Durable comfort and classic style come together in the Timberland Tremont Chukka boot. Crafted with a supple leather upper, this men's ankle boot is versatile and ready to take on the day. Underfoot, an OrthoLite footbed lends all-day interior ease, while the Green RubberTM sole features partially recycled material ...
$94.90
$125.00
Embrace the classic look and sleek versatility of the Rockport Ledge Hill Too Chukka boot, a handsome addition to any dress-casual wardrobe. This men's lace-up desert boot features a full grain leather or suede upper with a three-eye lace closure plus a touch of padding at the topline. The recycled polyurethane ...
$150.00
$150.00
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$41.98
$41.98
Timberland West Haven City 2.0 Chukka Boots
$120.39
$160.00
The Briggs is back, and this time in a coveted ankle height boot for men. Outdoorsy and rustic, yet sophisticated and smart, the Briggs Mid WP men''s boot keeps you comfortable and dry thanks to the KEEN.DRY waterproof, breathable membrane and oiled nubuck leather upper. The recycled foam footbed and EVA midsole on ...
$111.95
$140.00
Suede chukka
$70.00
$70.00
Get back to basics with the Rockport Main Route Northfield Plain Toe Boot. Simply styled for casual versatility, this men's ankle boot goes the distance with a Hydro-ShieldTM waterproof leather upper, five-eye lace and padded tongue and collar. A cushioned footbed offers interior comfort to the Rockport Main Route ...
$96.44
$125.00
These new Boots from Levi's are a Jax of all trades!
$89.95
$89.95
Pair these stylish Levi's; boots with jeans, or your favorite cut-off shorts for impeccable style.
$42.99
$80.00
Spring time vibes are all good with the Lex II boot from Levi's!
$85.00
$85.00
Dress it up with the Timberland 9062B Earthkepers Revenia Chukka! These premium suede chukkas have a durable water-based water repellent that creates a barrier of protection. They also feature 100% organic cotton laces, 100% recycled PET ReCanvas linings, genuine leather welts, OrthoLite PU footbeds, and hand-stained ...
$100.00
$100.00
Crisp and classic, this casual chukka from Sebago offers impeccable style.
$47.99
$155.00
Teva was born in the grand canyon back in 1984, when a river guide rigged two velcro watchbands to an old pari of flip flops and created a shoe that wouldn't float away. Three decades later, we've grown up into an icon of comfort and utilitarian style
$44.64
$44.64
Achieve a laid-back look that packs plenty of ruggedness with the 3875 Soft Paw Chukka boot from Irish Setter. The casual, full grain leather upper features a padded collar to help prevent blisters. The leather-covered memory foam footbed provides cushioning, while the ScentBanTM technology keeps feet fresh by ...
$144.04
$174.99
Chukka
$97.61
$125.00
Be ready for your weekend in the Camp Chukka Boot by Minnetonka Moccasin.Leather upper in a casual chukka boot styleLace-up frontLeather lining with a cushioning footbedDecorative stitching accentTraction outsole
$75.98
$99.95
Meet the new Clarks Bushwish Mid Boot, the boots that are both stylish and comfy! Made with an incredibly comfortable and removable Ortholite and open cell PU sheet footbed, that allows for heel and arch support, giving you that added all-day comfort. This boot also features a steel shank, as well as full-grain ...
$83.94
$83.94
Jayy is a lace-up ankle boot with a cap toe and contrast stitching.
$100.00
$100.00
Caterpillar 6" Transform Boot has a smooth, non - industrial look. It's a stylish new look for work, or regular rugged activity! Choose between oiled nubuck or full - grain leather uppers on this casual - but - sturdy Transform Boot from Cat. Boasts nylon mesh lining and a molded EVA sock liner for comfort, every step ...
$69.81
$85.00
FEATURES of the Timberland Men's Bradstreet Plain Toe Chukka Shoe Premium full-grain and nubuck leathers from an LWG Silver-rated tannery provide comfort and durability 100% organic cotton laces Extra-soft 100% recycled PET lining and footbed cover for exceptional comfort OrthoLite PU footbed made from 5% recycled ...
$77.99
$125.00