Skip Navigation
Shopping Bag [0]Checkout
  • There are currently no items in your Shopping Bag.

Buy online & pick up in store.
Main Content

Men's Chukka Shoes Extended Sizes

Narrow by:
UGG® 'Leighton' Chukka Boot (Men)
UGG® 'Leighton' Chukka Boot (Men)
UGG® 'Leighton' Chukka Boot (Men)Was: $159.95Now: $103.9035% OFF
Timberland Earthkeepers® 'Britton Hill' Cap Toe Chukka Boot (Men)
Timberland Earthkeepers® 'Britton Hill' Cap Toe Chukka Boot (Men)
Timberland 'Wodehouse Lost History' Boot (Men)
Timberland 'Wodehouse Lost History' Boot (Men)
1901 'Andres' Chukka Boot (Men)
1901 'Andres' Chukka Boot (Men)
Florsheim 'Jet' Chukka Boot
Florsheim 'Jet' Chukka Boot
Price MatchedFlorsheim 'Jet' Chukka BootWas: $135.00Now: $101.9920% OFF
Rated 4.6 out of 5 stars with(10) reviews
Tod's 'Quinn' Ankle Boot
Tod's 'Quinn' Ankle Boot
Andrew Marc 'Woodside' Chukka Boot (Men)
Andrew Marc 'Woodside' Chukka Boot (Men)
Andrew Marc 'Woodside' Chukka Boot (Men)Was: $218.00Now: $109.9050% OFF
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
Clarks® Originals 'Desert' Boot (Men)
Clarks® Originals 'Desert' Boot (Men)
Clarks® Originals 'Desert' Boot (Men)Was: $130.00Now: $77.9040% OFF
UGG® 'Alin' Twinsole® Chukka Boot (Men)
UGG® 'Alin' Twinsole® Chukka Boot (Men)
UGG® 'Alin' Twinsole® Chukka Boot (Men)Was: $149.95Now: $96.9035% OFF
ECCO 'Dublin' Chukka Boot (Men)
ECCO 'Dublin' Chukka Boot (Men)
New MarkdownECCO 'Dublin' Chukka Boot (Men)Was: $199.95Now: $119.9640% OFF
UGG® 'Lyle' Chukka Boot (Men)
UGG® 'Lyle' Chukka Boot (Men)
Timberland 'City Lite' Waterproof Chukka Boot (Men)
Timberland 'City Lite' Waterproof Chukka Boot (Men)
Frye 'James' Lug Sole Chukka Boot (Men)
Frye 'James' Lug Sole Chukka Boot (Men)
Timberland Earthkeepers® 'Groveton' Chukka Sneaker (Men) (Online Only)
Timberland Earthkeepers® 'Groveton' Chukka Sneaker (Men) (Online Only)
Clarks® Originals 'Desert' Boot (Men)
Clarks® Originals 'Desert' Boot (Men)
Clarks® Originals 'Desert' Boot (Men)Was: $140.00Now: $83.9040% OFF
Clarks® Originals 'Desert' Boot (Men)
Clarks® Originals 'Desert' Boot (Men)
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
1901 'Hayward' Chukka Boot (Men)
1901 'Hayward' Chukka Boot (Men)
Red Wing 'Classic' Chukka Boot
Red Wing 'Classic' Chukka Boot
Calvin Klein 'Ballard' Suede Chukka Boot (Men)
Calvin Klein 'Ballard' Suede Chukka Boot (Men)
Deer Stags 'Seattle' Leather Chukka Boot (Men)
Deer Stags 'Seattle' Leather Chukka Boot (Men)
Volcom 'Del Mesa' Suede Chukka Boot (Men)
Volcom 'Del Mesa' Suede Chukka Boot (Men)
Volcom 'Del Mesa' Chukka Boot (Men)
Volcom 'Del Mesa' Chukka Boot (Men)
Andrew Marc 'Dorchester' Suede Chukka Boot (Men)
Andrew Marc 'Dorchester' Suede Chukka Boot (Men)
Andrew Marc 'Dorchester' Suede Chukka Boot (Men)Was: $198.00Now: $117.9040% OFF
TOMS 'Mateo' Chukka Boot (Men)
TOMS 'Mateo' Chukka Boot (Men)
New MarkdownTOMS 'Mateo' Chukka Boot (Men)Was: $119.00Now: $71.4040% OFF
Børn 'Asten' Chukka Boot (Men)
Børn 'Asten' Chukka Boot (Men)
Tommy Bahama 'Relaxology Collection - Riker' Chukka Boot (Men)
Tommy Bahama 'Relaxology Collection - Riker' Chukka Boot (Men)
Blondo 'Gustave' Waterproof Chukka Boot (Men)
Blondo 'Gustave' Waterproof Chukka Boot (Men)
Florsheim 'Doon' Chukka Boot (Men)
Florsheim 'Doon' Chukka Boot (Men)
Ermenegildo Zegna Deerskin Chukka Boot (Men)
Ermenegildo Zegna Deerskin Chukka Boot (Men)
Børn 'Jax' Chukka Boot (Men)
Børn 'Jax' Chukka Boot (Men)
Andrew Marc 'Standard' Chukka Boot (Men)
Andrew Marc 'Standard' Chukka Boot (Men)
UGG® 'Alin' Tweed Chukka Boot (Men)
UGG® 'Alin' Tweed Chukka Boot (Men)
Lanvin High Top Sneaker (Men)
Lanvin High Top Sneaker (Men)
Merrell 'Realm' Chukka Boot (Men)
Merrell 'Realm' Chukka Boot (Men)
Dunham 'REVdash' Chukka Boot (Men)
Dunham 'REVdash' Chukka Boot (Men)
Lloyd 'Vadim' Chukka Boot (Men)
Lloyd 'Vadim' Chukka Boot (Men)
Ted Baker London 'Torsdi 2' Chukka Boot (Men)
Ted Baker London 'Torsdi 2' Chukka Boot (Men)
Ermenegildo Zegna 'Newport' Perforated Chukka Boot (Men)
Ermenegildo Zegna 'Newport' Perforated Chukka Boot (Men)
Giorgio Armani Woven Chukka Sneaker (Men)
Giorgio Armani Woven Chukka Sneaker (Men)
Lloyd 'Speed' Chukka Boot (Men)
Lloyd 'Speed' Chukka Boot (Men)
Blundstone Footwear Chukka Boot (Men)
Blundstone Footwear Chukka Boot (Men)
Florsheim 'Doon' Chukka Boot (Men)
Florsheim 'Doon' Chukka Boot (Men)
Ermenegildo Zegna Suede Chukka Boot (Men)
Ermenegildo Zegna Suede Chukka Boot (Men)
Rockport 'Ledge Hill 2' Chukka Boot (Men)
Rockport 'Ledge Hill 2' Chukka Boot (Men)
H by Hudson 'Cruise' Chukka Boot (Men)
H by Hudson 'Cruise' Chukka Boot (Men)
Lloyd 'Spider' Chukka Boot
Lloyd 'Spider' Chukka Boot
Lloyd 'Varello' Chukka Boot
Lloyd 'Varello' Chukka Boot
Santoni 'Urban' Chukka Boot
Santoni 'Urban' Chukka Boot
To Boot New York 'Layton' Chukka Boot Sneaker (Men)
To Boot New York 'Layton' Chukka Boot Sneaker (Men)
J&M 1850 'Hopson' Suede Chukka Boot (Men)
J&M 1850 'Hopson' Suede Chukka Boot (Men)
New MarkdownJ&M 1850 'Hopson' Suede Chukka Boot (Men)Was: $235.00Now: $140.9840% OFF
Joe's 'Slick' Suede Chukka Boot (Men)
Joe's 'Slick' Suede Chukka Boot (Men)
Joe's 'Slick' Suede Chukka Boot (Men)Was: $175.00Now: $104.9640% OFF
Trask 'Buckhorn' Leather Chukka Boot (Men)
Trask 'Buckhorn' Leather Chukka Boot (Men)
Trask 'Buckhorn' Leather Chukka Boot (Men)Was: $475.00Now: $355.9025% OFF

No items match all your filter selections.

Clear all to see unfiltered results.