The 5 Best Boots For Men

Let’s face facts: when the weather gets cold, your little piggies become dangerously exposed.

Mesh sneakers let in freezing air, canvas shoes become sponges in snow, and anything low top spells doom for your ankles.

To top it all off: when your body cools, your nervous system draws blood away from extremities to keep your heart and lungs at optimal warmth.

Literally and figuratively, things aren’t looking too hot for your feet.

Thankfully, this isn’t humanity’s first winter. Since prehistoric times, a simple footwear formula has fought off ice and wind:

wrap foot in leather, make high-top, repeat.

While we’ve added all sorts of stylish and functional variation over the years, both the formula and its output have remained about the same.

Take it from the cavemen – if you’re looking for rugged, rakish, winter-proof footwear, look no further than boots.



Cataloging boot styles is like trying to make a list of everything: noble, yet ultimately fruitless.
While a Master’s of Boot History would look nice on a wall in our office, no one should have to read a dissertation on footwear to nail their style.

With your busy schedule in mind, we’ve distilled the universe of boots into the 5 essential styles making an impact on fashion today. Even better: the list below is ordered from most functional to purely fashionable, outlining exactly how each style will fit your needs.

From the street to the runway, city to the country, these boots will keep you warm – and look great doing it.

Work Boot


What you need when there’s a job to be done. Work boots are chunky, weatherproof, and built for function. The style is there, too – it’s just not the focus.

Instead, work boots emphasize pure utility through features like treaded outsoles, waterproof liners, and insulated uppers.

Whether snow or mud stands in the way, a modern work boot will keep what’s outside… well, outside.

But that’s not to say they can’t look good doing it. Thanks to societal trends towards casual wear and urbanization, work boots from brands like Timberland and Rothco have become fashion pieces in their own right.

Timberland’s “Wheat 6” Boot” has even achieved cultural icon status all its own, thanks to co-signs from musicians, fashion designers, and celebrities of all spades. Most importantly of all, it’s still trusted by the millions who rely on it.

Are work boots as fashionable as their suede-and-crepe cousins? That’s for you to judge. One thing’s for certain: in 2 feet of snow, the best look is the one that’s warm and dry.


Heritage Boot


What you think of when you think of “boots.” Heritage-style boots are made to look like the utility boots of old, with varying degrees of modernity depending on the model.

Typical features include leather soles, waxed laces, and “Goodyear” welting (a special method of attaching the boot’s upper to its sole).

Think of heritage boots as the perfect compromise between fashion and function. While they may lack the durability of modern work boots, heritage boots are rugged enough for snow-choked sidewalks and arguably look better with heavy use.

Some shoemakers (Viberg, Red Wing Heritage, Wolverine) even still make boots by hand, insisting on the highest-quality craftsmanship for each and every pair.

By reaching to the past, heritage boots have built a presence in our present.


Dress Boot


What you wear on Casual Friday, but all the other days, too.

Dress boots have much in common with heritage boots, yet are typically made in fashion-friendly materials and designed to mimic dress shoes from the ankle down. These formal-focused boots often feature exotic leathers, thin laces, and decorative broquing.

Dress boots are the footwear equivalent of “loosening your tie” – the high-top marks them as decidedly informal, yet with the right pants, most can pass for officewear in a pinch. In the heyday of the menswear trend, dress boots dominated.

From the streets of Milan to the New York subway, the world’s most stylish guys flocked to brands like Alden, Saint Crispin’s, and Allen Edmonds for their devotion to quality. While #menswear has come and gone, those same shoemakers continue to turn out gorgeous dress boots worthy of envy.

Fair warning: dress boots don’t come cheap. However, for their versatility alone, good dress boots are well worth the investment.


Chelsea Boot


What you wear to the office, the Kanye show, and everything in between.

Chelsea boots are round-toe boots fitted with an elastic webbing instead of lacing, making them both easy to put on and distinctively fashionable. While Chelseas can come in either suede or smooth leather, the typical pair includes a leather sole, rounded toebox, and minimal stitching.

Although sacrificing the grip of laces may mean decreased usability, any worries about utility fade away the second you slip into a pair. Chelsea boots are built to provide a different kind of utility: the kind that quietly improves your everyday life.

For one, they’re effortlessly stylish. Chelseas pair with everything from ripped denim to Italian suiting, fitting both streetwear and formal styles with ease.

For two, they’re easy to wear. You never know how much you hate tying your shoes until you never have to do it.

Finally, they’re available at every price point. From ASOS to Common Projects to Saint Laurent, there’s a pair of Chelsea boots out there that will fit your taste and your budget.

If you live below the snowline, there’s no reason not to own a pair of Chelsea boots. If you live above it, get two pairs just to be safe. Your wardrobe will thank you.


Avant Garde Boot


Avant-garde boots are any boots that riff on typical styles to create something entirely new.

There are few good ways to describe the typical avant-garde boot, since the style as a whole is defined by being anything but typical. Instead, go with your gut: if it features exaggerated proportions, unexpected materials, or a remixed entry system (read: zippers on zippers), it likely fits this category.

To be blunt, avant-garde boots are hard to wear. Unless you have an entire wardrobe built to support them, boots from designers like Rick Owens, Guidi, and A 1923 will look out of place rather than really frickin’ cool. Which is a shame, since with the right context (read: black on black) and outfit (read: layers on layers), avant-garde boots look really frickin’ cool.

It should be assumed that boots you need to build an entire outfit around aren’t really designed for function, but for clarity’s sake: don’t wear avant-garde boots unless it’s 60 and sunny.

For their price tag, unfamiliar styling, and lack of utility, most guys found avant garde boots completely inaccessible. However, if you have the confidence (and the capital) to pull them off, by all means, go for it. The rest of the world will catch up.


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