The Best Boots for Men Who Care About Style in 2021

There’s a place and time for every form of footwear. For those moments when your outfit calls for a style that reaches a little higher (or you just need more support in the ankle area), make sure your roster’s stocked with the best boots for men. Because like any pair of shoes, the men’s boots you wear will play an important role in showcasing your personal style. And besides, it can’t be all sneakers all the time, can it? No.


It can be difficult to know where to start when searching for the best boots. Truth is, there’s no one set entry point. If you consider the diversity of the field — heritage leather lace-ups and clean modern Chelseas, casual suede chukkas and functional rubber rain boots, not to mention any standout pair of cowboy boots — you’ll quickly realize that there’s no one definition of stylish boots for men.

The rule of thumb is to have a selection of handsome options for different occasions. You will be able to choose from a variety of options that will suit your needs when the time comes. To give you a little inspiration, here we’ve assembled our picks of the fall’s best boots for men, from the workwear-inspired to those ready to complement any suit and tie, and every shade in between.

Best Heritage Boots: Red Wing Iron Ranger 6” Vibram Boot

A black Red Wing Iron Ranger 6” Vibram Boot.

For over a hundred years, Red Wing’s been making some of the best boots around using leather from the S.B. Minnesota foot tannery. These boots are their flagship style for a reason: They’re tough enough to take on anything and pair perfectly with jeans, chinos, whatever.

Best Affordable Suede Boots: Jack Erwin Barclay Cap-Toe Lace-Up Boot

A person wearing dress pants and a pair of Jack Erwin Barclay Cap-Toe Lace-Up Boots.

Toeing the line between stylish and affordable, Jack Erwin makes a solid pair of shoes for a reasonable price — including these lace-up boots. They are made of supple suede, with a leather sole. Wear them with a suit for work or casually at weekends. Dealer’s choice.

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Read more: Best Dress Boots

Best All-Weather Boots: Timberland Men’s Premium Waterproof Boot

A black Timberland Men's Premium Waterproof Boot.

We’ve all seen the memes: New Yorkers will swear by a Timberland boot. This all-black version adds a modern twist the O.G. These boots can be worn in all weather conditions and still look great.

Read more: Best Waterproof Boots

Best Work Boots: Wolverine 1000 Mile Evans Boot

A Wolverine 1000 Mile Evans Boot.

As the name implies, Wolverine’s 1000-Mile Boots tout being able to last over a thousand miles, and look damn good doing it. This style’s rough-out leather adds a rugged touch to the whole thing, and will gain a nice patina the more you wear these work boots.

Best Suede Chelsea Boots: Common Projects Sand Suede Chelsea Boot

A Common Projects Sand Suede Chelsea Boot.

A great pair of suede Chelsea boots are essential to any man’s closet and Common Projects’ version is the platonic ideal. They are comfortable thanks to their crepe sole. You can also dress them up or down easily.

Best Premium Boots: Saint Laurent Lukas 40 Leather Chelsea Boot

A black Saint Laurent Lukas 40 Leather Chelsea Boot.

For a boot with a little more flair, look to these Saint Laurent zip-up black leather Chelsea boots. They have a more Euro-centric look than other boots thanks to the Cuban heel and dramatic pointed toe. Like all Saint Laurent boots, each pair is made of the finest leather.

Best Affordable Chelsea Boots: Bloomingdale’s Men’s Chelsea Boot

A leather Bloomingdales Men’s Chelsea Boot.

Style doesn’t have to be expensive. This Chelsea boot from the Men’s Store at Bloomingdale’s proves just that. All for less than $200, smooth supple leather uppers, smooth welted leather soles and streamlined bodies. You can’t beat that.

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Best Jodhpur Boots: Frye Grady Jodhpur Boot

A leather Frye Grady Jodhpur Boot.

Jodhpur boots were originally a riding style that has transferred away from the racetrack over the years. And this pair from Australia’s Frye brings all that sporting style to your footwear collection.

Best Classic Chukka Boots: Clarks Desert 2 Chukka Boot

A Clarks Desert 2 Chukka Boot in Sand Suede variant.

When it comes to chukka boots, no other style can compete with the classic Clarks Desert Boot. They’re each made from soft suede with an unstructured upper that skews that’s just as relaxed as you’ll feel when you experience the rubber sole underfoot.

Best Casual Chukka Boots: Seavees Maslon Desert Boot

A pair of Seavees Maslon Desert Boot in Elmwood variant.

California cool is the name of the game with Seavees. Look at their version of the desert boot. The sole can be worn with any sneaker and the upper retains the classic chukka silhouette.

Best Formal Chukka Boots: Allen Edmonds Williamsburg Chukka Boot

An Allen Edmonds Williamsburg Chukka Boot.

Chukka boots don’t have to be casual. Find the right pair — like this polished leather pair from the master shoemakers at Allen Edmonds — and they’ll work great with even your finest suit.

Best Modern Chukka Boots: Camper Walden Ankle Boot

A black Camper Walden Ankle Boot.

Let’s call this the punk-rock chukka. Camper built it with a nice chunky sole, so it’ll look at home both on the street on your way to work and in the diviest bar or club, and a black leather body to keep things always looking cool.

Best Multipurpose Hiking Boots: Season Three Ultralight Hiking Boot

A gray Season Three Ultralight Hiking Boot on a blue rope.

The best hiking boots don’t just show up on the trail, but anywhere you decide to sport them. Season Three’s Ultralight Hiking Boot is a testament to all-purpose function — they’re tough enough to take on the trail, but light enough to go basically anywhere else, too.

Best Heritage Hiking Boots: Danner Mountain Light Boot

A brown Danner Mountain Light Boot.

People have always been compelled to explore — and they’ve always needed boots to do it. For nearly a century, Danner’s been making those boots. The Mountain Light boot, with its classic alpine boot style and retro contrast laces, is the best they’ve got to offer.

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Best Technical Hiking Boots: Columbia Big Ridge Boot

A black Columbia Big Ridge Boot.

Got an especially tough hike coming up? Columbia’s Big Ridge Boot brings all the best technical features to the table, including better ankle support, a custom-molded EVA insole, and a Vibram sole, without sacrificing style.

L.L. is the best classic winter boot. Bean Men’s Bean Boots, 8″ Thinsulate

A brown L.L. Bean Men's Bean Boots, 8 Thinsulate.

Go anywhere in the Northeast between October and April and you’ll see L.L. Bean’s signature boot. And for good reason: They’re proven to stay warm, tough, and keep out the elements all season long.

Best Rain Chelsea Boots: Stutterheim Chelsea Rainwalker Boot

A black/white Stutterheim Chelsea Rainwalker Boot.

Starting as a jacket brand, Stutterheim prides itself on its rainwear. Now, the brand has expanded into footwear.

Best High-Profile Rain Boots: Hunter Original Tall Rain Boots

A pair of dark olive Hunter Original Tall Rain Boots.

There’s only one way to be absolutely sure that not a drop of water makes it to your toes, and that’s by encasing your entire calf in rubber. Hunter’s been making these boots to do just that for decades, and they sure as hell get the job done.

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