Best Men’s Boots for Fall and Winter

Over the years, men have worn boots for their functionality. The durable design protects your foot from hazards, provides ankle support, and added traction.

But boots are also beloved for their looks and have become a staple in many men’s wardrobes. You can wear boots with almost any outfit and look good.

Although it’s fine to wear boots year-round, Fall and Winter are perfect seasons to sport this versatile footwear.

Our Boot Guide features the best men’s boots for fall and winter and advice on how to wear them.

2020 boot guide

Chukka Boots

chukka boots

Chukka Boots are ankle-high leather boots with suede or leather uppers, leather or rubber soles, and open lacing with two or three pairs of eyelets.

Although no one is sure where the name came from, most people agree that it originated from the game of polo, where a chukka is a period of play.

How to Wear Chukka Boots

Chukka Boots are mainly for casual wear and look best with corduroy, denim, or chinos.

Pair them with henleys, t-shirts, polo shirts, or a patterned button-down to complete your look.

Desert Boots

dessert boot

Desert boots, a type of Chukku boot, trace their origins to Northern Africa and have a long, rugged history.

British soldiers liked the ankle-length shoes because they were durable, comfortable, and well-suited for their desert campaigns during World War II.

Today, Desert Boots are a popular footwear choice for stylish men worldwide.

These boots will bring a refined finish to your outfits.

How to Wear Desert Boots

Desert Boots work with a variety of outfits, however, they look best with casual ensembles.

Wear them with jeans, a T-shirt, and an unstructured jacket, or try them with khakis and a light sweater.

Because of their streamlined silhouette, you can also dress them up with a wool blazer or a modern suit (nix the tie).

Chelsea Dress Boots

chelsea boots

Chelsea Boots are close-fitting, ankle-high boots with an elastic side panel. They often have a loop or tab of fabric on the back of the boot, enabling it to be pulled on.

The boot dates back to the Victorian era when it was worn by both men and women.

Chelsea Boots became popular during the British mod scene in the 1960s and remain a staple item for men’s wardrobes.

How to Wear Chelsea Boots

Because of their classic looks and versatility, Chelsea Boots have become a top choice of fashion stylists.

Many A-list celebrities are rocking these boots while taking a stroll through their neighborhood or walking the Red Carpet.

Chelsea Boots work well with both formal and casual outfits. A simple outfit of fitted chino pants, a crisp, white dress shirt, and a navy blazer will look great with these boots.

You can also go for a mod look with a slim-fit suit with narrow lapels, a thin tie, and a button-down collar shirt.

If you want something more casual, try dark-wash jeans with a chunky shawl-collar sweater.

Zipper Boots 

zipper boots

Zipper boots are a variant of the Chelsea Boot. They are ankle-high and tight-fitting, with a high heel, a pointed toe, and a zipper on the side to help you slide your foot in easier.

Many rock musicians, including the Beatles, have worn versions of these boots.

How to Wear Zipper Boots

The high heel adds a more formal touch to allow you to wear them with edgier outfits such as a bright-color suit and turtleneck

Tall Riding Boots

tall riding boots

Tall riding boots, a type of English riding boots, were created to provide protection and stability during equestrian events and give riders a polished appearance. 

These boots have a small heel, typically about 1″ high, to help prevent a rider’s feet from sliding through stirrup irons. 

They are handcrafted from premium full-grain leather with a high Spanish cut top line and full leather lining.

The contoured ankle design and tighter fit system provide a svelte fit and silhouette.

How to Wear Tall Riding Boots

Although used mainly for equestrian events, riding boots can be worn as a bold fashion statement.

You can wear a traditional riding outfit consisting of breeches, a polo shirt, and/or a jacket. 

Or you can wear them with your everyday outfits to add a touch of pizzazz.

Tall riding boots should fit snugly around your calf and they shouldn’t be too easy to zip up over your calf.

You also shouldn’t be able to move the boots around on your legs once zipped up.

Paddock Boots

best paddock boots

Paddock Boots, sometimes called jodhpur boots, are the choice of footwear for many riders.

Unlike tall boots, they’re as easy to wear as a casual shoe, comfortable while riding and working, easier to care for, and available at a full range of price points. 

These boots are an excellent choice for cold weather outings and activities.

How to Wear Paddock Boots

Paddock Boots are casual footwear that can easily be paired with various types of denim.

Western Boots

ostrich skin cowboy boots

Western boots, aka Cowboy boots, are a style of riding boots. They have a high heel that is traditionally made of stacked leather, rounded to pointed toe, high shaft, and no lacing.

Cowboy boots are traditionally made from cowhide leather but are also made from exotic skins such as snake, ostrich, alligator, lizard, eel, and others.

Cowboy boots come in two styles – Western and Roper. The shaft usually has some sort of decorative stitching or design.

Although cowboy boots were originally designed as footwear for working cowboys in the American West, they have become an acceptable shoe for everyday wear (especially in Texas).

Read our post How to Buy Cowboy Boots for more information on choosing a good fit and style for you.

How to Wear Western Boots

Western Boots look best with jeans. Boot cut styles work best.

If you want a full-on Western look, you can wear jeans, a pearl snap shirt (or another type of shirt with Western accents), a leather belt with a large buckle, and a cowboy hat.

If that’s too much for you, just go with jeans, a T-shirt, and a trucker hat.

You can also get tailored formal garments with Western accents if you want to dress up your boots.

Cap Toe Lace-Up Boots

best boots for fall and winter

While dress boots come in many different styles, the cap toe is classic and elegant. 

The boots feature a smooth leather upper with a burnished toe, breathable, moisture-wicking Suedetec linings, and a fully cushioned, removable Comfortech footbed with Ortholite high rebound foam for long-term wearability.

How to Wear Cap Toe Dress Boots

Cap Toe boots offer endless style possibilities. These boots look great with business casual attire – blazer, oxford shirt, and dress pants.

They also work well with navy or gray classic-fit suits. Or even jeans and a slim-cut V-neck sweater.

Hiking Boots

columbia hiking boots

Hiking boots were created to protect your feet and ankles from rain, muck, puddles, and other hazards while participating in outdoor activities.

Hiking boots are constructed to provide comfort for walking considerable distances over rough terrains such as rocks, grass, gravel, and roots.

How to Wear Hiking Boots

Most people wear hiking boots for their intended purpose – while out on the trails.

The boots go well with hiking gear such as thick socks, pants with extra pockets, and layering items such as thermal underwear, casual shirts, sweaters, and jackets.

Consider selecting material that is wind-resistant, water-repellent, breathable, and lightweight.

Hiking boots can also be worn every day with jeans, chinos, T-shirts, henleys, and plaid shirts.

Timberland Original Yellow Boot

timberland boots

Timberland introduced The Original Yellow Boot in 1973. It was created for hard-working New Englanders, built from 39 components constructed via 80 separate steps, driven by form, function, and craftsmanship.

In the nineties, the humble yellow boot took off as a style icon when hip-hop artists such as Jay-Z, Nas, Treach (Naughty by Nature), MC Lyte, and others gave them street cred.

Now, these iconic boots are seen in the streets and on the runways.

The Timberland Orginal Yellow Boots feature waterproof performance, instantly recognizable work-boot styling, and Wheat Nubuck Leather.

How to Wear Timberland Original Yellow Boots

These boots work well with streetwear style looks. Jeans, graphic t-shirts, hoodies, sweatshirts, denim jackets, and puffer vests all look good with Timberlands.

Check out this Instagram post to see how I styled the Timberland Boots with jeans, a turtleneck, and puffer vest.

Combat Boots

best combat boots

Combat boots were designed to be worn by soldiers during combat or combat training.

Modern combat boots are designed to provide a combination of grip, ankle stability, and foot protection suitable for a rugged environment. They are traditionally made of hardened and sometimes waterproofed leather.

Today, many combat boots incorporate technologies originating in civilian hiking boots, such as Gore-Tex nylon side panels, which improve ventilation and comfort. 

These boots became popular for civilians during the Punk era and saw a resurgence during the Grunge era.

How to Wear Combat Boots

You can put together a 90s styled outfit with a flannel shirt, t-shirt, and jeans. Or you can try a military-inspired look with slim-fit camouflage chinos, a t-shirt, and a bomber jacket.

You can also go full-on punk with black skinny jeans, a t-shirt, and a leather jacket.

 Motorcycle Riding Boots

motorcyle boots

Motorcycle boots are generally made from thick, heavy leather and may include energy-absorbing and load-spreading padding, metal, plastic, and/or composite materials to protect the motorcycle rider’s feet, ankles, and legs in an accident.

Motorcycle boots typically have a long shaft and a low heel so the rider can better control the bike.

The Harley Davidson Booker Motorcycle Riding Boots feature durable leather, an oil-resistant rubber outsole, a locking inside zipper, and reliable Goodyear welt construction. 

How to Wear Motorcycle Boots

A black T-shirt and jeans are the perfect accompaniment to these boots. Add a leather motorcycle jacket or racing jacket and you have the perfect outlaw look.

What is Your Favorite Type of Boot?

We hope this Fall and Winter Boot Guide has been helpful. We’d love to hear from you. Do you own any of the boots listed in our boot guide? What is your favorite type of boot?

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