Whilst winter boots are obligatory in many places around the world, they don’t have to be garish and ugly things. Sometimes we want to even wear the necessities with a touch of flair and the same principles can be applied to winter boots.

After scouring high and low, we’ve found the best and Most Stylish Winter Boots For Men that you can buy online:

  1. Dressy Winter Boot: Morjas Alpine Boot
  2. Blucher Boot: Ross & Snow Riccardo
  3. Blucher Boot: Johnston & Murphy Shearling
  4. Wingtip Boot: Allen Edmonds Dalton
  5. Blucher Boot: Wolverine 1000 Mile
  6. Moc-Toe Boot: Irish Setter Wingshooter 808
  7. Work Boot: Danner Bull Run Christy
  8. Duck Boot: Sorel Caribou Wool

Should you like the look of a particular boot, you can use the links above to jump straight to it!

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What Are The Most Stylish Winter Boots For Men?

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1. Morjas Alpine Boot [Dress Winter Boot]

Borjas Suede Boots Made In Spain
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A relatively young shoe manufacturer, Morjas has developed a refined collection of traditional dress shoe styles, all of which are crafted by experts in the Almansa region of Spain. Yet, not all of Morjas’ offerings boast classic designs; some of them allow the brand’s unique Swedish heritage to shine through, most noteworthy in this regard is their Alpine boot.

Possessing a design most similar to Chelsea boots but without elastic gussets, the Alpine boots are marked by a zipper at the front of the boot. They also employ a svelte suede upper (available in black or brown), a shearling lining for warmth, Goodyear welt with storm welt for waterproofness, and a lightweight Vibram sole for traction.

While not as rugged as some of the other options on this page, Morjas’ Alpine boots fill an important niche for those who want to maintain a stylish look without sacrificing comfort and warmth during the colder winter months.

2. Ross & Snow Riccardo [Blucher Boot]

Ross & Snow Riccardo Boot
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Reminiscent of classic Red Wings, Ross & Snow’s Riccardo is a cut above any winter boot that we’ve tried. They’re effortlessly stylish but feature sturdy construction and supple rustic-style leather.

The Italian calfskin leather uppers are lined with organically-raised and ethically-sourced shearling wool. As a result, they’re unbelievably warm and it’s sometimes tempting to live the on around the house.

Furthermore, the footbed is removable and you’ll have the choice between a shearling or a cushioned ergonomic insert for additional support. While the regular insert is nice, we can’t help but always wear it with shearling.

As they’re a bit pricey, we invite you to learn more via our review so you can discover why Ross & Snow is the king of the most stylish winter boots.

"Beautifully stylish and unbelievably warm, the Ross & Snow Riccardo is a welcome change to the common winter boot and offers a touch of luxury on cold days."
Bespoke Unit Rating: ★★★★★

3. Johnston & Murphy Shearling [Blucher Boot]

Johnston & Murphy Forrester Shearling Boot
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Our favourite winter boot that is both stylish and practical, these stylish bluchers from Johnston & Murphy feature a genuine shearling lining for extra warmth. Furthermore, the crepe rubber soles ensures good traction whilst a storm welt provides both water resistance and the possibility of recrafting.

How To Wear

These are our number one choice boots for the snow and cold if you want to retain an element of style. Being from the brand’s 1850 Collection, they have an artisanal craft style and are made from burnished Italian calfskin. You can wear them casually or indeed with a business casual suit.

Best Colors

Although they’re only available in brown, we would have likely chosen this colour anyway. The 1850 Collection style has a great rustic vibe, which is further complemented by the natural brown calfskin leather.

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4. Allen Edmonds Dalton Wingtip [Dress Boots]

Allen Edmonds Dalton Wingtip Boots
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Although these aren’t exclusively winter boots, we love Allen Edmonds’ construction that features both a 360° Goodyear welt and Dainite soles. The welt provides water resistance whilst the soles offer fantastic shock absorption and traction. They’re also very stylish and made from premium calfskin leather.

How To Wear

A very formal boot as they go, these are a great choice for the office or special occasions during the winter time. Whilst they’re not lined, the full-grain leather retains heat very well and would be perfect with thick, woollen socks. From business casual all the way to cocktail attire, they’re a great dressy option.

Best Colors

Although plenty of colours are available if you choose the version without Dainite soles, you’d lose out one of their best features. With the soles; they’re only available in either black or brown. We’d go for the black as although wingtips are usually brown, we find that they’re very efficient as dress boots.

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5. Wolverine 1000 Mile Boot [Blucher Boots]

Wolverine Original 1000 Mile Cordovan Boot
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With leather sourced from the Chicago Horween Leather Company as well as a genuine Goodyear welt, the original 1000-Mile boot is a classic. Again, it’s not technically a winter boot but offers great versatility during the colder seasons as well as rugged performance that will see you through it.

How To Wear

More casual than the Allen Edmonds above, these are great boots for casual and business casual wear. However, we’ve been known to wear them with a stylish suit every now and again. If you’re looking for a tough boot, these are a solid choice.

Best Colors

Our favourite is the Cordovan No.8 colour, which has a stunning oxblood hue. However, there’s also rust tan, brown as well as a more formal black.

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6. Irish Setter Wingshooter 808 [Moc-Toe Boot]

Irish Setter Wingshooter 808
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A stunning specimen from Red Wing’s Irish Setter brand, the Wingshooter features a Goodyear leather welt and waterproof UltraDry construction. Whilst they’re not insulated, they retain heat very well and the large moccasin-style toe box leaves plenty of space for thick woollen socks.

How To Wear

These rustic and rugged-looking boots are great for more casual wear. They’d be perfect with worn jeans and a checked shirt. However, they aren’t exclusive to lumberjacks. These are a great practical alternative to the Elk Trackers that we also love for the winter.

Best Colors

Only available in brown leather, this isn’t a surprise given the boot style. We think that it’s the ideal colour and we love the contrast provided by the tan leather welt and black soles.

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7. Danner Bull Run Christy [Work Boots]

Danner Bull Run Christy Winter Boot
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ASTM F2892-11 approved work boots, these proudly American-made soft-toe work boots are durable and impressive. Their handcrafted construction is made from full-grain leather with a comfortable PU footbed and fibreglass shank.

How To Wear

Although these are work boots, we find them so beautiful that we’d wear them casually anyway. The distressed-style and oiled leather is beautiful whilst the cream soles contrast nicely from the tan welt. These are great boots to pair with work-wear inspired styles and offer great comfort during winter.

Best Colors

They’re only available in brown but the colour and leather treatment makes sure that it’s the only colour we’d want them in anyway.

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8. Sorel Caribou [Insulated Duck Boots]

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It wouldn’t be a winter boot list without duck boots. Thanks to the lambswool lining, the Caribou boots by Sorel can withstand temperatures as low as -40°C / -40°F. They’re also very stylish and quite affordable given the style.

How To Wear

Whether you live in the countryside or the city, these are great boots to wear during harsh winters. As duck boots go, they’re among the most stylish with their pebbled leather uppers.

Best Colors

Whilst there’s also a black option available, we favour the brown leather as it has a much more casual and versatile appearance, which will be easier to integrate into your wardrobe rotation.

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Stylishly Wearing Boots For Winter

Man In Duffel Coat & Flat Cap Leaning On Red PhoneboxWhen dressing for the cold, style is not often considered as a priority. Truth be told, it isn’t actually one of the most important factors and the real objective is to stay warm and cosy.

The Danes and Norwegians would be among the first to agree and they know what they’re talking about. Through their long and cold winters, our Scandinavian cousins embrace a cultural phenomenon known as “Hygge”.

Although untranslatable, the word carries strong connotations of comfort, cosiness and wholesome feelings. In short, they reject anything that might be considered an annoyance during winter and simply enjoy the season with their loved ones for what it offers.

As such, style might be one of those very inconveniences that’s left outside to freeze until it thaws come springtime. However, have you seen their sweaters? Anyone who enjoys moody Scandinavian police thrillers have likely noticed the stunning knitwear that they tend to flaunt!

Therefore, it goes to show that style and comfort can go hand-in-hand!

Dressing Appropriately In Winter

Winter outfit including several tweedsSome say that you have to suffer to look stylish. However, don’t feel like you need to wear inappropriate clothing in order to look stylish. That’s the best way to catch a cold.

Instead, it’s important to dress accordingly for the weather but throwing in a few items that add some panache to your wardrobe. Fortunately, we live in a time where knitwear is considered fashionable rather than cripplingly uncool.

Layering up is also a great way to express yourself sartorially with a variety of textures and colours. From tweeds to stylish wool with nuanced details, there’s plenty to choose from.

However, footwear is often a sticking point. Whilst there are a lot of boots and shoes that provide decent year-round performance, many struggled to see you through the winter.

Whether it’s a question of slippery leather soles on the ice or construction that lets in the water, a lot can go wrong. Yet, winter boots are often the garish and heavier cousins of hiking boots. Therefore, you might not be keen on the idea of wearing these when going out.

Minimum Winter Boot Features

Allen Edmonds Dalton Wingtip Brogue Boot Dianite Sole

At the very least, you need a type of footwear that is hardy enough to resist the elements. Fortunately, quality is a significant factor that will affect both the style and the durability of footwear.

Whether it’s construction or the materials used to make them, high-quality craftsmanship is usually able to withstand the winter. For instance, shoe construction plays a pivotal role and Goodyear or Storm welting offers excellent water resistance and durability.

This is why the majority of the dress boots featured on this list are constructed using a Goodyear or Storm welt. Unlike regular winter boots, they’re also recraftable so you’ll be able to change those soles for something with better traction if necessary.

Allen Edmonds Dalton Wingtip Brogue Boots Formal LouvreSole quality is another factor that plays an important role. The winter season means that you’ll encounter more ice and slippery wet surfaces. As a rule, leather soles are out. Not only do they have a tendency to absorb water but they can be very slippery!

Instead, quality rubber soles such as those made by Dainite on Allen Edmonds boots will offer traction, insulation and waterproofing.

On the subject of waterproofing, the construction plays a role but so do the upper materials. Whilst you could go for conventional winter boots that feature nylon or Gore-Tex membranes, quality leather will breathe yet resist water if well-maintained.

Of course, leather won’t provide insulation all by itself. Whilst it acts as a good membrane, it tends to become cold during winter. Therefore, you’ll need something to stay warm.

Some boots do come with lining and there are a few featured here such as the Johnston & Murphy blucher boots. Yet most of the time, it’s good practice to wear some thick socks to create some heat. After that, the leather should offer an excellent layer to let just enough escape for your feet to breathe.

What Next?

Having now explored the most stylish winter boots for men, take a look at some of our related shoe and boot guides:

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