Available 24/7 at (800) 927-7671

Join Zappos Rewards and Get Expedited Shipping!*

My Cart

“chukka” we found 1296 items!

Choose a
  • Product Type
to sort results
Show Filters
Salvatore Ferragamo - Charlie
Salvatore Ferragamo Charlie $695.00
LUXURY
View More Like This Jeffery-West - Deadwood
Jeffery-West Deadwood $675.00
LUXURY
View More Like This Salvatore Ferragamo - Dufur Ankle Boot
Salvatore Ferragamo Dufur Ankle Boot $660.00
LUXURY
Jeffery-West - Rochester Deadwood
Jeffery-West Rochester Deadwood $650.00
LUXURY

Jeffery-West - Lugosi De Ville
Jeffery-West Lugosi De Ville $575.00
LUXURY
Jeffery-West - Moon Shark Hammerhead Shade
Jeffery-West Moon Shark Hammerhead Shade $563.00
LUXURY
View More Like This Salvatore Ferragamo - Gustavo Boot
Salvatore Ferragamo Gustavo Boot MSRP: $695.00 $555.99
LUXURY
View More Like This Bally - Vilamr Desert Boot
Bally Vilamr Desert Boot MSRP: $595.00 $535.99
LUXURY

View More Like This Salvatore Ferragamo - Dufur Ankle Boot
Salvatore Ferragamo Dufur Ankle Boot MSRP: $660.00 $527.99
LUXURY
View More Like This rag & bone - Spencer Chukka
rag & bone Spencer Chukka $495.00
LUXURY
View More Like This rag & bone - Spencer Chukka
rag & bone Spencer Chukka $495.00
LUXURY
View More Like This eleventy - Double Monk Boot
eleventy Double Monk Boot $495.00
LUXURY

View More Like This Giorgio Armani - Suede Boot
Giorgio Armani Suede Boot MSRP: $625.00 $487.50
LUXURY
View More Like This Salvatore Ferragamo - Gustavo Boot
Salvatore Ferragamo Gustavo Boot MSRP: $695.00 $485.99
LUXURY
View More Like This eleventy - Suede Chukka Boot
eleventy Suede Chukka Boot $475.00
LUXURY
View More Like This Salvatore Ferragamo - Falco Boot
Salvatore Ferragamo Falco Boot MSRP: $580.00 $464.99
LUXURY

Magnanni - Octavian
Magnanni Octavian $450.00
View More Like This Marsell - Gomme Captoe Mid Top
Marsell Gomme Captoe Mid Top MSRP: $660.00 $448.80
LUXURY
View More Like This Magnanni - Valerio
Magnanni Valerio $445.00 Rated: 3 stars!
NEW!
View More Like This Magnanni - Phoenix
Magnanni Phoenix $435.00 Rated: 5 stars!

Mezlan - Dalias
Mezlan Dalias $425.00
View More Like This Salvatore Ferragamo - Falco Boot
Salvatore Ferragamo Falco Boot MSRP: $580.00 $405.99
LUXURY
See by Chloe - SB29161
See by Chloe SB29161 $395.00
LUXURY
Aquatalia - Valeriee
Aquatalia Valeriee $395.00

Aquatalia - Valeriee
Aquatalia Valeriee $395.00
Mezlan - Cabra
Mezlan Cabra $395.00
Mezlan - Cabra
Mezlan Cabra $395.00
View More Like This Vince - Alberto
Vince Alberto $395.00
LUXURY

View More Like This Aquatalia - Raphael
Aquatalia Raphael $395.00
View More Like This eleventy - Slip-On Chukka Sneaker
eleventy Slip-On Chukka Sneaker $395.00
LUXURY
View More Like This Mephisto - Gerald
Mephisto Gerald $389.00
View More Like This Giorgio Armani - Microhole Chukka Boot
Giorgio Armani Microhole Chukka Boot MSRP: $575.00 $379.50
LUXURY

View More Like This Frye - Weston Chukka
Frye Weston Chukka $378.00 Rated: 4 stars!
View More Like This Frye - Weston Chukka
Frye Weston Chukka $378.00 Rated: 4 stars!
View More Like This Frye - Weston Chukka
Frye Weston Chukka $378.00 Rated: 4 stars!
View More Like This Frye - Weston Chukka
Frye Weston Chukka $378.00 Rated: 4 stars!

View More Like This Frye - Weston Chukka
Frye Weston Chukka $378.00 Rated: 4 stars!
View More Like This Frye - Walter Chukka
Frye Walter Chukka $377.95 Rated: 5 stars!
View More Like This Frye - Walter Chukka
Frye Walter Chukka $377.95 Rated: 5 stars!
View More Like This Frye - Walter Chukka
Frye Walter Chukka $377.95 Rated: 5 stars!

View More Like This HELM Boots - Pete
HELM Boots Pete $375.00
View More Like This HELM Boots - Pete
HELM Boots Pete $375.00
View More Like This Jeffery-West - 4 Buckle Chukka
Jeffery-West 4 Buckle Chukka $363.00
LUXURY
View More Like This To Boot New York - Phipps
To Boot New York Phipps $350.00

View More Like This To Boot New York - Franklin
To Boot New York Franklin $350.00
View More Like This Magnanni - Gavin
Magnanni Gavin $350.00 Rated: 5 stars!
View More Like This Vince - Boulder
Vince Boulder $350.00
LUXURY
View More Like This Del Toro - High Top Chukka Sneaker
Del Toro High Top Chukka Sneaker $350.00
LUXURY

View More Like This Mephisto - Claudio
Mephisto Claudio $349.00
View More Like This Mephisto - Claudio
Mephisto Claudio $349.00
View More Like This Robert Clergerie - Beezeena Boot
Robert Clergerie Beezeena Boot MSRP: $575.00 $345.00
LUXURY
BOSS Hugo Boss - Defend Buffalo Leather Desert Boot by HUGO
BOSS Hugo Boss Defend Buffalo Leather Desert Boot by HUGO $345.00

BOSS Hugo Boss - Defend Buffalo Leather Desert Boot by HUGO
BOSS Hugo Boss Defend Buffalo Leather Desert Boot by HUGO $345.00
View More Like This Jeffery-West - 4 Buckle Chukka
Jeffery-West 4 Buckle Chukka $340.00
LUXURY
View More Like This Jeffery-West - 4 Buckle Chukka
Jeffery-West 4 Buckle Chukka $340.00
LUXURY
View More Like This Del Toro - High Top Chukka Sneaker
Del Toro High Top Chukka Sneaker $340.00
LUXURY

View More Like This Del Toro - High Top Chukka Sneaker
Del Toro High Top Chukka Sneaker $340.00
LUXURY
View More Like This Del Toro - High Top Chukka Sneaker
Del Toro High Top Chukka Sneaker $340.00
LUXURY
View More Like This Aquatalia - Carlos
Aquatalia Carlos MSRP: $450.00 $337.50
View More Like This Aquatalia - Carlos
Aquatalia Carlos MSRP: $450.00 $337.50

View More Like This Donald J Pliner - Giacomo-5X
Donald J Pliner Giacomo-5X MSRP: $495.00 $336.60
View More Like This Finn Comfort - Linz - 1008
Finn Comfort Linz - 1008 $335.00 Rated: 5 stars!
View More Like This Frye - Will Chukka
Frye Will Chukka $328.00 Rated: 5 stars!
View More Like This Frye - Will Chukka
Frye Will Chukka $328.00 Rated: 5 stars!

View More Like This Frye - Will Chukka
Frye Will Chukka $328.00 Rated: 5 stars!
View More Like This Vince - Scott
Vince Scott $325.00 Rated: 5 stars!
LUXURY
Mezlan - Castillo
Mezlan Castillo $325.00
View More Like This Vince - Scott
Vince Scott $325.00 Rated: 5 stars!
LUXURY

View More Like This Del Toro - High Top Chukka Sneaker
Del Toro High Top Chukka Sneaker $325.00
LUXURY
View More Like This Toga Virilis - Embossed Leather Western Buckle Boot
Toga Virilis Embossed Leather Western Buckle Boot MSRP: $460.00 $322.99
View More Like This Danner - Tramline
Danner Tramline $320.00 Rated: 4 stars!
View More Like This Frye - Greyson Chukka
Frye Greyson Chukka MSRP: $398.00 $319.99 Rated: 5 stars!

View More Like This Mephisto - Darwin
Mephisto Darwin $319.00
View More Like This Z Zegna - Chukka Boot
Z Zegna Chukka Boot MSRP: $395.00 $315.99
LUXURY
View More Like This Marsell - Gomma Pull-On Chukka
Marsell Gomma Pull-On Chukka MSRP: $630.00 $315.00
LUXURY
View More Like This To Boot New York - Norwalk
To Boot New York Norwalk MSRP: $398.00 $310.44

View More Like This Marsell - Gomme Suede Ankle Boot
Marsell Gomme Suede Ankle Boot MSRP: $620.00 $310.00
LUXURY
View More Like This Timberland - Timberland Boot Company Lucille Lace Chukka
Timberland Timberland Boot Company Lucille Lace Chukka $300.00
View More Like This Timberland - Timberland Boot Company Lucille Lace Chukka
Timberland Timberland Boot Company Lucille Lace Chukka $300.00
Matt Bernson - Andes
Matt Bernson Andes $300.00
NEW!

Cole Haan - Grandevolution Chukka
Cole Haan Grandevolution Chukka $300.00
View More Like This Wolverine - Harwell Chukka
Wolverine Harwell Chukka $300.00
View More Like This Wolverine - Harwell Chukka
Wolverine Harwell Chukka $300.00
Cole Haan - Grand Evolution Chukka
Cole Haan Grand Evolution Chukka $300.00
NEW!

View More Like This Timberland - Boot Company Bardstown Plain Toe Chukka
Timberland Boot Company Bardstown Plain Toe Chukka $300.00
View More Like This Timberland - Boot Company Bardstown Plain Toe Chukka
Timberland Boot Company Bardstown Plain Toe Chukka $300.00
View More Like This Timberland - Boot Company Bardstown Plain Toe Chukka
Timberland Boot Company Bardstown Plain Toe Chukka $300.00
View More Like This Donald J Pliner - Giacomo-5X
Donald J Pliner Giacomo-5X MSRP: $495.00 $297.00

Two24 by Ariat - Prescott
Two24 by Ariat Prescott $295.00
Two24 by Ariat - Prescott
Two24 by Ariat Prescott $295.00
Bacco Bucci - Gerard
Bacco Bucci Gerard $295.00
Bacco Bucci - Gerard II
Bacco Bucci Gerard II $295.00

View More Like This Trask - Gulch 2.0
Trask Gulch 2.0 $295.00 Rated: 5 stars!
View More Like This Jeffery-West - Monk Chukka
Jeffery-West Monk Chukka $295.00
LUXURY
View More Like This Ted Baker - Baise 2
Ted Baker Baise 2 $290.00
View More Like This BUGATCHI - San Gimignano Boot
BUGATCHI San Gimignano Boot $285.00

BUGATCHI - Garda Boot
BUGATCHI Garda Boot $285.00
View More Like This BUGATCHI - San Gimignano Boot
BUGATCHI San Gimignano Boot $285.00
View More Like This Frye - Greyson Chukka
Frye Greyson Chukka MSRP: $398.00 $279.99 Rated: 5 stars!
View More Like This Frye - Greyson Chukka
Frye Greyson Chukka MSRP: $398.00 $279.99 Rated: 5 stars!

Thank You for Registering!

Now, don't miss out on the good stuff...