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
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
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
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
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
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
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
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