2026’s Top 5 Men’s Winter Shoe Styles and Buying Guide

Are you ready to embrace the cold season with both style and comfort? Securing the right overcoat is essential, but equally important is selecting the right winter footwear to keep your feet warm and dry. Fortunately, you don’t have to spend months confined to bulky leather boots. For those who prefer a more breathable option, there are numerous low-top styles that still offer warmth and protection from the elements.

While winter shoes might not get as much attention as their boot counterparts, a variety of appealing styles are available. These include sneakers and shoes that are insulated, waterproof, or come with specific features designed for cold weather. With choices that span from casual to smart, there’s no reason to compromise on comfort regardless of your destination. Below is a selection of essential winter footwear styles for men.

What Makes A Good Winter Shoe?

Waterproof

Converse

While winter shoes don’t have to be waterproof, many people prefer them to be, especially in regions with frequent rain. Keep in mind that waterproof materials can sometimes lead to overheating and a lack of breathability. If you live in a particularly wet area, look for shoes with a Gore-Tex liner—the gold standard for waterproofing that allows moisture to escape while keeping external water out.

Warm

Hunter

If your winters are particularly chilly, consider shoes that feature some insulation. This could be as simple as selecting a padded sneaker instead of an unlined leather model or finding footwear designed with built-in synthetic or pile insulation.

Grippy

Velasca

During winter, wet leaves, ice, and slippery sidewalks can be hazards. Some materials—like leather, crepe rubber, and flat soles—are not ideal in these conditions. A good winter shoe should offer reliable grip, either through special rubber compounds or pronounced lugs on the sole for enhanced traction.

Durable

Kleman

Your winter footwear must withstand whatever the season brings. Look for well-constructed shoes made from materials that can endure harsh weather. Avoid delicate materials like suede, mesh, and canvas; instead, opt for sturdy choices like smooth leather, rubber, and durable synthetics.

5 Key Winter Shoe Styles For Men

Commando Sole Derby

Velasca

The Derby shoe remains one of menswear’s enduring classics. Its straightforward design has been creatively reinterpreted by countless designers, ensuring it remains relevant today. However, traditional Derby shoes can struggle on slippery surfaces due to their flat leather soles.

If you wish to maintain the elegance of this classic footwear while ensuring stability, opt for a Derby model with a lugged commando sole. This innovation enhances grip and traction, keeping you steady and stylish throughout the winter months.

House Shoes

Velasca

As energy costs rise, staying warm at home has never been more critical. A comfortable pair of house shoes is an excellent starting point. These hybrid slipper-shoes range from Birkenstock Bostons to The North Face Tent Mules. This category offers a wide variety of styles, gained immense popularity during the pandemic. Essentially, they provide warm, comfortable footwear meant for indoors but durable enough for quick trips outside.

Trail Runners

Salomon

It’s remarkable how much trail-running shoes have evolved in the past decade. Today, they are a prominent feature in the realm of men’s fashion. The trend toward off-road runners likely stemmed from the rise of bulky silhouettes in footwear around 2017. It’s now common to see brands like Salomon and Hoka One One making waves in urban settings.

Regardless of personal style, these functional shoes offer substantial comfort, superb grip, and often feature Gore-Tex liners, making them ideal for winter wear.

Rubber Shoes

Swims

This category includes stylish rubber shoes that serve as low-top alternatives to traditional Wellingtons. While they may not offer the highest versatility in style, their waterproof capabilities are second to none. They’re perfect for quick outdoor ventures during dreary weather, and galoshes can even be worn over regular shoes to keep them dry.

Waterproof Sneakers

Adidas

There’s no need to retire your sneakers for winter; with the right waterproof options, you can easily adapt them to the season. The recent trend in functional footwear has led to a proliferation of stylish Gore-Tex shoes available. Brands like Salomon, Arc’teryx, Nike, and New Balance are all worth exploring for their impressive waterproof designs, including Converse’s own Gore-Tex Chuck Taylor model.