Free Shipping. No Minimum.

Flat Heel Chukka Boots

Timberland Davis Square Fabric/Leather Chukka Boot (Men's)
New!
Sale
Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Medium Grey Nubuck/Cordura® Fiber
New
Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Navy Nubuck/Cordura® Fiber
New
Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Black Nubuck/Cordura® EcoMade Fiber
Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Wheat Nubuck/Cordura® EcoMade Fiber
$59.95 - $79.95
Keen Grayson Chukka Boot (Men's)
New!
Sale
Keen Grayson Chukka Boot(Men's) -Mid Brown/Scylum
Keen Grayson Chukka Boot(Men's) -Sage/Lama
$129.95
Twisted X Boots MDM0014 (Men's)
New!
Sale
Twisted X Boots MDM0014(Men's) -Copper Leather
$104.99
Nunn Bush Ozark Plain Toe Chukka Boot (Men's)
New!
Sale
Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Black Tumble Leather
Sale
Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Brown Chamois Leather
Sale
Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Rust Leather
Sale
Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Tan Chamois Leather
Sale
$75.95
$95.00 20% off
ECCO Crepetray Chukka Boot (Men's)
New!
Sale
ECCO Crepetray Chukka Boot(Men's) -Lion/Powder Cow Leather/Cow Nubuck
Sale
$135.99
$170.00 20% off
Timberland FlyRoam Go Lace Chukka Boot (Women's)
New!
Sale
Timberland FlyRoam Go Lace Chukka Boot(Women's) -Jet Black Escape/Natural Sandune
Sale
Timberland FlyRoam Go Lace Chukka Boot(Women's) -Pure Cashmere Escape/Natural Sandune
Sale
$94.95
$120.00 21% off
UGG Canoe Water Resistant Chukka Boot (Children's)
New!
Sale
UGG Canoe Water Resistant Chukka Boot(Children's) -Black Leather
Sale
UGG Canoe Water Resistant Chukka Boot(Children's) -Charcoal Leather
Sale
$48.95
$65.00 25% off
Eastland Seneca (Women's)
New!
Sale
Eastland Seneca(Women's) -Khaki Suede
Eastland Seneca(Women's) -Natural Leather
Eastland Seneca(Women's) -Peanut Leather
Eastland Seneca(Women's) -Tan Waxee Leather
$99.95
Clarks Un.Astin Chukka Boot (Women's)
New!
Sale
Clarks Un.Astin Chukka Boot(Women's) -Aubergine Cow Suede
Sale
Clarks Un.Astin Chukka Boot(Women's) -Black Cow Full Grain Leather
Sale
Clarks Un.Astin Chukka Boot(Women's) -Khaki Cow Full Grain Leather
Sale
$52.97 - $104.99
$150.00 up to 65% off
Nunn Bush Sal Chukka Boot (Men's)
New!
Sale
Nunn Bush Sal Chukka Boot(Men's) -Black Synthetic
New
Nunn Bush Sal Chukka Boot(Men's) -Brown Synthetic
New
$69.95
Nunn Bush Littleton Plain Toe Chukka Boot (Men's)
New!
Sale
Nunn Bush Littleton Plain Toe Chukka Boot(Men's) -Brown Leather
Sale
Nunn Bush Littleton Plain Toe Chukka Boot(Men's) -Tan Leather
Sale
$71.95
$90.00 20% off
Sperry Top-Sider Bahama Lug Naval Ankle Boot (Men's)
New!
Sale
Sperry Top-Sider Bahama Lug Naval Ankle Boot(Men's) -Black Canvas
Sale
$48.95
$69.95 30% off
White Mountain Anderson Chukka Boot (Women's)
New!
Sale
White Mountain Anderson Chukka Boot(Women's) -Cool Grey Smooth Synthetic
Sale
White Mountain Anderson Chukka Boot(Women's) -Tan Smooth Synthetic
Sale
$39.95
$79.00 49% off
ROBERT WAYNE Greyson Suede Chukka Boot (Men's)
New!
Sale
ROBERT WAYNE Greyson Suede Chukka Boot(Men's) -Cognac Suede
Sale
$54.97
$140.00 61% off
Nunn Bush Middleton Plain Toe Chukka Boot (Men's)
New!
Sale
Nunn Bush Middleton Plain Toe Chukka Boot(Men's) -Black Leather
Sale
Nunn Bush Middleton Plain Toe Chukka Boot(Men's) -Brown Leather
Sale
Nunn Bush Middleton Plain Toe Chukka Boot(Men's) -Cognac Leather
Sale
$75.95
$95.00 20% off
Crevo Alameda Chukka Boot (Men's)
New!
Sale
Crevo Alameda Chukka Boot(Men's) -Chestnut Leather
Crevo Alameda Chukka Boot(Men's) -Gray Suede
$79.95
Florsheim Navigator Chukka Boot Jr. (Boys')
New!
Sale
Florsheim Navigator Chukka Boot Jr.(Boys') -Brown Leather
New
Florsheim Navigator Chukka Boot Jr.(Boys') -Mocha Leather
New
Florsheim Navigator Chukka Boot Jr.(Boys') -Navy/Brown Leather
New
$64.95
Clarks Capler Mid Ankle Boot (Men's)
New!
Sale
Clarks Capler Mid Ankle Boot(Men's) -Sand Cow Suede
Sale
$65.00
$100.00 35% off
UGG Canoe HyperWeave Chukka (Children's)
New!
Sale
UGG Canoe HyperWeave Chukka(Children's) -White Wall Knit
Sale
$48.95
$75.00 35% off
Vans Prairie Chukka MTE (Women's)
New!
Sale
Vans Prairie Chukka MTE(Women's) -Black Leather/Birch
Sale
Vans Prairie Chukka MTE(Women's) -Tan/Black Leather
Sale
$47.95
$80.00 40% off
Umi Jared Chukka (Boys')
New!
Sale
Umi Jared Chukka(Boys') -Black Leather
$64.95
Umi Jared II Chukka (Boys')
New!
Sale
Umi Jared II Chukka(Boys') -Black Leather
Umi Jared II Chukka(Boys') -Cognac Leather
$69.95
ECCO Crepetray Chukka Boot (Women's)
New!
Sale
ECCO Crepetray Chukka Boot(Women's) -Amber Nubuck Leather
New
ECCO Crepetray Chukka Boot(Women's) -Black Nubuck Leather
New
ECCO Crepetray Chukka Boot(Women's) -Black/Powder Full Grain Leather
Sale
ECCO Crepetray Chukka Boot(Women's) -White/Powder Full Grain Leather
Sale
$103.45 - $169.95
$160.00 - $170.00 up to 35% off
Nunn Bush Nantucket Plain Toe Chukka Boot (Men's)
New!
Sale
Nunn Bush Nantucket Plain Toe Chukka Boot(Men's) -Black Leather
Sale
$71.95
$90.00 20% off
Nunn Bush Memphis St. Moc Toe Waterproof Boot (Men's)
New!
Sale
Nunn Bush Memphis St. Moc Toe Waterproof Boot(Men's) -Black Smooth Leather
Sale
$75.95
$95.00 20% off