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Men Chukka Boots

Discover our exclusive Designer Men’s Chukka Boots collection, where timeless style meets modern craftsmanship. Perfect for the discerning gentleman, each pair in this curated selection is meticulously crafted from premium materials such as rich leather and supple suede, ensuring both durability and sophisticated appeal. Our Chukka boots feature versatile designs that effortlessly transition from casual outings to more formal occasions, offering unmatched comfort and style. With a variety of colors, finishes, and detailing, you’ll find the perfect pair to complement your wardrobe. Enjoy features like cushioned insoles, durable outsoles, and impeccable stitching that highlight the quality and attention to detail in every boot. Elevate your footwear game with our Designer Chukka Boots, where luxury and versatility meet.

17 Results

Shoe The Bear Men Dev Sand Suede handcraft Office Chelsea boots 9.5-10US EUR43
38% off

Shoe The Bear Men Dev Sand Suede handcraft Office Chelsea boots 9.5-10US EUR43

Shoe The Bear

Regular price $241.00 $149.00

Unit price
per 

1 color, 1 size
  • 9.5-10
Cole Haan Men American Classics Plain Toe Wide Black Leather Combat Boots size 7W
54% off

Cole Haan Men American Classics Plain Toe Wide Black Leather Combat Boots size 7W

Cole Haan

Regular price $277.00 $127.00

Unit price
per 

1 color, 1 size
  • 7W
BOGS Men Spruce Brown Leather Chelsea Slip Boots size 11.5
47% off

BOGS Men Spruce Brown Leather Chelsea Slip Boots size 11.5

BOGS

Regular price $241.00 $127.00

Unit price
per 

1 color, 1 size
  • 11.5
Bruno Magli Men Paris Grey Distressed Leather Chelsea Dress Boots size 9
36% off

Bruno Magli Men Paris Grey Distressed Leather Chelsea Dress Boots size 9

Bruno Magli

Regular price $390.00 $248.00

Unit price
per 

1 color, 1 size
  • 9
Born Men Shane Pull on taupe Suede Chelsea Boots size 12
40% off

Born Men Shane Pull on taupe Suede Chelsea Boots size 12

Born

Regular price $212.00 $127.00

Unit price
per 

1 color, 1 size
  • 12
Antonio Maurizi Wingtip Brown Leather Lace-up Boots size 10.5-11US EUR41
43% off

Antonio Maurizi Wingtip Brown Leather Lace-up Boots size 10.5-11US EUR41

Antonio Maurizi

Regular price $560.00 $319.00

Unit price
per 

1 color, 1 size
  • 10.5-11
Florsheim Men Lodger Brown Leather Low Lace up Boots size 8
54% off

Florsheim Men Lodger Brown Leather Low Lace up Boots size 8

Florsheim

Regular price $277.00 $127.00

Unit price
per 

1 color, 1 size
  • 8
AllSaints Men Jesiah Elastic Panels Brown Leather Chelsea Boots 9US EUR40
37% off

AllSaints Men Jesiah Elastic Panels Brown Leather Chelsea Boots 9US EUR40

AllSaints

Regular price $560.00 $355.00

Unit price
per 

1 color, 1 size
  • 9
Frye Men Peyton Slate Elastic Grain Leather Short Chelsea Boots Size 8.5
Sold out

Frye Men Peyton Slate Elastic Grain Leather Short Chelsea Boots Size 8.5

Frye

Regular price $423.00 $212.00

Unit price
per 

1 color, 1 size
  • 8.5
Saint Laurent Paris Men Wyatt Beige Suede Elastic Chelsea Boots size 13US EUR 46
40% off

Saint Laurent Paris Men Wyatt Beige Suede Elastic Chelsea Boots size 13US EUR 46

Saint Laurent Paris

Regular price $1,630.00 $985.00

Unit price
per 

1 color, 1 size
  • 13
Donald Pliner Men Roccocs Caramel Elastic Gussets Suede Dress Chelsea Boots sz 9
68% off

Donald Pliner Men Roccocs Caramel Elastic Gussets Suede Dress Chelsea Boots sz 9

Donald Pliner

Regular price $546.00 $175.00

Unit price
per 

1 color, 1 size
  • 9
Bogs Men Freedom Faux Fur Lined Waterproof Black Leather Chelsea boots size 8
37% off

Bogs Men Freedom Faux Fur Lined Waterproof Black Leather Chelsea boots size 8

Bogs

Regular price $178.00 $112.00

Unit price
per 

1 color, 1 size
  • 8
AllSaints Men Mathias Navy Blue Suede Lace-up Chukka Boots 12US EUR46
68% off

AllSaints Men Mathias Navy Blue Suede Lace-up Chukka Boots 12US EUR46

AllSaints

Regular price $560.00 $178.00

Unit price
per 

1 color, 1 size
  • 12
Sorel Men Explorer Drift Waterproof 100G Tan Suede Winter Boots size 11
34% off

Sorel Men Explorer Drift Waterproof 100G Tan Suede Winter Boots size 11

Sorel

Regular price $185.00 $122.00

Unit price
per 

1 color, 1 size
  • 11
Good Man Brand Men Edge Lace-Up Grey Fine Suede Ankle Boots Size 13
29% off

Good Man Brand Men Edge Lace-Up Grey Fine Suede Ankle Boots Size 13

Good Man Brand

Regular price $410.00 $291.00

Unit price
per 

1 color, 1 size
  • 13
Johnston & Murphy Men Chukka Dress Brown Leather Boots size 12
41% off

Johnston & Murphy Men Chukka Dress Brown Leather Boots size 12

Johnston & Murphy

Regular price $254.00 $149.00

Unit price
per 

1 color, 1 size
  • 12