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

THE WINGTIP

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1/16 IMAGE COURTESY OF BARNEY’S NEW YORK

Complete any formal look with these killer wingtips. They’re just right for pairing with modern suits or tailored bottoms.

$349, Buy It Here