This Is Big! Receive up to $700 Off Of $2,500 at Moda Operandi With Promo Code SPRING700. SHOP NOW Women Bags Shoes Beauty Jewelry Men Kids Home Offers Sale Editors' Blog Featured Looks

Chukka Shoes & Boots

2619 Products
Sort

Free Shipping $99+: SHIP99

Leather Chukka Boot Leather Chukka Boot extended-info

Narrow-toe chukka boot Leather Criss-cross detail at sides and back Back pull tab Stacked heel Side buckle closure Man-made outsole Measurements: Heel height 0.75", platform...

Zoom
Bell Get Sale Alert

Free 2-Day Shipping + FR

Grenson Declan Men's Boots Grenson Declan Men's Boots extended-info

Exquisite style and quality are never compromised when you choose Grenson. ; Suede chukka boots. ; Pull-on construction. ; Elastic goring to each side for easy on and off. ;...

Zoom
Bell Get Sale Alert

Vans Chukka Low Vans Chukka Low extended-info

The Workwear Oxford Chukka Low, designed by the Vans skate team and inspired by classics like the Authentic and the Chukka Boot, is made with textile and suede uppers, original...

Zoom
Bell Get Sale Alert

Common Projects Chukka in Tan Suede Common Projects Chukka in Tan Suede extended-info

Classic chukka boot from Common Projects in Tan. Suede upper. Almond toe. Minimalist lace-up front with round cotton laces. Tonal stitching. Subtle heat pressed gold serial...

Zoom
Bell Get Sale Alert

English Laundry Men's Hunt Chukka Boot English Laundry Men's Hunt Chukka Boot extended-info

Captoechukkaboot

Zoom
Bell Get Sale Alert

Superdry Dakar Suede Boot Superdry Dakar Suede Boot extended-info

World renowned with inspiration from both American and Japanese culture; Superdry is a worldwide phenomenon showing no signs of slowing down. This Chukka inspired silhouette...

Zoom
Bell Get Sale Alert

Free Shipping & Returns

Dr. Martens Baynes Chukka Dr. Martens Baynes Chukka extended-info

When the Dr. Martens boot first catapulted from a working-class essential to a counter-cultural icon back in the 1960s, the world was pre-internet, pre-MTV, pre-CD, pre-mp3s,...

Zoom
Bell Get Sale Alert

H Shoes by Hudson Men's Matteo Suede Chukka Boots Navy H Shoes by Hudson Men's Matteo Suede Chukka Boots Navy extended-info

‘Matteo’ suede chukka boots from from contemporary London-based footwear label H Shoes by Hudson. Expertly constructed from smooth suede uppers, the desert boots feature classic...

Zoom
Bell Get Sale Alert

Free Delivery & Returns

Oliver Spencer Baxter Suede Chukka Boots Oliver Spencer Baxter Suede Chukka Boots extended-info

Oliver Spencer has brought back the 'Baxter' Chukka boot for Spring '17 with a "new smarter look" and robust leather soles. This suede pair is finished with the label's...

Zoom
Bell Get Sale Alert

H Shoes by Hudson Men's Matteo Suede Chukka Boots Brown H Shoes by Hudson Men's Matteo Suede Chukka Boots Brown extended-info

‘Matteo’ suede chukka boots from from contemporary London-based footwear label H Shoes by Hudson. Expertly constructed from smooth suede uppers, the desert boots feature classic...

Zoom
Bell Get Sale Alert

Free Delivery & Returns

Yuketen Sports Chukka Textured-Leather Boots Yuketen Sports Chukka Textured-Leather Boots extended-info

Yuketen 's 'Sports Chukka' boots are a heritage style optimised for comfortable everyday wear. They are cut from 'flesh out' leather that has the tactility of suede with even...

Zoom
Bell Get Sale Alert

Stacy Adams Dabney Chukka Boot Stacy Adams Dabney Chukka Boot extended-info

Sizing: True to size. Round toe. Suede construction. Topstitching. Lace-up. Lightly padded insole. Lug sole. Approx. 4 shaft height. Imported

Zoom
Bell Get Sale Alert

Andrew Marc Saxom Chukka Boot Andrew Marc Saxom Chukka Boot extended-info

Sizing: True to size. Round toe. Lace-up vamp. Leather construction. Topstitched detail. Grip sole. Approx. 5.25 shaft height. Imported

Zoom
Bell Get Sale Alert

Free Shipping $100+

Bogs Johnny Chukka Waterproof Boot Bogs Johnny Chukka Waterproof Boot extended-info

Sizing: True to size. Waterproof Round toe Gore insets Lace-up closure Back pull-tab Removable padded insole Welt midsole Grip sole Approx. 4" shaft height ...

Zoom
Bell Get Sale Alert

Free Shipping any 2+ items

Stacy Adams Strickland Plain Toe Lace Chukka Boot Stacy Adams Strickland Plain Toe Lace Chukka Boot extended-info

Keep your dapper appeal for every occasion in these Stacy Adams chukka boots. ; Leather upper with perforated details. ; Lace-up construction. ; Plain toe. ; Leather lining. ;...

Zoom
Bell Get Sale Alert

UGG Men's Freamon Capra Treadlite Leather Chukka Boots Mole UGG Men's Freamon Capra Treadlite Leather Chukka Boots Mole extended-info

Men's leather chukka boots from UGG. Crafted from soft leather with a classic 'chukka' silhouette, the 'Freamon Capra' ankle boots feature an open lacing system with two eyelet...

Zoom
Bell Get Sale Alert

Common Projects Chukka in Black Suede Common Projects Chukka in Black Suede extended-info

Classic chukka boot from Common Projects in Black. Suede upper. Almond toe. Minimalist lace-up front with round cotton laces. Tonal stitching. Subtle heat pressed gold serial...

Zoom
Bell Get Sale Alert

Free 2-Day Shipping + FR

Robert Clergerie Beeze Boot Men's Boots Robert Clergerie Beeze Boot Men's Boots extended-info

Dash around town in the stylish and riveting Beeze Boot from Robert Clergerie. ; Chukka boot design. ; Genuine leather upper. ; Lace-up closure with metal eyelets. ; Slip-on...

Zoom
Bell Get Sale Alert

Free shipping $40+

Shoe the Bear Shoe The Bear Suede Chelsea Boots Shoe the Bear Shoe The Bear Suede Chelsea Boots extended-info

Boots by Shoe The Bear, Soft-touch suede, Pull tab to reverse, Elasticated inserts, Textured sole, Treat with a leather protector, 100% Real Leather uppers. ABOUT SHOE THE BEAR...

Zoom
Bell Get Sale Alert

Free Shipping $99+: SHIP99

John Varvatos Star R Chukka Boot John Varvatos Star R Chukka Boot extended-info

Round-toe chukka boot Leather and textile Lace-up vamp Back pull tab Padded collar Man-made outsole Measurements: Heel height 1", platform sole 1", shaft height 4", calf...

Zoom
Bell Get Sale Alert

Lugz Men's Roamer Hi Chukka Boot Lugz Men's Roamer Hi Chukka Boot extended-info

Themen'sroamerhiisaclassic6inchmoctoebootthatwillworkhardforyouandnevergooutofstyle.constructedwithdurablecomponents,thesebootsfeatureapaddedtongueandcollar,cushionedinsole,bran...

Zoom
Bell Get Sale Alert

Jambu Tavern (Men's) Jambu Tavern (Men's) extended-info

Buttery-soft leather and contrast stitching make this chukka boot any man's go-to choice for rugged style Tumbled nubuck or vintage leather upper with classic lace-up closure ...

Zoom
Bell Get Sale Alert

Free Ship & Free Return

Columbia Sunvent Chukka Columbia Sunvent Chukka extended-info

Spend a weekend on the town in the easy, sophisticated style of the Columbia Sunvent Chukka boot. ; Soft canvas and leather upper materials. ; Lace-up closure. ; Heel pull tab....

Zoom
Bell Get Sale Alert

Free Shipping $75+

Crevo Men's Alameda Chukka Boot Crevo Men's Alameda Chukka Boot extended-info

Rugged yet fashionable, the Alameda Chukka Boot from Crevo.p Suede or leather upper in a casual chukka boot style with a round toe Lace up front Stitching detail Smooth...

Zoom
Bell Get Sale Alert

Extra 20% Off: FEBDEAL

Rocky Men's Cruiser Casual Western Chukka Boot Rocky Men's Cruiser Casual Western Chukka Boot extended-info

From the office to a night out on the town, the Rocky Cruiser Casual Western Chukka Boot is thoughtfully crafted with suede leather and a sturdy rubber outsole. If your everyday...

Zoom
Bell Get Sale Alert

Free Shipping $99+: SHIP99

John Varvatos Mick Crepe Chukka Boot John Varvatos Mick Crepe Chukka Boot extended-info

Roper-toe chukka boot Leather and textile Lace-up vamp Back pull tab Logo patch and appliqués at back Man-made outsole " material="Leather, textile and man-made material"...

Zoom
Bell Get Sale Alert

Free Ship & Free Return

Messico Oliver Messico Oliver extended-info

Messico shoes feature a handmade European last. This allows for the toe region to have more room while offering a snug fit throughout the arch and heel. Circulation and comfort...

Zoom
Bell Get Sale Alert

Timberland Killington Hiker Chukka (Men's) Timberland Killington Hiker Chukka (Men's) extended-info

This cool-looking urban hiker lets you go the extra mile in comfort Nubuck leather upper Lace-up closure Breathable, partially recycled PET mesh lining OrthoLite®...

Zoom
Bell Get Sale Alert

Free Delivery & Returns

Yuketen Sports Chukka Textured-Leather Boots Yuketen Sports Chukka Textured-Leather Boots extended-info

Yuketen looks to relaxed 1960s styles to create these 'Sports Chukka' boots. Set on spongy rubber-crepe soles, they are made from 'flesh out' leather that has an exaggerated...

Zoom
Bell Get Sale Alert

Clarks Men's Broyd Mid Chukka Boot Clarks Men's Broyd Mid Chukka Boot extended-info

Comfortcasual

Zoom
Bell Get Sale Alert

Free Shipping any 2+ items

Florsheim Hamilton Chukka Boot Florsheim Hamilton Chukka Boot extended-info

Keep your work ensemble sharp and dapper in the timeless style of the Florsheim Hamilton chukka boot. ; Smooth leather or suede leather uppers. Depending upon color selected. ;...

Zoom
Bell Get Sale Alert

Free Delivery & Returns

WANT Les Essentiels Edwards Suede Chukka Boots WANT Les Essentiels Edwards Suede Chukka Boots extended-info

WANT LES ESSENTIELS focuses on creating "timeless pieces that place equal value on fashion and function". Detailed with the brand's signature silver studs, these chukka boots...

Zoom
Bell Get Sale Alert

Free Ship & Free Return

Kenneth Cole New York Take Comfort Kenneth Cole New York Take Comfort extended-info

Be the best dressed in your office wearing these Kenneth Cole New York Take Comfort ankle boots. ; Made in Italy. ; Suede leather upper. ; Double-eyelet lace construction on a...

Zoom
Bell Get Sale Alert

Free Shipping & Returns

Deer Stags Men's 'Seattle' Leather Chukka Boot Deer Stags Men's 'Seattle' Leather Chukka Boot extended-info

Lustrous leather elevates a sleek chukka boot shaped in a classic silhouette. Brand: DEER STAGS. Style Name:Deer Stags 'seattle' Leather Chukka Boot (Men). Style Number:...

Zoom
Bell Get Sale Alert

Free Shipping & Returns

Men's Clarks Originals 'Desert' Boot Men's Clarks Originals 'Desert' Boot extended-info

A crepe outsole provides added cushioning and comfort for a vintage-style chukka boot shaped from smooth, supple leather. Brand: Clarks Originals. Style Name:Clarks Originals...

Zoom
Bell Get Sale Alert

Free Shipping & Returns

Stacy Adams Men's 'Madison Ii' Chukka Boot Stacy Adams Men's 'Madison Ii' Chukka Boot extended-info

Clean, classic style defines a versatile chukka boot crafted in a stylish silhouette. Brand: STACY ADAMS. Style Name:Stacy Adams 'Madison Ii' Chukka Boot (Men). Style Number:...

Zoom
Bell Get Sale Alert

Free Shipping $50+

Vans Desert Chukka Leather Honey Boots Vans Desert Chukka Leather Honey Boots extended-info

Elevate your shoe game with help from the Vans Desert Chukka Leather Boots. These rad shoes feature a premium leather upper, a mid profile silhouette, comfortable UltraCush...

Zoom
Bell Get Sale Alert

Free 2-Day Shipping + FR

Giorgio Armani Microhole Chukka Boot Men's Boots Giorgio Armani Microhole Chukka Boot Men's Boots extended-info

Dash around town in the stylish and riveting Microhole Chukka Boot from Giorgio Armani. ; Textured leather upper with perforated detail adorned throughout. ; Lace up closure...

Zoom
Bell Get Sale Alert

Free Shipping any 2+ items

Clarks Trapell Mid Clarks Trapell Mid extended-info

The Trapell Mid is part of the Clarks 1825 Collection. ; An international classic, the Trapell Mid picks up where less distinctive chukka boots leave off. ; Soft, supple suede...

Zoom
Bell Get Sale Alert

Dr. Martens Men's Cruise Cabrillo Suede Chukka Boots Tan Dr. Martens Men's Cruise Cabrillo Suede Chukka Boots Tan extended-info

Men’s ‘Cabrillo’ tan suede desert boots from the Dr. Martens Cruise collection. Crafted from smooth suede, the chukka boots are fastened with a two-eyelet laced closure....

Zoom
Bell Get Sale Alert
Chukka Shoes & Boots - ShopStyle