Chukka Boots
Men's Brown and Blue Pebbled Leather Chukka Boots — Kirkwood
From $265.00 USD
Men's Brown and Blue Pebbled Leather Chukka Boots — Kirkwood - color variant: Brown
Men's Brown and Blue Pebbled Leather Chukka Boots — Kirkwood - color variant: Black
Men's Brown and Blue Pebbled Leather Chukka Boots — Kirkwood - color variant: Tan
Men's Brown Plain-Toe Leather Chukka Boots — Woolworth
From $265.00 USD
Men's Brown Plain-Toe Leather Chukka Boots — Woolworth - color variant: Brown
Men's Brown Plain-Toe Leather Chukka Boots — Woolworth - color variant: Black
Men's Brown Plain-Toe Leather Chukka Boots — Woolworth - color variant: Tan
Men's Olive Green Plain-Toe Suede Ankle Boots — Headington
From $265.00 USD
Men's Olive Green Plain-Toe Suede Ankle Boots — Headington - color variant: Hunter Green Green
Men's Olive Green Plain-Toe Suede Ankle Boots — Headington - color variant: Black
Men's Olive Green Plain-Toe Suede Ankle Boots — Headington - color variant: Walnut
Men's Brown and Beige Cap-Toe Leather Chukka Boots — Fulton
From $265.00 USD
Men's Brown and Beige Cap-Toe Leather Chukka Boots — Fulton - color variant: Black
Men's Brown and Beige Cap-Toe Leather Chukka Boots — Fulton - color variant: Walnut
Men's Brown and Beige Cap-Toe Leather Chukka Boots — Fulton - color variant: Tan
Chukka boots in this collection are custom made to measure, offering a tailored fit in a range of leathers and finishes. You'll find brown and blue pebbled leather chukkas, plain-toe designs, and dark brown suede options, each cut for a clean ankle-high silhouette and finished with open lacing for easy wear.
The collection includes classic brown plain-toe chukka boots like the Woolworth and Gardner, as well as black and dark brown suede pairs such as the Popham and Harlowe, which provide a softer look and feel. For those seeking extra detail, there are cap-toe and double monk strap chukka boots, including reddish-brown and two-tone styles that add a distinctive edge. Each pair is made to your foot size and width, from narrow to extra-wide, or adjusted to your measurements for a precise fit. If you’re interested in other silhouettes, the Lace Up Boots and Men's Leather Dress Boots collections offer additional options.