Best Men’s Winter Dress Boots

With the darker weather and colder temperatures moving in, your low-cut dress shoes that let the chill in just won’t cut it for the winter. Instead, you’ll need a pair of durable winter boots, and perhaps more than only one pair.

Winter boots have gained popularity over the past few years, with more men choosing to wear these trendy shoes to work, as well as for everyday wear. If you are looking for a good, sturdy pair of boots that look fashionable yet will still get you through the winter, then you’ve come to the right place.

In this article, we share five different pairs of the best men’s winter dress boots to give you some inspiration and hopefully allow you to find a suitable pair for yourself. We have done our research and only included boots that are capable of meeting all your winter needs.

What to Look for in Winter Dress Boots?

Practicality

You’ll want to purchase boots that can be worn to work but also to walk around the city. Those boots with too thick a sole might be less suited to workwear, and more outdoor wear, so it’s important to find a pair that can be practical for any location or situation in winter.

Strong Design

As the winter brings strong winds and lots of rain or snow, you will, therefore, require a well-designed boot that isn’t likely to fall apart at the slightest bit of weathering. The stronger the material, the better the durability, and this is what you’ll want in a winter boot.

Comfort and Breathability

Comfort is crucial in a winter boot as you’ll most likely be wearing them often. Breathability is another factor to look for as most boots will be tight fitting, so if you are wearing them regularly, try to find ones which offer the right amount so your feet won’t sweat.

Comparison Chart

La Milano Men's Leather Cap Toe Lace Up Winter Casual Dress Boot Classic Comfortable Dress Shoes for Men
Florsheim Men's Medfield Plain Toe Zip Boot Fashion, Brown, 10 Medium
Blondo Men's Mickey Waterproof Winter Boot, Black Leather, 11 M US
GM GOLAIMAN Men's Oxford Dress Wingtip Brogue Boots - Black Brown Lace-Up Zip Boots Ankle Dress Boots Work Combat Hunter, Brown 7 (M) US
Cassa Leeni Men's Chelsea Boot Winter Boot Warm Fur Lined Leather Dress Casual Ankle Boot
La Milano Men's Leather Cap Toe Lace Up Winter Casual Dress Boot Classic Comfortable Dress Shoes for Men
Florsheim Men's Medfield Plain Toe Zip Boot Fashion, Brown, 10 Medium
Blondo Men's Mickey Waterproof Winter Boot, Black Leather, 11 M US
GM GOLAIMAN Men's Oxford Dress Wingtip Brogue Boots - Black Brown Lace-Up Zip Boots Ankle Dress Boots Work Combat Hunter, Brown 7 (M) US
Cassa Leeni Men's Chelsea Boot Winter Boot Warm Fur Lined Leather Dress Casual Ankle Boot
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La Milano Men's Leather Cap Toe Lace Up Winter Casual Dress Boot Classic Comfortable Dress Shoes for Men
La Milano Men's Leather Cap Toe Lace Up Winter Casual Dress Boot Classic Comfortable Dress Shoes for Men
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Florsheim Men's Medfield Plain Toe Zip Boot Fashion, Brown, 10 Medium
Florsheim Men's Medfield Plain Toe Zip Boot Fashion, Brown, 10 Medium
Blondo Men's Mickey Waterproof Winter Boot, Black Leather, 11 M US
Blondo Men's Mickey Waterproof Winter Boot, Black Leather, 11 M US
GM GOLAIMAN Men's Oxford Dress Wingtip Brogue Boots - Black Brown Lace-Up Zip Boots Ankle Dress Boots Work Combat Hunter, Brown 7 (M) US
GM GOLAIMAN Men's Oxford Dress Wingtip Brogue Boots - Black Brown Lace-Up Zip Boots Ankle Dress Boots Work Combat Hunter, Brown 7 (M) US
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Cassa Leeni Men's Chelsea Boot Winter Boot Warm Fur Lined Leather Dress Casual Ankle Boot
Cassa Leeni Men's Chelsea Boot Winter Boot Warm Fur Lined Leather Dress Casual Ankle Boot
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Best Men’s Winter Dress Boots Reviews

La Milano Mens Lace-up Dress Boots

La Milano Men's Leather Cap Toe Lace Up Winter Casual Dress Boot Classic Comfortable Dress Shoes for Men

The first pair of winter boots featured on our list is the Mens Lace-up Dress Boots by La Milano. These offer a very sleek look and are great for cold weather.

Pros

  • Full leather upper
  • Lace-up style
  • Memory foam insoles
  • Cap toe design
  • Durable and flexible
  • Versatile

Cons

These boots make a bit of noise when walking

Summary

La Milano has been making innovative footwear for men since 2003. They incorporate style, comfort, and durability into every shoe they produce. They strive to create top-quality footwear at a reasonable price.

Comfort technology

La Milano’s dress boots have been designed with a soft memory foam insole. This gives the wearer incredible all-day comfort, making them the perfect shoe for long-period wear. The added faux fur lining also allows for extra support around the feet and ensures they will be kept warm in cold temperatures.

Stable soles

The soles are a vital factor you will want to consider when purchasing winter boots. La Milano has thought ahead when making their boots, and indeed, provide durability. Thanks to the robust and durable rubber outsoles, these boots will last a long time. The outsoles also provide non-skid stability, giving the wearer more stability and balance when walking.

Stylish design

These dress boots feature a trendy design and come in four different color varieties. This includes whiskey, black, brown, and black with a dark sole. They also feature a cap toe design with stitching, which gives them a stylish appearance.

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Florsheim Men’s Medfield Plain Toe Boot

Florsheim Men's Medfield Plain Toe Zip Boot Fashion, Brown, 10 Medium

The second pair of winter dress boots featured on our list is the Medfield Plain Toe boots by Florsheim. These are a classic style of boot which have some pretty nice features.

Pros

  • Classic style
  • Rubber sole
  • Leather design
  • Breathable lining
  • Fully cushioned insoles
  • Stability heel cup

Cons

Zipper tends to be defective

Summary

Florsheim is a shoe company which started in 1892; therefore, you can expect to receive good quality when purchasing their shoes. With so many years of craftsmanship behind them, their boots offer genuine leather designs and varying styles.

Breathable boot

Breathability is an essential factor in a winter boot, as you will most likely be wearing them for the majority of the time throughout winter. Therefore, you will need a boot that won’t get too hot indoors and make your feet sweat.

These boots feature lining that is moisture wicking Suedetec. This removes any bacteria build-up and therefore stops any sweat from occurring.

Comfortable

The Florsheim boots also boast a good amount of comfort thanks to their fully cushioned insoles. These insoles are carefully made using Ortholite high-rebound foam, which is shock absorbing and doesn’t require as much breaking in as standard boots. These are removable and also feature a stability heel cup to provide the wearer with extra stability in their step.

Classic style

Florsheim offers traditional, vintage-looking boots which give the wearer a classic appearance. These boots are crafted in real leather and include a burnished finish and a variety of patterns. The uppers are also made in genuine leather, and the soles are durable and slip-resistant.

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Blondo Mens Mickey Waterproof Winter Boot

Blondo Men's Mickey Waterproof Winter Boot, Black Leather, 11 M US

The third pair of men’s winter dress boots on our list is the Mickey Waterproof Winter Boots by Blondo. These offer a warm and classic appearance and are great for rainy, wet conditions.

Pros

  • 100% leather
  • Strong, rubber sole
  • Waterproof design
  • Sealed seams
  • Durable
  • Versatile
  • Cozy fleece lining

Cons

These boots look huge, and reports of the zipper breaking not too long into ownership

Summary

Established in the mid-1980’s Blondo has been making stylish waterproof leather boots ever since. They focus on the durability and function of boots and keep them trendy and fashionable at the same time.

Insulated design

When it comes to winter, the warmer the boot, the better. That’s why you will love these boots by Blondo as they feature 100% natural wool lining in their interior. This makes for a very comfortable, cozy fit which will keep the warmth inside and keep you protected from the cold.

Waterproof

The best feature these Blondo winter boots boast is their waterproof design. With all the lousy weather during winter, a waterproof boot is probably the best option to go for. The waterproof leather in these boots will keep you dry at all times, and at the same time, they also repel salt so they should last a long while.

Durable sole

A sturdy sole is an important factor in winter boots, and the Mickey waterproof winter boots do provide, with their strong, durable soles. These are full-traction rubber and will help the wearer to overcome any obstacle in their path. They also feature anti-slip properties, meaning they are perfect for wearing in both icy and snowy conditions.

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GM Golaiman Mens Oxford Winter Boots

GM GOLAIMAN Men's Oxford Dress Wingtip Brogue Boots - Black Brown Lace-Up Zip Boots Ankle Dress Boots Work Combat Hunter, Brown 7 (M) US

The fourth pair of winter boots on our list is the Mens Oxford Winter Boots by GM Golaiman. These are a lace-up style of boots which are perfect for work and casual everyday wear.

Pros

  • Synthetic leather
  • Brogue lace-up style
  • Memory foam insoles
  • Non-skid outsoles
  • Side zippers
  • Versatile

Cons

Complaints that the soles came apart from the boot within a few weeks

Summary

GM Golaiman offers its Knight collection, which provides a stylish, elegant design which is perfect for almost any occasion. They are perfect for casual business occasions to family travels and city visits.

Premium leather style

The Oxford-style winter boots by GM Golaiman were created using premium leather. This provides a very soft texture and delicate feel, allowing the wearer ultimate comfort. This leather offers just the right amount of resistance for day to day wear and helps the boots to last a long time.

Stylish and elegant design

If you want a pair of boots that offer a good amount of style, these boots are for you. These winter boots feature a classic-style brogue with a wingtip to provide a more superior look. To finish the look, a rich gloss has been applied, which is also dirt resistant and allows for easy maintenance.

Comfort guaranteed

Thanks to their memory foam insole, these boots are perfect for everyday wear. The insole features arch support which aims to improve posture, and at the same time provide multi-protection to keep feet in the best shape possible. They also feature a non-skid TPR sole, which helps reduce any foot fatigue when walking for long periods.

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Cassa Leeni Mens Chelsea Boot

Cassa Leeni Men's Chelsea Boot Winter Boot Warm Fur Lined Leather Dress Casual Ankle Boot

The fifth and final pair of winter dress boots featured on our list is the Mens Chelsea Boot by Cassa Leeni. The Chelsea boot is a popular style of men’s boot and one which can even be worn in winter thanks to their durable design.

Pros

  • 100% genuine leather
  • Zero harmful chemicals
  • Durable rubber outsoles
  • Anti-skid properties
  • Soft, thick fur lining
  • Flexible side zipper
  • Cozy

Cons

The sizes run a bit large

Summary

Are you on the lookout for a stylish Chelsea style boot which will keep you warm in winter? The Mens Chelsea Boots by Cassa Leeni are the perfect match for you. Not only do these boots provide true Italian craftsmanship, but also durability to last you throughout the entire winter season.

Durable outsoles

You will need a pair of boots with a pretty sturdy outsole to survive in severe weather conditions. These Chelsea boots have been designed with durable rubber soles which are thick enough to protect your feet from any injury. Their anti-skid properties also help keep the wearer from slipping on ice and therefore offer more stability.

Keep you warm

The best feature of these winter boots? Their interior. Usually, it’s not common to find a pair of Chelsea boots with insulated, fur lining. Cassa Leeni’s boots, however, offer just that with their incredibly soft and thick fur lining inside the boots, which better protect your feet from frost, ice and snow. This increases the overall coziness and comfort levels altogether so that it’s entirely possible you might not want to take these off.

Perfect for any occasion

When purchasing a winter boot, you want to make sure that it can be worn on many different occasions. These casual leather ankle boots are perfect for everyday wear to work, business meetings, formal dress, weddings, casual and even parties. Therefore, you don’t need to worry about these boots only being suitable for one occasion, as they can fit many.

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Which are the Best Men’s Winter Dress Boots?

So which are the best men’s winter dress boots currently available? We think that all the above featured on our list are guaranteed to keep your feet warm and will last through the winter.

If you are shopping on a budget, however, you might be more keen to find the most reasonably priced option, which on this list are the Mens Oxford Lace-up Boots by GM Golaiman. These offer a significant amount of durability for a great price. Or if you prefer the look of La Milano’s Oxford Winter Boots, these are the second least expensive option.

At the opposite end of the scale, the most expensive are the men’s Mickey Waterproof Winter Boot by Blondo. The fact that these boots are entirely waterproof makes them a viable option for keeping your feet warm and dry during winter weather.

Winter dress boots continue to be a popular style of boot to wear, and they are often great for matching with many outfits and for wearing on a variety of occasions.

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