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Men Chukka Boots

574 items found
574 items

Bruno Magli

Joker

$162.99MSRP: $325.00

John Varvatos

Zander Chukka Boot

$159.99MSRP: $228.00

Frye

Will Chukka

$164.00MSRP: $328.00

Steve Madden

Cove

$80.99MSRP: $125.00

Original Penguin

Myles

$104.99MSRP: $190.00

COACH

Shearling Desert Boot

$177.99MSRP: $295.00

Bruno Magli

Joker

$162.99MSRP: $325.00

Steve Madden

Trevor

$49.99MSRP: $100.00

Lucky Brand

Mason

$43.49MSRP: $125.00

Cole Haan

2.Zerogrand Chukka

$175.99MSRP: $320.00

Original Penguin

Myles

$85.99MSRP: $190.00

Van Heusen

Gibson

$60.99MSRP: $89.99

Florsheim

Pivot Chukka Boot

$85.99MSRP: $110.00

Roan

Atlas

$44.99MSRP: $99.95

Nunn Bush

Galloway Plain Toe Chukka Boot

$39.99MSRP: $80.00

ECCO

Crepetray Chukka Mid

$99.99MSRP: $180.00

Danner

Wolf Creek Chukka

$113.25MSRP: $180.00

Timberland

Cross Mark PT Chukka

$79.99MSRP: $120.00

Van Heusen

Gibson

$60.99MSRP: $89.99

Calvin Klein

Rolando

$67.99MSRP: $150.00

BOSS Hugo Boss

Bohemian Suede Chukka By HUGO

$174.99MSRP: $348.00

Mezlan

Simon

$177.99MSRP: $355.00

Kenneth Cole New York

Dance Chukka

$79.99MSRP: $160.00

Bullboxer

Alta

$86.99MSRP: $130.00

SOREL

Madson Chukka Waterproof

$135.99MSRP: $170.00

ECCO

Newcastle Chukka Boot

$109.99MSRP: $220.00

Birkenstock

Troy

$109.99MSRP: $200.00

Danner

Wolf Creek Chukka

$117.99MSRP: $180.00

Danner

Wolf Creek Chukka

$89.99MSRP: $180.00

SKECHERS

Relaxed Fit Metco Atmore Boot

$44.99MSRP: $75.00

Steve Madden

Kurtis

$64.99MSRP: $100.00

TOMS

Bota

$55.99MSRP: $74.95

Kenneth Cole Reaction

Desert Sun

$44.99MSRP: $98.00

Mezlan

Cavill

$149.99MSRP: $375.00

Kenneth Cole Reaction

Casino Chukka

$65.99MSRP: $110.00

Steve Madden

Lundin

$80.99MSRP: $115.00

ALDO

Messias

$85.99MSRP: $155.00

Sebago

Smyth Chukka

$45.00MSRP: $149.95

Robert Wayne

Minos 2

$47.99MSRP: $100.00

Florsheim

Union Plain Toe Chukka Boot

$77.99MSRP: $110.00

Rockport

DresSports 2 Go Boot

$70.99MSRP: $129.95

Stacy Adams

Dublin II

$47.99MSRP: $85.00

Stacy Adams

Madison II - 65

$54.99MSRP: $180.00

Stacy Adams

Ashby Cap Toe Chukka Boot

$57.99MSRP: $105.00

SOREL

Ace™ Chukka Waterproof

$90.00MSRP: $200.00

Stacy Adams

Ackerly

$42.99MSRP: $104.95

Cole Haan

2.Zerogrand Chukka

$127.99MSRP: $320.00

Frye

Ashland Chukka

$194.99MSRP: $278.00

Stacy Adams

Avery

$59.99MSRP: $100.00

Sperry

Gold Crepe Chukka Suede

$120.99MSRP: $220.00

Timberland

Squall Canyon Wingtip Waterproof Chukka

$119.99MSRP: $150.00

Frye

Weston Chukka

$151.20MSRP: $378.00

TOMS

Bota

$49.99MSRP: $74.95

Frye

Ashland Chukka

$139.99MSRP: $278.00

Sperry

Caspian Chukka

$84.99MSRP: $139.95

Robert Wayne

Minos

$57.99MSRP: $115.00

Robert Wayne

Minos

$57.99MSRP: $115.00

Kenneth Cole Reaction

Desert Sun

$49.99MSRP: $98.00

Calvin Klein

Rueben

$50.00MSRP: $135.00

Calvin Klein

Rueben

$50.00MSRP: $135.00

Woolrich

Yaktak

$70.99MSRP: $130.00

Florsheim

Union Plain Toe Chukka Boot

$77.99MSRP: $110.00

Woolrich

World Traveler

$54.99MSRP: $120.00

Woolrich

Yaktak

$59.99MSRP: $130.00

Woolrich

World Traveler

$59.99MSRP: $120.00

Roan

Stone by Roan

$44.99MSRP: $89.95

Calvin Klein

Rolando

$74.99MSRP: $150.00

Donald J Pliner

Leon

$112.99MSRP: $225.00

Dr. Martens

Holt Revive

$79.99MSRP: $135.00

To Boot New York

Banker

$187.99MSRP: $375.00

Mark Nason

Eastwood

$64.99MSRP: $130.00

Dr. Scholl's

Airborne - Original Collection

$40.99MSRP: $90.00

Bruno Magli

Principe

$165.99MSRP: $475.00

Florsheim

Belfast Plain Toe Size Zip Boot

$87.99MSRP: $134.95

Mezlan

Dalias

$149.99MSRP: $425.00

Stacy Adams

Dublin II

$42.99MSRP: $85.00

Stacy Adams

Wally Moc Toe Chukka Boot Sneaker

$44.99MSRP: $75.00

Florsheim

Union Plain Toe Chukka Boot

$77.99MSRP: $110.00

Cole Haan

Wagner Grand Apron Chukka

$125.99MSRP: $280.00

Trask

Brady

$134.99MSRP: $245.00

Mezlan

Cabra

$157.99MSRP: $395.00

Stacy Adams

Dublin II

$42.99MSRP: $85.00

To Boot New York

Banker

$187.99MSRP: $375.00

Cole Haan

Pinch Rugged Chukka

$99.99MSRP: $180.00

Ben Sherman

Omega Casual Chukka

$57.99MSRP: $110.00

Ben Sherman

Omega Casual Chukka

$57.99MSRP: $110.00

Ben Sherman

Omega Casual Chukka

$64.99MSRP: $110.00

Polo Ralph Lauren

Karlyle

$59.99MSRP: $170.00

Vans

Desert Chukka

$52.99MSRP: $95.00

Polo Ralph Lauren

Karlyle

$51.00MSRP: $170.00

BUGATCHI

Verona Chukka Boot

$117.99MSRP: $335.00

To Boot New York

Alcor

$157.99MSRP: $450.00

SOREL

Ace™ Chukka Waterproof

$90.00MSRP: $200.00

Wolverine Heritage

Cort Waterproof Leather Chukka

$67.99MSRP: $170.00

Caterpillar Casual

Stats

$60.99MSRP: $110.00

Caterpillar Casual

Stats

$54.99MSRP: $110.00

SOREL

Ace™ Chukka Waterproof

$90.00MSRP: $200.00

UGG

Neumel

$69.99MSRP: $139.95

UGG

Maksim

$49.98MSRP: $124.95

UGG

Freamon HyperWeave

$74.98MSRP: $149.95