The Top 10 Most Stylish Men’s Winter Boots of 2017

The Top 10 Most Stylish Men’s Winter Boots of 2017

The Top 10 Most Stylish Men’s Winter Boots of 2017

winter boots

Winter is right around the corner (and quite possibly at your front doorstep depending on where you live).
And even though I am not a fan of it, what I am a fan of is boots. Boots are a style essential for any man, and when your toes start to freeze, there’s no better time to break them out.
What type of men’s winter boots is trending right now?
Have a look:
(BTW These winter boots are not in order from most stylish to least stylish, but instead, they go in order from least to most suitable for wintertime. It’s just easier that way, so make sure you check them all out.


I love chukkas. They are not only stylish but they are versatile as all hell.
Their only downfall, is most of the nice chukkas you will find are suede. Suede and water don’t mix, so avoid rocking suede chukkas in the rain or snow and grab a leather pair instead. But on a cold day, when you’re layering up, a nice pair of chukkas will keep your feet warm while making you look a little more distinguished. Overall they are a great winter boot for men.
We have picked out two pairs of chukkas which I totally dig, mostly the second from East Dane:
1) Dunn Cradled Tan Chukka – $95.00
dune cradled tan leather
These are a beautiful pair of chukka’s, plus they are leather which is ideal for a man’s winter boot.
2) Wolverine 1880 Julian Suede Chukkas – $155
wolverine 1880's
These bad boys are handcrafted from suede with smooth leather trim. The single-piece toe and 3-eyelet design create a versatile style. Again, while great for the cold, not great for rain or snow, being they are suede. For more options on chukkas go here.


Lace-ups are a great look. This kind of boots go great with skinnier jeans and are my personal pick for casual events. A nice pair of jeans, a t-shirt, and some lace-ups boots will put your head and shoulders above the other guys in the room. Not only are they great winter boots, but they are great any season boots for men.
3) Clae Hamiltons – $140
Clae Hamilton
In my opinion, Clae makes some of the best men’s shoes on the planet. They are my personal favorites, and I personally own 5 pairs, 3 being Hamiltons. I have had my hamilton for 2 years now, and they look better than when I bought them. Most stylish boot out there, in my opinion, hands down.
4) Wolverine 1883 Ramon 6″ Boots – $195.00
wolverine lace ups
For a more sturdy and rugged look, check out something like Wolverine 1883’s. These boots are handcrafted with pebble leather and boat a thick rubber sole. They will outlast any winter storm while keeping you looking great.

Wingtip Boots

Next up are wingtip boots. Wingtip boots are pure class, and yes – they look great in the winter, summer, spring, or fall. They can take a normal outfit and dress it up immediately and are perfect for events, dates, and formal occasions.
5) Grenson Sharp Cap Brogue Boots – $440
wing tip mens winter boots 2
These are great-looking boots. A bit pricey, but worth it in the long run.

Chelsea Boots

I’m not a fan of Chelsea’s, in fact, I have never owned a pair. But most of my good friends have, and I know a lot of guys are into them. The great thing about Chelsea’s is that they hold up in the snow and other wintery elements. Unlike chukka’s, they won’t go to ruin and still look great. They are better for guys who don’t dig the skinny jeans and want something that will go over the ankle and rest on the top of the boot.
6) H&M Leather Chelsea Boot – $99
Leather Chelsea Boot
This is our first pick of Chelsea’s, because you just can’t beat the prices at H&M. And surprisingly, they look pretty damn good.
7) Montague 1000 Mile Chelsea Boots – $290
wolverine chelsea boots
For something a little more sturdy and classy, check out these montague 100 miles chelsea boots. Or check out others like them at East Dane’s chelsea boot section.

Stylish Weather Boots

Okay, so this post is a winter 2014 boots guide. Yeah, we showed you how to look good, while protecting yourself from the elements. But what about extreme elements, like those dudes from Alaska, or for guys who like to track through the wilderness in sub-zero temperatures and still maintain a sense of style.
8) Tretorn Garde Stovel Vinter GTX Boots – $200
winter boots 1
What I love about these Treton winter boots are the sherpa interior and Gore-Tex® lining. Yeah, they have mixed leather upper with canvas insets that look awesome, but you know no matter how cold it gets your toes are staying toasty warm in these boots.
9) Tretorn Gunnar Boots – $95
winter boots 2
These are awesome-looking men’s boots that are pretty much one of the only pairs of boots I’ve found that would look awesome going to a bar in, and then would fully protect you walking through wet snow. They are lined with a rubber shell and have a fleece sock liner and rubber sole.

The I’m Shoveling Snow, But My Neighbors Hot And I Still Wanna Look Kinda Good Boots (A.K.A Duck Boots)

This last category of boots is for straight-up climbing a small mountain or shoveling snow, while still maintaining a sense of style. While most winter boots of this fashion are not built for performance, they lack style. But Sorel and Hunter have changed that.
10) Sorel Men’s Caribou Boot – $140
Sorel mens winter boots
Featuring a nubuck leather upper with waterproof construction, seam sealing and a removable ThermoPlus™ felt inner boot for warmth, comfort, and protection in any weather, these boots are a great conservative pick.
Bonus: 11) Hunter winter boots – $165
hunter mens winter boots
I linked straight to hunter’s website, instead of just one boot, because that’s how badass these men’s winter boots are. Their winter boots are built for outlasting anything, from intense rainfall to extreme winter elements. See which ones you like.

Men’s Winter Boots: Honorable Mention

There are a lot of good-looking winter boots out there for men. We could leave out a couple of brands that look great while providing awesome winter protection.

Men’s Winter Boots Honorable Mention #1

The North Face – $150.00
north face mens winter boots
The North Face makes quality winter boots and they look badass. If you are thinking of climbing Everest, and you want to do it in style, check out The North Face.

Men’s Winter Boots Honorable Mention #2

UGG’s For Men – Butte – $225.00
Ugg winter boot for men
This is an honorable mention because Uggs are kinda girly, and even this winter boot for “men” is kinda girly. But some guys might like that. So to each his own. Wear it proudly.

Men’s Winter Boots Honorable Mention #3

The Scott Derby Winter Boot – $510
the scott derby winter boot
This is a beautiful men’s boot, but the reason they are shunned to the honorable mention list is because of the whopping price tag of $510.00. Nevertheless, they deserved a shout-out.
PS. On a different, but related note, if you are into hiking, HERE and HERE you can find some excellent trekking poles!

In Conclusion

There are a lot of winter boots of out there for men. And needing them doesn’t mean you have to compromise on your look. Check out all the above brands and do some research for yourself to see what winter boots will be right for you.
And let us know your favorite brand or if you have any suggestions in the comment section below!
best winter boots for men

Let us know your thoughts in the comments below and check out some more articles you may like to continue your self improvement journey!

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0 thoughts on “The Top 10 Most Stylish Men’s Winter Boots of 2017”

  1. Hey Sean! What type of Timberland boot did you use for the first picture (title picture) of this article. I like those boots a lot, but they weren’t a part of the article itself. Thanks so much for your help!

  2. How about you answer the question everyone’s been asking Sean. Seems like you’re being kind of a d*ck right now. Either you don’t know, or your don’t give a sh*t about the comments below your article. So please be so kind to answer.

  3. Great selection as usual G!! I already own a pair of the Chilkat’s in black. I would love to own a pair of the Timberland 1978 hikers. But I may go a little cheaper and invest in a pair of Woolrich Trailstomper’s. $149 at DSW. Thoughts?


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