle of a 3 year process of clearing it all out…

… by hand.

Last but not Least…

You might not be stalking down a raging bull elk in full rut, or stomping around the swamp with a 12 gauge cradled in your arm calling for mallards.

But that doesn’t mean you can’t enjoy their manly look and charm of a pair of Duck Boots.

Duck Boots were born, as you can imagine, to keep a hunter’s feet dry while sitting perfectly still in freezing cold duck blind. However, that doesn’t mean you can’t take advantage of their toughness for of your own workday, even if that implies a cubicle/office-esque setting.

Sometimes the sharp contrast in colors can make them hard to pair with the rest of your wardrobe. Which is why I wouldn’t recommend them unless you already own clothing in earthy tones. (If you need help with matching or want to try out camo, check it out here.)

Winter boots for men - Duck Boots


In short, there really isn’t a right (or wrong) answer when you go shopping for winter boots for men. The entire process is very personal. Being more of an accessory, the style you seek has to compliment your own wardrobe. Go here if you want to sign up for a consultation.

Remember, when it comes to boots, you get what you pay for. As another mantra of Kinowear, the price usually reflect the quality and durability. It may be easier to hit a department store clearance aisle, but those boots won’t last a year, plus they look cheap. We can help you same up to 50% if you know which stores to shop at, so check out the Kinowear Bible.

Which style gets you all hot & bothered?

Make sure you leave a comment below and let us know!

  • J says:

    I agree with the comments around the desert boot being accessable. Personally I find a shoe with actents to be gaudy and harder to pair with a well executed outfit. I think a shoe that is understated in terms of contrast goes with more parts of the outfit reularly. That said, I don’t want to say I haven’t seen a nice boot and undershirt turn heads, but in an article about cold weather thus more layers it becomes harder to create a unique outfit that is wearable day after day.

  • erlend says:

    What are some good tips for choosing a winter shoe considering height and weight when I’m about 170 cm and 70 kg?

  • Sam says:

    Ugg shortie classic boots forever!

  • Kinowear Staff says:

    They’re comfortable but not the look we’re going for. Thanks for your comment.

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