5 Best Men’s Winter Dress Boots

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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 dress boots for men, 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 dress shoe boots to work, as well as for everyday wear. If you're 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 review 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've done our research and only included boots that are capable of meeting all your winter needs.

What to Look for in Dress Boots for Winter?


You'll want to purchase men's shoe 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 to 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'll therefore require a well-designed boot that isn’t likely to fall apart at the slightest bit of bad weather. 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 dress 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're wearing them regularly, try to find ones which offer the right amount of breathability so your feet won't sweat.

Comparison Chart

La Milano Men's Leather Cap Toe Lace Up Dress Boot 

Florsheim Men's Medfield Plain Toe Zip Boot

Blondo Men's Mickey Waterproof Winter Boot

GM GOLAIMAN Men's Oxford Dress Wingtip Brogue Boots

Cassa Leeni Men's Chelsea Boot

5 Best Picks

1. La Milano Mens Lace Up Dress Boots

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.


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'll be kept warm in cold temperatures.

Stable boot soles

The soles are a vital factor you'll 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 good non-skid stability, giving the wearer more confidence 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.


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


  • These boots make a bit of noise when walking

2. Florsheim Medfield Men’s Plain Toe Boot

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 men's boot which have some pretty nice features.


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'll 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 or odor from occurring.

Comfortable men's dress boots

The Florsheim boots also boast the right 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 insoles are removable and also feature a stability heel cup to provide the wearer with extra support in their step.

Classic men's boot 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.


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


  • Zipper tends to be defective

3. Blondo Mickey Men's Waterproof Winter Boot

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.


Established in the mid-1980’s Blondo has been making stylish waterproof leather boots ever since. They focus on their durability and function 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'll 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 Winter Dress Boots

The best feature these Blondo winter boots boast is their waterproof design. With all the lousy weather during winter, a waterproof boot is probably a good 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 boot sole

A sturdy sole is an important factor in winter boots, and the Mickey waterproof winter boots provide this 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're perfect for wearing in both icy and snowy conditions.


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


  • Some report the zipper breaking not too long into ownership

4. GM Golaiman Men's Oxford Winter Boots

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


GM Golaiman offers its Knight collection, which provides a stylish, elegant design that's perfect for almost any occasion. They're ideal 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 smart men's dress boots, then these 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 finish has been applied, which is also dirt resistant and allows for easy boot care 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 foot fatigue when walking for long periods.


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


  • Some suggested the soles could be more durable

5. Cassa Leeni Men's Chelsea Boot

The fifth and final pair of winter dress boots featured on our list is the Men's 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.


Are you on the lookout for a stylish Chelsea style boot which will keep you warm in winter? These Mens Chelsea Boots by Cassa Leeni may be perfect choice 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'll need a pair of boots with a pretty sturdy outsole to survive in severe weather conditions. These Chelsea boots for men have been designed with durable rubber soles which are thick enough to protect your feet from any injury. Their anti-skid properties also helps to keep the wearer from slipping on ice, providing added stability.

Boots that keep your feet 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 men'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 them 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.


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


  • The sizes run a bit large

Which Winter Dress Boots to Choose?

So which are the best men’s winter dress boots currently available? We believe all of the shoe boots reviewed in this article will keep your feet warm and will last through the winter.

If you're shopping on a budget, however, you might be keener to find the most reasonably priced option, which on this list is 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 wet winter weather.

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

Last Updated on December 19, 2021 by admin_comfortabledressshoes