Mens Casual Chukka Boots

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Clarks Desert® Boot

Clarks Desert® Boot - Beeswax Leather (Men's)
 
$119.95 Free Shipping Both Ways!
 
Clarks Desert® Boot

Clarks Desert® Boot - Sand Suede (Men's)
 
$119.95 Free Shipping Both Ways!
 
Clarks Desert® Boot

Clarks Desert® Boot - Brown Suede (Men's)
 
$119.95 Free Shipping Both Ways!

Clarks Desert® Boot

Clarks Desert® Boot - Black Suede (Men's)
 
$119.95 Free Shipping Both Ways!
 
Clarks Desert® Boot

Clarks Desert® Boot - Black Suede/Yellow Pop (Men's)
 
$119.95 Free Shipping Both Ways!
 
Clarks Desert® Boot

Clarks Desert® Boot - Grey Leather (Men's)
 
$119.95 Free Shipping Both Ways!

Clarks Desert® Boot

Clarks Desert® Boot - Oakwood Suede (Men's)
 
$119.95 Free Shipping Both Ways!
 
Clarks Desert® Boot

Clarks Desert® Boot - Off White Nubuck/Brown Pop (Men's)
 
$119.95 Free Shipping Both Ways!
 
Clarks Desert® Boot

Clarks Desert® Boot - Off White Nubuck/Celery Pop (Men's)
 
$119.95 Free Shipping Both Ways!

Clarks Desert® Boot

Clarks Desert® Boot - Taupe Distressed (Men's)
 
$119.95 Free Shipping Both Ways!
 
Clarks Bushacre 2

Clarks Bushacre 2 - Beeswax Leather (Men's)
 
$84.95 Free Shipping Both Ways!
 
Clarks Bushacre 2

Clarks Bushacre 2 - Black Suede (Men's)
 
$84.95 Free Shipping Both Ways!

Clarks Bushacre 2

Clarks Bushacre 2 - Brown Suede (Men's)
 
$84.95 Free Shipping Both Ways!
 
Clarks Bushacre 2

Clarks Bushacre 2 - Dark Brown Leather (Men's)
 
$84.95 Free Shipping Both Ways!
 
Clarks Bushacre 2

Clarks Bushacre 2 - Grey Suede (Men's)
 
$84.95 Free Shipping Both Ways!

Clarks Bushacre 2

Clarks Bushacre 2 - Sand Suede (Men's)
 
$84.95 Free Shipping Both Ways!
 
Clarks Bushacre 2

Clarks Bushacre 2 - Steel Blue Suede (Men's)
 
$84.95 Free Shipping Both Ways!
 
Hush Puppies Bridgeport

Hush Puppies Bridgeport - Taupe Suede (Men's)
 
$99.95 Free Shipping Both Ways!

Hush Puppies Bridgeport

Hush Puppies Bridgeport - Black Suede (Men's)
 
$99.95 Free Shipping Both Ways!
 
Hush Puppies Bridgeport

Hush Puppies Bridgeport - Black Leather (Men's)
 
$99.95 Free Shipping Both Ways!
 
Hush Puppies Bridgeport

Hush Puppies Bridgeport - Classic Taupe Suede (Men's)
 
$99.95 Free Shipping Both Ways!

Red Wing Heritage 3141 - Work Chukka

Red Wing Heritage 3141 - Work Chukka - Brown Briar Oil Slick Leather (Men's)
 
$249.95 Free Shipping Both Ways!

 
Clarks Wallabee

Clarks Wallabee - Beeswax Leather (Men's)
 
$149.95 Free Shipping Both Ways!
 
Clarks Wallabee

Clarks Wallabee - Black Leather (Men's)
 
$149.95 Free Shipping Both Ways!

Clarks Wallabee

Clarks Wallabee - Brown Oily Leather (Men's)
 
$149.95 Free Shipping Both Ways!
 
Clarks Wallabee

Clarks Wallabee - Sand Suede (Men's)
 
$149.95 Free Shipping Both Ways!
 
Timberland Earthkeepers® City Premium Chukka

Timberland Earthkeepers® City Premium Chukka - Red Brown Full Grain Leather (Men's)
 
$184.95 Free Shipping Both Ways!

Clarks Wallabee Boot

Clarks Wallabee Boot - Beeswax Leather (Men's)
 
$159.95 Free Shipping Both Ways!
 
Clarks Wallabee Boot

Clarks Wallabee Boot - Black Leather (Men's)
 
$159.95 Free Shipping Both Ways!
 
Clarks Wallabee Boot

Clarks Wallabee Boot - Black Suede (Men's)
 
$159.95 Free Shipping Both Ways!

Clarks Wallabee Boot

Clarks Wallabee Boot - Brown Oily Leather (Men's)
 
$159.95 Free Shipping Both Ways!
 
Clarks Wallabee Boot

Clarks Wallabee Boot - Brown Suede (Men's)
 
$159.95 Free Shipping Both Ways!
 
Clarks Wallabee Boot

Clarks Wallabee Boot - Sand Suede (Men's)
 
$159.95 Free Shipping Both Ways!

Clarks Wallabee Boot

Clarks Wallabee Boot - Taupe Distressed (Men's)
 
$159.95 Free Shipping Both Ways!
 
Timberland Classic TBL® Chukka

Timberland Classic TBL® Chukka - Wheat Nubuck Leather (Men's)
 
$134.95 Free Shipping Both Ways!
 
Timberland Classic TBL® Chukka

Timberland Classic TBL® Chukka - Black Smooth Leather (Men's)
 
$134.95 Free Shipping Both Ways!

Mens Casual Chukka Boots

1-36 of 242 results   1 2 3 4 5  Next »
Dunham Reed
Great...but March 12, 2013
Reviewer: Daniel from Somerville, MA
I bought these because they are waterproof and I love my Dunham boots with the same sole. Sadly, once "weather" started I found that though they are waterproof the sole is slick in a frightening way. Luckily I had some snow spikes with me or I would not have made it out of my neighborhood based on the ice.They are super comfortable and I really like the look but as for safety I would mark them down.
Wears this shoe: Anywhere not wet
Timberland Baluster Chukka
Great SHOE/BOOT & Style! March 07, 2013
Reviewer: KAT from MI / but son-in-law in Raleigh NC
I bought these as a birthday gift for my son-in-law. He loves them so much that he wants to wear them every day!! He said they fit absolutely perfectly. He is a size 11.5. He turned 30 for his birthday. He loves the style and everything about them.
Wears this shoe: Dress up or down w/ jeans.
Red Wing Heritage 3141 - Work Chukka
Great shoes! February 26, 2013
Reviewer: SunnyNight from New York
Best shoes I've ever owned. Quality is top notch. The design of the shoes is reminiscent of the depression era. It may take a while for these shoes to break in. The sole of the shoe was really hard when I first got them. As for the design of the sole itself? Classic Red Wing!
Wears this shoe: Everyday
Clarks Desert® Boot
Not as good as the original...but pretty close February 14, 2013
Reviewer: LBI GUY from Verona, NJ
This are great shoes. Bring back alot of memories. They are comfortable and perfect with cords, khaki's and jeans.
Wears this shoe: Casual wear
Andrew Marc Greenwich
Andrew Marc Shoe Review February 13, 2013
Reviewer: Sam from Alb. NM
These boots are of overall good quality. They look good and the pictures represent them well. The only reservation I have with them is the heel. It's a little low for my taste and seems to be made from hard plastic with a rubber cap, so they are noisy when you walk. I might consider changing out the heels for a softer stacked leather and have them a little taller. But overall I'm satisfied. They're good for casual office wear, a night out or just everyday use.
Wears this shoe: At the office or out to dinner