Skip navigation

We're celebrating 125 years! Celebrate with Us

Main content

Home
Men
Shoes
Dress Shoes

Men's Chukka Dress Shoes

Paul Chukka (Men)

Frye Paul Chukka (Men)

Current Price $188

Berto Chukka Boot (Men)

Mephisto Berto Chukka Boot (Men)

Current Price $439

Rucci Plain Toe Chukka Boot

Florsheim Rucci Plain Toe Chukka Boot

Current Price $155

Nicky Chukka (Men)

Robert Barakett Nicky Chukka (Men)

Current Price $298

Richard Chukka Boot (Men)

TO BOOT NEW YORK Richard Chukka Boot (Men)

Current Price $450

Calder Chukka Boot (Men)

Johnston & Murphy Calder Chukka Boot (Men)

Current Price $179

Monaco Plain Toe Chukka Boot (Men)

TO BOOT NEW YORK Monaco Plain Toe Chukka Boot (Men)

Current Price $276.25

Previous Price $425

New Markdown

Padror Derby (Men)

KLEMAN Padror Derby (Men)

Current Price $265

A man examining a striped shirt in front of a rack of clothing.

A man examining a striped shirt in front of a rack of clothing.

Styling, Your Way

Whether you're shopping for an everyday item or a special look for a big event, we'll make finding it fun.

Explore Styling Services Book an Appointment

Padror Derby (Men)

KLEMAN Padror Derby (Men)

Current Price $295

Nelson Chukka (Men)

Robert Barakett Nelson Chukka (Men)

Current Price $298

Anthem Plain Toe Chukka (Men)

Florsheim Anthem Plain Toe Chukka (Men)

Current Price $145

Maurilio Chukka Boot (Men)

Magnanni Maurilio Chukka Boot (Men)

Current Price $550

Varick Leather Chukka Boot (Men)

John Varvatos Varick Leather Chukka Boot (Men)

Current Price $398 to $448

Forge Chukka Boot (Men)

Florsheim Forge Chukka Boot (Men)

Current Price $130

Apron Toe Suede Chukka Boot (Men)

Tod's Apron Toe Suede Chukka Boot (Men)

Current Price $925

Austin Chukka Boot (Men)

Gordon Rush Austin Chukka Boot (Men)

Current Price $290

Maxxy Plain Toe Chukka Boot (Men)

Dune London Maxxy Plain Toe Chukka Boot (Men)

Current Price $117

Previous Price $195

Traveler Chukka Boot (Men)

Florsheim Traveler Chukka Boot (Men)

Current Price $135

Chandler Chukka Boot (Men)

Allen Edmonds Chandler Chukka Boot (Men)

Current Price $525

Wells Chukka Boot (Men)

Milwaukee Boot Company Wells Chukka Boot (Men)

Current Price $265

Apron Toe Suede Chukka Boot (Men)

Tod's Apron Toe Suede Chukka Boot (Men)

Current Price $925

Dixon Chukka Boot (Men)

Blake Mckay Dixon Chukka Boot (Men)

Current Price $175

Torres Chukka Boot (Men)

Gentle Souls Torres Chukka Boot (Men)

Current Price $175

Previous Price $250

New Markdown

Corazon Chukka Boot

CARLOS SANTANA Corazon Chukka Boot

Current Price $179

Ted Derby (Men)

John Lobb Ted Derby (Men)

Current Price $1,850

Peppo Water Resistant Chukka Loafer (Men)

Mephisto Peppo Water Resistant Chukka Loafer (Men)

Current Price $549

Dresletic Suede Chukka Boot (Men) (Exclusive Retailer)

BOSS Dresletic Suede Chukka Boot (Men) (Exclusive Retailer)

Current Price $399

Parker Waterproof Chukka Boot (Men)

Johnston & Murphy Parker Waterproof Chukka Boot (Men)

Current Price $129.99

Previous Price $189

Only a few left

Wallabee Chukka Boot (Men)

Clarks® Originals Wallabee Chukka Boot (Men)

Current Price $150 to $170

Roundhill Grand Waterproof Chukka Boot (Men)

Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)

Current Price $260

Field Chukka Boot (Men)

John Lobb Field Chukka Boot (Men)

Current Price $2,310

Fremont Chukka Boot (Men)

Gordon Rush Fremont Chukka Boot (Men)

Current Price $99.90

Previous Price $265

Paolo Moc Toe Loafer (Men)

Vince Paolo Moc Toe Loafer (Men)

Current Price $192.50

Previous Price $275

Only a few left

Chukka Shoe (Men)

McQueen Chukka Shoe (Men)

Current Price $920

Chukka Shoe (Men)

McQueen Chukka Shoe (Men)

Current Price $890

Chocolate Derby (Men)

Prada Chocolate Derby (Men)

Current Price $1,200

The Chukka Boot (Men)

MORJAS The Chukka Boot (Men)

Current Price $430

Hamilton Wingtip Waterproof Chukka Boot (Men)

Allen Edmonds Hamilton Wingtip Waterproof Chukka Boot (Men)

Current Price $550

Only a few left

Morello Chukka Boot

CARLOS SANTANA Morello Chukka Boot

Current Price $149

Easy Chukka Boot (Men)

Santoni Easy Chukka Boot (Men)

Current Price $750

Only a few left

Clarks® Desert Chukka Boot (Men)

Clarks® Originals Clarks® Desert Chukka Boot (Men)

Current Price $140 to $150

Wylie Chukka Boot (Men)

Donald Pliner Wylie Chukka Boot (Men)

Current Price $260

Only a few left

Wally Classic Slip-On (Men)

Hey Dude Wally Classic Slip-On (Men)

Current Price $69.99 to $79.99

Alder Chukka Boot (Men)

Blake Mckay Alder Chukka Boot (Men)

Current Price $99.90

Previous Price $165

Navi Water Resistant Chukka Boot (Men)

Nordstrom For Good

TOMS Navi Water Resistant Chukka Boot (Men)

Current Price $145

Only a few left

Colton Chukka Boot (Men)

Blake Mckay Colton Chukka Boot (Men)

Current Price $79.90

Previous Price $165

Camron Chukka Boot (Men)

Dune London Camron Chukka Boot (Men)

Current Price $150

Only a few left

Detroit Chukka Boot (Men)

Santoni Detroit Chukka Boot (Men)

Current Price $890 to $930

Oslo Schore Chukka Boot (Men)

Magnanni Oslo Schore Chukka Boot (Men)

Current Price $475

Only a few left

Polacco Gomma Chukka Boot (Men)

Tod's Polacco Gomma Chukka Boot (Men)

Current Price $975

Rainer Algonquon Derby (Men)

John Varvatos Rainer Algonquon Derby (Men)

Current Price $848

Gyllsjö Chukka Boots

Myrqvist Gyllsjö Chukka Boots

Current Price $429

Only a few left

Burnished Chukka Boot (Men)

Alden Burnished Chukka Boot (Men)

Current Price $716

'Harrison' Chukka Boot (Online Only) (Men)

Børn 'Harrison' Chukka Boot (Online Only) (Men)

Current Price $145

'Desert' Boot (Men)

Clarks® Originals 'Desert' Boot (Men)

Current Price $150

Last Chukka Boot (Men)

Alden Last Chukka Boot (Men)

Current Price $730

Ben Chukka Boot (Men)

Bottega Veneta Ben Chukka Boot (Men)

Current Price $1,250

'Harrison' Chukka Boot (Online Only) (Men)

Børn 'Harrison' Chukka Boot (Online Only) (Men)

Current Price $145

Smith Chukka Loafer (Men)

John Lobb Smith Chukka Loafer (Men)

Current Price $1,820

Only a few left

Dixon Chukka Boot (Men)

Blake Mckay Dixon Chukka Boot (Men)

Current Price $175

Only a few left

Wallabee Chukka Boot (Men)

Clarks® Originals Wallabee Chukka Boot (Men)

Current Price $170

Only a few left

Barrie Chukka Boot (Men)

Alden Barrie Chukka Boot (Men)

Current Price $716

Chambeliss Chukka Boot (Men)

Christian Louboutin Chambeliss Chukka Boot (Men)

Current Price $1,090

Winter Gommino Chukka Boot (Men)

Tod's Winter Gommino Chukka Boot (Men)

Current Price $975

Daddy Boston Chukka Boot (Men)

Bottega Veneta Daddy Boston Chukka Boot (Men)

Current Price $1,250

Gender Inclusive Lowell Chukka Boot

Dr. Martens Gender Inclusive Lowell Chukka Boot

Current Price $200

Neumel Era Chukka Boot (Men)

Nordstrom For Good

UGG® Neumel Era Chukka Boot (Men)

Current Price $99.99

Previous Price $159.95

Wallabee Kiltie Chukka Boot (Men)

Clarks® Originals Wallabee Kiltie Chukka Boot (Men)

Current Price $170

Only a few left