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Evocatively named 'Explorer', these Chukka boots from Frye are perfect for wearing on adventurous... more details
$406.39
Stride on the finer edge of casual in these leather and suede chukka boots from Stacy Adams. more details
Designed for sturdy style, these lace-up boots from Kenneth Cole Reaction offer all-day comfort... more details
$238.65
Ruggedly stylish and incredibly versatile, these cap-toe boots from Rockport are designed with a... more details
Perfect for work or play, these sturdy lace-up boots from Frye are styled in rich leather and... more details
A shoe that compliments any ensemble, these classic chukkas in leather from Rockport offer a... more details
Rugged takes on whole new meaning with these handsome Lumber Up boots-built sturdy and... more details
$170.47
Made from a waterproof pull up and vintage leather upper, the lug bottom hiker boot from Frye... more details
$351.84
Survive the wet weather in a pair of classic duck boots from Sperry Top-Sider. more details
$150.01
I. n. c. International Concepts introduces an industrial edge to your casual look with the Ivan... more details
Eastland Shoe sends you to the great outdoors with full comfort and protection in these casual... more details
$177.28
Cole Haan combines modern technology and classic style to create the superior comfort and... more details
$436.39
Kenneth Cole Reaction uses multi-media styling to create the chic look of these cool-casual boots... more details
Hand-sewn moccasin construction adds traditional comfort and style to the 1955 Boots by Eastland. more details
$306.84
Dress up these Clarks men's limited edition tweed Bushcare boots with a classic sport coat and... more details
$135.37 (10% off)
Full-grain leather and top-stitch detailing create the finely styled uppers of the Sanborn chukka... more details
$203.20
This footwear classic originated in 1965 when Lance Clark sketched out a moccasin built on our... more details
$166.12
Side gore makes for easy on and off with these smooth leather boots with an ankle-high profile... more details
$190.92
An international cult classic, the Desert Boot was inspired by the crepe-soled boots worn by... more details
$124.58
Recognizable for its signature center stitched seam, the Desert Trek has been a footwear classic... more details
Cole Haan's classic Chelsea in waterproof leather uppers feature an innovative rubber unit... more details
Frye's Ashland chukkas are made from smooth full-grain leather and have a hardy stitch-out... more details
$379.12
The Callan boots from Alfani complement your modern look with the futuristic flair of their... more details
$147.68 (10% off)
The Pinch Rugged chukkas from Cole Haan are designed with a Grand. Os footbed for increased... more details
$245.47
Sophisticated and stylish, these lace-up boots from Steve Madden feature a cap toe and pieced... more details
The Kooper boots from Alfani feature top-stitch detailing and a side-zip closure at the upper for... more details
$123.06 (10% off)
A classic chukka silhouette gets energized by I. n. c. International Concepts and the addition of... more details
Take your look in a retro direction with the vintage styling of these casual Chukka boots from... more details
$334.11
A standout style, these ultra-cool Clarks men's camo Bushacre boots are a limited edition. more details
Plush suede covers the upper of the Dustin boots from Alfani, reimagining the classic Chelsea... more details