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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.

22 Results

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 $534.00 $171.00

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 $174.00 $110.00

Unit price
per 

1 color, 1 size
  • 8
Sorel Men Explorer Drift Waterproof 100G Tan Suede Winter Boots size 11
Sold out

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

Sorel

Regular price $181.00 $120.00

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 $401.00 $284.00

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 $248.00 $146.00

Unit price
per 

1 color, 1 size
  • 12
Colorado Men Chukka Red Brown leather boots size 13M
79% off

Colorado Men Chukka Red Brown leather boots size 13M

Colorado

Regular price $257.00 $54.00

Unit price
per 

1 color, 1 size
  • 13