The Bahama chukka raises the original Sperry Top-Sider canvas boat shoe to a higher profile. Featuring a touchably soft and smooth canvas upper, contrasting stitching accents, and a moc-style toe, this sporty, sneaker-style boot is a summer style you'll want to live in year-round. Full of relaxed touches like the laced sides and a four-eye, lace-up front with metal logo eyelets and...
Unleash your inner rock star with this stylish boot. The rich leather upper features buckled straps at the ankle and top of the shaft, one of which is studded to match studs that trail up the back of the boot. A side zipper and rubber sole make this a boot that will be so comfortable that you'll reach for it again and again.
Urban appeal meets rustic perfection in this men's Niles boot by the trendsetters at Guess. Crafted of slightly distressed leather with heavy stitching accents and silver hardware, the lace-front boot wears like a pro with everything from work separates to weekend attire. We're big fans of its ankle-cut shaft and comfortably rounded toe, and you're sure to appreciate the stacked...
The Barrington boot looks tough and is ready for daily use. The leather upper features a nylon panel for true flexibility, while a lace-up closure ensures a snug fit. A padded insole and thick rubber tread deliver fatigue-free wear.
Inspired by the land down under, the Gold Wallaby chukka from Sperry, will see you safely and stylishly through all types of weather and terrain. This classic ankle boot is masterfully crafted with a stain-and-water resistant leather upper and genuine deerskin lining inside. Plus your foot luxuriates on a full length, triple density footbed with memory foam for even greater comfort. A...
Simple, timeless, and effortlessly cool, the Barnes chukka from GUESS by Marciano is a go-to boot you can dress up or down. Its suede upper gives it a luxe look and feel, while its cushioned insole and rubber outsole make it comfortable enough for everyday campus or dress-casual office wear.
This handsome Gold chukka boot from Sperry Top-Sider offers classic good looks with its supple leather upper and neat lacing. The padded footbed provides cushioning comfort, and the siped rubber outsole flexes with every laid-back step.
You'll love the uniqueness in GUESS's Coltan. This leather lace up has contrast stitching and a double-layered shaft for various styling options. The rubber sole provides support and traction for all-day wear.
This classic boot from Sperry Top-Sider is an easy choice for everyday. The grainy leather boot features elastic panels for a custom fit, handsome stitching details, and a padded footbed to keep you in comfort. Rubber grips on the sole make every step steady.