Best Boots for Fall

Here’s the scenario: You’re assembled the perfect outfit. You’ve got a impeccably tailored suit, a tie that’s sleek and sophisticated, and maybe one of these 6 Top Style Accessories for Men. And then you finish the look with … a pair of clunky, square-toed motorcycle boots.Well, maybe you can get away with it. I mean, women never look at a guy’s shoes, right? Oh wait.

Don’t let the last piece of your outfit be an afterthought. Be deliberate in your footwear choices this season. Pick sleek, waterproof boots for dreary weather and wingtips for business meetings.

And if you choose your shoes carefully, they can be a solid investment you’ll still be wearing through the spring.

THE MIXED MEDIA

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10/16 IMAGE COURTESY OF TO BOOT NEW YORK

Two-toned military-inspired boots are a surefire way to keep your twill trouser and button-down combo on its A-game.

$220, Buy It Here

THE SUEDE BOOT

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9/16 IMAGE COURTESY OF J. CREW

These simple suede boots are your next go-to casual shoe. They’re even specially crafted for the long haul, so you can easily resole the bottoms once you wear them out.

$148, Buy It Here

THE WEST HAVEN BOOT

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8/16 IMAGE COURTESY OF TIMBERLAND

Not your dad’s work boots. These everyday Timberlands are made with anti-fatigue technology, which boosts foot support and shock absorption so you can stay on your feet all day.

$100, Buy It Here

THE DESERT BOOT

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7/16 IMAGE COURTESY OF CLARKS

Every man needs a classic desert boot—the crepe sole adds spring to your step, and the equally easy shape complements everything from cords to chinos.

$130, Buy It Here

THE CHELSEA BOOT

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6/16 IMAGE COURTESY OF VINCE

Bring the boots on your next business trip. They’re easy to slip on, stylish, and comfortable enough to trek through a new city.

Starting at $245, Buy It Here

THE ENGINEER’S BOOT

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5/16 IMAGE COURTESY OF L.L. BEAN

The tough oiled leather exterior and cork and rubber outsole on these turn jeans and a T-shirt into a rugged, off-duty look

$239, Buy It Here

THE RAIN BOOT

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4/16 IMAGE COURTESY OF TRENTORN

Storms don’t have to bring you down. Keep your feet warm and comfortable with these micro fleece and rubber boots.

Starting at $82, Buy It Here

THE EISNER BOOT

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3/16 IMAGE COURTESY OF ECCO

This boot is your go-to game day shoe. Whether you’re cheering in the stadium or at the local bar, these casual boots are best paired with wings and beer. Now that’s a win.

$118, Buy It Here

THE DUCK BOOT

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2/16 IMAGE COURTESY OF BARBOUR

Duck boots are a game-changer. They’re waterproof and sturdy, so these boots are made to trudge through slush and snow.

$84, Buy It Here