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Frye's Ashland chukkas are made from smooth full-grain leather and have a hardy stitch-out... more details
$379.12
Frye's rugged heritage boots feature a smooth upper in vegetable-tanned leather and are fitted... more details
$624.59
Cole Haan updates the iconic Original Grand in a chukka boot for cooler weather, styled with... more details
$245.47
Frye Men's Ben Cap-Toe leather boots add a modern look to your casualwear in premium leather. more details
Kenneth Cole completes your modern casual style with these sleek ankle-high chukka boots in... more details
Perfect for work or play, these sturdy lace-up boots from Frye are styled in rich leather and... more details
Originally designed to help rodeo cowboys rope calves in competition, Frye's roper boots are... more details
$515.49
Special technology helps regulate your foot temperature inside these ankle-high leather boots... more details
Take your look in a retro direction with the vintage styling of these casual Chukka boots from... more details
$334.11
Made from a waterproof pull up and vintage leather upper, the lug bottom hiker boot from Frye... more details
$351.84
The Corazon Chukka boots from Carlos by Carlos Santana combine a flexible and lightweight... more details
$216.83
You like to move and so does this boot from Dr. Scholl's. A Chelsea-style profile with an... more details
$170.47
Cole Haan presents the elegance of a chukka silhouette in smooth buttery leather at the upper,... more details
$204.56
Supremely comfortable and incredibly cool, these slip-on boots from Eastland feature special... more details
$190.92
Frye presents their interpretation of a classic Chukka silhouette in supple leather and featuring... more details
Designed to keep your grip secure, these antiqued pull-up Italian leather boots from Frye have a... more details
$406.39
A foam-cushioned footbed and midsole contribute to the comfortable fit of these stylish... more details
$244.11
Dip-dye styling at the upper takes these smooth leather Chelsea boots from Frye to the next level... more details
Full-grain leather and top-stitch detailing create the finely styled uppers of the Sanborn chukka... more details
$203.20
Eastland Shoe sends you to the great outdoors with full comfort and protection in these casual... more details
$177.28
Buckle details introduce the perfect amount of edge to these over-the-ankle boots in leather from... more details
$197.74
The Ludlow shoes from Frye resemble sleek chukka boots but feature a high-top sneaker profile and... more details
$174.56
Cole Haan's classic Chelsea in waterproof leather uppers feature an innovative rubber unit... more details
$436.39
Eastland uses their signature Active Memory Foam to achieve the all-day comfort of these stylish... more details
The 'Murray' lace-up boots from Frye have been made from supple dip-dyed leather that adapts to... more details
A shiny finish and metal ornament detail create the super-glamourous look of these moc-toe boots... more details
$811.42
This pair of men's boots is a comfortable no-brainer for your everyday wardrobe. These classic... more details
Soft suede at the upper introduces a luxurious look and feel to these classic Chelsea boots by... more details
$238.65
The Terra boots from Frye only get better the more you wear them. Designed with convenient... more details
The Colvins from Kenneth Cole offer the cool high-top silhouette of a sneaker with the smooth... more details