This three-eyelet chukka boot is versatile enough for the office or the weekend. 100% Canvas. rubber sole. Breathable canvas. Flexable sole. Non-marking outsole. Ethylene vinyl acetate comfort footbed.
$41.35
$60.00
Find comfort, quality and style in the Corbin Boot. It features a durable upper, laces for good fit, mesh lining, Dexter's signature Comfort Insole for all-day support, and a textured outsole. Manmade materials.
$59.99
$59.99
Meet the new Clarks Originals Montacute Duke men's lace-up boot. Made with the highest quality full-grain leather upper, this shoe also features a fabric and PU lining, as well as a steel shank and Ortholite molded footbed that was designed with your comfort in mind to help you feel less fatigue throughout the day. ...
$75.99
$75.99
Get the support and toughness you need in the Eastland Haystack outdoor boot. This mid-cut men's hiking boot features a mesh and suede upper with a bellows tongue to keep out debris as you scramble. A padded collar and tongue and a combination lacing closure ensure comfortable, personalized fit. An OrthoLite-cushioned ...
$90.21
$100.00
With a relaxed two-eye design and plush suede upper, the Tommy Hilfiger Sten chukka is the key to looking smart and polished on your days off.
$59.49
$59.49
Rugged with distinctive character. Stand out in a pair of Hoover lace-up boots from Bed Stu.
$138.59
$145.00
Refined and handsome style comes in the Mark Nason SKECHERS Morley boot. Smooth premium leather upper in a lace up dress casual plain toe chukka ankle boot with stitching and overlay accents. Memory Foam insole, light flexible outsole.
$110.00
$110.00
Rugged and perfect for everyday wear, the new Clarks Original Varick Hill men's boot is the perfect addition to any closet. You can pair these boots with just about any casual outfit and fit right in! Crafted with a full-grain leather and textile upper, these boots also feature a breathable fabric and cow suede ...
$104.90
$104.90
Chukka
$62.29
$62.29
This handsome leather boot performs as well in the field as it does around town.
$123.42
$139.99
Lace-up front closure with pull tab at heel for easy on-and-off wear. Closed toe. Contrast topstitching. Smooth textile lining and cushioned adiPRENE® footbed provide all-day comfort and support. Durable rubber lug outsole. Imported.
$45.80
$45.80
Look sharp rain or shine in the Timberland Britton Hill Waterproof Chukka. This casual boot features a combination of full-grain and nubuck leather for a stylish contrast and with the waterproof membrane and GripstickTM rubber outsole, these boots will perform great in any weather condition.
$176.75
$180.00
Put your best foot forward in the handsomely finished Florsheim Indie Cap Boot. The milled leather upper of this casually elegant men's lace-up boot offers durable style. A leather lining and cushioned footbed lend all-day interior comfort. The Florsheim Indie Cap Boot rests atop a sturdy rubber sole for lasting wear.
$174.95
$175.00
Urban wanderer or country gentleman, you'll love the combination of style and protection provided by the Rockport Gentlemen's Boot Waterproof Moc Mid boot. Made from waterproof full grain leather with seam-sealed Hydro-Shield� construction, this men's ankle boot includes a DEWIX textile lining to also keep you dry and ...
$149.95
$149.95
Steve Madden, the company, was founded by Steve Madden, the man, in 1990 in Brooklyn, where he started out making trend-advancing shoes one pair at a time. It was not long after that the Steve Madden focus on "now-ness" earned rave reviews from young female fans mad for the funky, chic, and yet competitively priced ...
$80.90
$115.00
Give your urban look a bit of an 'edge' with this hard-wearing men's boot. Designed for tackling any environment head on, its direct-injected sole provides flexible grip and outstanding support all day long.
$129.99
$129.99
Distressed leather lends rustic sophistication to this handsome FRYE chukka.
$378.00
$378.00
Own the night with the Stacy Adams Cagney lace-up boot. This sleek men's lace-up has a supple leather upper for a cool, sophisticated look. The Suedetec lining lends breathability, while the cushioned footbed delivers sublime comfort. The flexible rubber sole of the Stacy Adams Cagney carries you with traction and ...
$99.95
$99.95
Showcase your style and stay comfortable with the Timberland Britton Hill Chukka boot.
$180.00
$180.00
John Varvatos employs worn-in details to lend a vintage look to this chukka boot.
$198.00
$198.00