Columbia's Sunvent Chukka

Trading suede for distressed canvas upper with an extra-spongy rubber sole, Columbia Sportswear's Sunvent straddles the ruggedness of a boot with the comfort of a sneaker. With excellent traction and water-draining ports, it's a safe pick for hiking and boating, but really shines when you're playing tourist. Weighing in a under 9 ounces, these are the perfect shoes to toss in your suitcase for trips that will have you on your feet. [Sunvent Boot, $100, columbia.com]