The Chepstow is a chukka boot manufactured by Crockett & Jones in Northampton, England. The boot features a design with military roots and is produced with Goodyear welted construction, incorporating waterproof membrane interlining for outdoor use. Multiple versions of the Chepstow are available, including the Chepstow 2 and Chepstow 3, which differ in their last construction and sole specifications.
The boot is characterized by its shortened boot height, elongated vamp, and full leather lining combined with a waterproof membrane. The Chepstow is offered in various leather and suede materials, with different sole options including cleated rubber and Vibram Carrarmato lug soles designed for all-terrain capability.
The Chepstow is manufactured in Northampton, England using Goodyear welted construction. Each pair involves over 200 highly skilled operations during the manufacturing process. The boot features a two-piece pattern with an elongated vamp and proportionally balanced quarter at a shortened boot height. A full leather lining is combined with a waterproof membrane interlining, making the boot suitable for outdoor and winter conditions.
The boot features either two or three eyelets depending on the variant, with gunmetal eyelets on the Chepstow 2 and antique brass eyelets on the Chepstow 3. Heavier than usual laces are used across versions, contributing to the boot's outdoor aesthetic. The Chepstow 3 includes a tan leather notched storm welt for additional water resistance.
The Chepstow 2 is constructed on Last 378, which offers a heavy round toe with increased toe depth and generous forepart fitting, combined with a sculpted heel cup. Last 378 has been described as the maker's "most fashionable and contemporary last." The Chepstow 2 is available with a chunky cleated rubber sole designed for high grip, with some versions featuring a Lightweight Cleated sole, a softer variation of the Vibram cleated sole for improved comfort and flexibility.
The Chepstow 2 is offered in multiple materials with varying prices: Teak Oiled Sides at £545, Dark Brown Suede at £515, Mushroom Suede at £495, and Espresso Calf Suede at £575. The boot is available in sizes six through 12.
The Chepstow 3 is constructed on Last 365, designed for outdoor footwear with a sleek rounded toe and accommodative fit in the forefoot, combined with a moderate waist and heel. This version features a Vibram Carrarmato lug sole developed for all-terrain use with a tank-like tread providing flexibility and durability. A Division Road collaboration version in earth green suede is priced at $675 USD.
The Chepstow is offered in Teak Oiled Sides, an oiled Nubuck leather with water-resistant properties suited for winter use. Multiple suede options are available including mushroom, espresso, dark brown, earth green, sand rough-out, and navy rough-out. The Chepstow 3 uses premium calf suede that is aniline dyed, treated for water resistance, and sanded to create the final finish.
Sole options include a chunky cleated rubber sole on the Chepstow 2 for grip on outdoor terrain, a Lightweight Cleated sole for enhanced comfort, a Vibram Carrarmato lug sole on the Chepstow 3 for all-terrain capability, and Dainite rubber as an available option. The boot is designed for hillside terrain and outdoor activities, combining breathability with sturdy construction for winter-appropriate footwear.
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"Crockett & Jones x DR Chepstow 3 Chukka". Division Road, Inc. Retrieved November 24, 2025.