Category: Chukka Boots

Rockport Men’s Ledge Hill 2 CH Chukka Boot,Black,14 M US

-12% Rockport Men’s Ledge Hill 2 CH Chukka Boot,Black,14 M US

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 ...

$149.95 $170.00

Rockport Men’s Rocsports Lite 2 Chukka Boot, Tan, 13 XW US

-9% Rockport Men’s Rocsports Lite 2 Chukka Boot, Tan, 13 XW US

Redefine the term "weekend warrior" in the Rockport RocSports Lite 2 Chukka boot. Modeled after the classic desert boot, this men's casual ankle boot has a premium nubuck or leather upper with a stretchy, padded collar and tongue for soft flex. The sponge EVA footbed molds to the contours of your foot and features ...

$109.95 $120.00

Stacy Adams Men’s Astro Chukka Boot,Sand Suede,9 M US

-1% Stacy Adams Men’s Astro Chukka Boot,Sand Suede,9 M US

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 ...

$89.95 $90.00

FRYE Men’s James Lug Chukka Boot,Black,9 M US

-55% FRYE Men’s James Lug Chukka Boot,Black,9 M US

Dress up for the office or a night out in a pair of chukka boots by Frye. These classic men's boots are made of antique scotch-grain leather in a traditional chukka silhouette. Goodyear welt construction and durable rubber outsole make them ideal for comfortable, all-day wear. Frye was founded in 1863 and is the ...

$149.38 $328.00

Woolrich Men’s Beebe Chukka Boot

Woolrich Men’s Beebe Chukka Boot

The Beebe is a lace-up chukka boot made from the highest quality materials. It features a full grain leather upper and wool liner. The wool liner is anti-microbial, all natural and heat regulating. Other features include leather welting, a comfort footbed and vibram outsole for traction and durability. For 180 years ...

$67.93 $67.93

Sebago Men’s Hamilton Lace-Up Boot

Sebago Men’s Hamilton Lace-Up Boot

Sebago Hamilton Casual Boots for the urban adventurer. Talk ahout all the good stuff rolled into one! I really prefer Boots to "just Shoes", but you have to put shoes into your footwear lineup as well. Looks to me as though Sebago combined the rugged look and feel of a Boot with detailing (Wing-Tip) that lets me have ...

$105.49 $105.49

Bed Stu Men’s Bryden Boot

Bed Stu Men’s Bryden Boot

Perfectly handsome and totally at ease, BED:STU's Bryden boot packs a ton of dapper style into a pint-sized package. This offering in leather sports sleek lines and an understated attitude that's effortlessly cool. A leather sole promises smooth moves wherever you go in BED:STU.

$69.99 $69.99

Clarks Men’s Darning Hi Chukka Boot, Grey, 10 M US

-62% Clarks Men’s Darning Hi Chukka Boot, Grey, 10 M US

Featuring a low-cut profile and premium leather upper, this men's lace-up boot from the Tor collection is a handsome addition to your wardrobe. It's lined in leather for reduced friction and has a cork footbed for advanced cushioning. The ground-gripping rubber outsole is durable for long-term wear. Goes with ...

$53.99 $140.00