Thigh high riding boots were first worn with buff coats by gentlemen and soldiers during the mid-Tudor period. By the reign of Elizabeth I these had low heels to facilitate riding and were made of soft brown leather.
By the reign of James I boots had replaced shoes as the most popular footwear among the upper classes who often wore them indoors, even with spurs. By the 1620s they resembled the boots worn by the Three Musketeers, with a flared bucket-shaped top and high wooden heels similar to those on cowboy boots.
Boots of this type are stereotypically associated with the dashing Cavalier of the English Civil War but in reality many Roundheads, including the Earl of Essex, dressed identically to the Royalists. Cavalier boots remained in use among cavalry until the late 18th century when they were replaced with the Hessian boots popularised by Prussian king Frederick the Great.
Cavalier boots are often associated with pirates and highwaymen like Dick Turpin or Captain Blood. These tall boots were prized by helmsmen and naval officers as they provided excellent protection from rain and spray. Boots of this design, worn with a Sou'wester and oilskins, remained in use among fishermen well into the 20th century when they were replaced with rubber Wellington boots and waders.
Cavalier boots underwent a revival during the American Civil War when flamboyant cavalry officers like George Armstrong Custer and Jeb Stuart purchased thigh-high riding boots. Following the successful Pirates of the Caribbean films boots of this type have also become popular among young British women.
King Charles I wearing Cavalier boots
- Painting of musketeers wearing cavalier boots
- French gentlemen wearing bucket top boots Archived 2011-09-28 at the Wayback Machine
- Cavalier or Roundhead? Archived 2011-07-26 at the Wayback Machine
- IMDB: Captain Blood
- [Wert, Jeffry D. (1996). Custer: The Controversial Life of George Armstrong Custer. New York: Simon & Schuster. ISBN 0-684-81043-3, p. 15.]