Designed for looks and built for comfort, this men’s lace-up boot from the Tor collection has everything you need for your busiest–and most stylish–days. It’s made of rich leather in black with a breathable waterproof GORE-TEX lining. The removable cork and Ortholite footbed cushions and supports, while its heavy-duty rubber outsole offers traction and another layer of cushioning. Perfect with slacks, denim, and cords.

An international cult classic, the iconic men’s Desert Boot by Clarks Originals was inspired by crepe-soled boots worn by British officers in World War II. Crafted from natural materials including sandstone/brown suede for supreme comfort, its timeless styling has remained unchanged for over 60 years.

Clarks Originals Desert Boot

Stay comfortable with the Dunham Windsor Mid Cut Boot. The waterproof leather upper of this men’s casual boot has a Tectonic TongueTM for an increased range of motion. The Rollbar enhances stability, while a premium insert absorbs shock for comfort. A rubber sole with multi-directional Tru-Trak treads offers the Dunham Windsor Mid Cut Boot excellent traction.

Volcom Del Mesa boots. The deconstructed Chukka styling of the Del Mesa Shoe screams casual comfort. Asymmetrical details paired with a direct attached molded circle stone and multi-color detailing make this an eye catcher and the RCFTM technology plus compression molded EVA outsole crank up the comfort. Approx shaft height: 4.5″(11.5cm). Imported.

Be classically stylish in the Ulysses Chukka Boot by Calvin Klein.Suede upper in a casual chukka boot styleRound toeLace up frontSmooth lining with a cushioning footbedDecorative stitching and overlaysTraction outsole1 inch heel

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 footwear it produced. The company popularized the “dressy sneaker,” and continues to man the forefront of trends.

Get relaxed style with the Clarks Stinson Hi ankle boot. This men’s Wallabee-inspired ankle boot features a suede or leather upper with tonal laces for a snug fit; moccasin-style contrast stitching details create a rich, textured look. The foam-cushioned footbed and EVA midsole keep you comfortable and supported, while a natural crepe rubber sole delivers traction to the Clarks Stinson Hi boot.

Get relaxed style with the Clarks Stinson Hi ankle boot. This men’s Wallabee-inspired ankle boot features a suede or leather upper with tonal laces for a snug fit; moccasin-style contrast stitching details create a rich, textured look. The foam-cushioned footbed and EVA midsole keep you comfortable and supported, while a natural crepe rubber sole delivers traction to the Clarks Stinson Hi boot.

One of the most iconic silhouettes in mens footwear, the Channing chukka boot delivers casual sophistication with just a dash of attitude.

This modern high fashion dress boot by Steve Madden will be a show stopper this season.

Sometimes less is more. ThereÆs a simple shoe solution to all of your wardrobe problems. With its smooth leather and classic, clean design, the Casey Chukka Boot is all you need.

There’s nothing traditional about this men’s low-cut boot. Crafted of leather, suede, and fabric, it has a design that’s a little rugged and a little urban, with a heavy dose of cool. The lace-up closure ensures a snug fit, while the breathable mesh lining, removable Ortholite footbed, and durable rubber outsole provide all-over comfort for long-term wear. Wear it with denim or any casual pant. Synthetic lining. EVA sole.

Deconstructed to utter simplicity for a natural feel and a clean, uncluttered look, the Woolrich Lane chukka is the epitome of casual style. Featuring an upper of premium Charles F. Stead suede with minimal stitching, this men’s desert boot has a die-cut wool footbed for moisture-wicking support, while a lugged rubber sole provides reliable traction.

strobel cement construction, water resistant uppers, padded leather and fabric footbed, rubber outsole

A timeless design for a well-appointed casual wardrobe, the Stacy Adams Astro chukka brings a refined panache along with lightweight comfort. Featuring an upper of rich suede, this men’ chukka boot has a simple moc-toe design and two-eyelet lacing for a slightly rustic appeal. A cushioned footbed provides interior support, while the lightweight EVA sole gives the Stacy Adams Astro moc-toe chukka secure traction and an easygoing step to complement your casual style.

Chukka Boot – Men’s

Men’s Rockport, Charson Chukka Boots You?ll admire these amazing chukkas! Leather upper Lace up closure for a secure fit Soft fabric lining Removable cushioned footbed for added comfort Adiprene by Adidas sport technology for added shock absorption in the heel manmade outsole. Heel Height of 0.75 inches

Waterproof and lightweight, the City Smart Waterproof Collection is perfect for when the weather’s not on your side but you still need style. Built with Hydro-ShieldTM waterproof construction, a shock-absorbing PU sole, anti-microbial DEWIX wicking linings, and ADIPRENE by adidas, you are sure to stay dry and comfortable no matter what. The PU outsole provides durable shock absorption to help reduce foot fatigue, while the sponge EVA footbed conforms to the shape of the foot for a personalized fit and ADIPRENE ® by adidas provides shock absorbing heel cushioning. DEWIX anti-microbial linings help reduce foot odor and wick moisture to help keep the foot dry, and Hydro-Shield construction with waterproof leather, seam sealed, waterproof insole, and gusseted tongue helps keep feet dry in wet weather.

Moccasin meets desert boot in this rugged offering from FRYE.