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The term Cavalier () was first used by as a term of abuse for the wealthier royalist supporters of Charles I of England and his son Charles II during the English Civil War, the Interregnum, and the Restoration (1642 – ). It was later adopted by the Royalists themselves. Although it referred originally to political and social attitudes and behaviour, of which clothing was a very small part, it has subsequently become strongly identified with the fashionable clothing of the court at the time. Prince Rupert, commander of much of Charles I's cavalry, is often considered to be an archetypal Cavalier.
Charles, in the Answer to the Petition 13 June 1642, speaks of Cavaliers as a "word by what mistake soever it seemes much in disfavour". It was soon reappropriated as a title of honour by the king's party, who in return applied Roundhead to their opponents. At the Restoration, the court party preserved the name, which survived until the rise of the term Tory.
Most Parliamentarian generals wore their hair at much the same length as their Royalist counterparts,Ashelford, 73 though Oliver Cromwell was something of an exception. The best patrons in the nobility of Charles I's court painter Sir Anthony van Dyck, the archetypal recorder of the Cavalier image, all took the Parliamentary side in the Civil War. Probably the most famous image identified as of a "cavalier", Frans Hals' Laughing Cavalier, shows a gentleman from the strongly Calvinist Dutch town of Haarlem, and is dated 1624. These derogatory terms (for at the time they were so intended) also showed what the typical Parliamentarian thought of the Royalist side – capricious men who cared more for vanity than the nation at large.
The chaplain to King Charles I, Edward Simmons described a Cavalier as "a Child of Honour, a Gentleman well borne and bred, that loves his king for conscience sake, of a clearer countenance, and bolder look than other men, because of a more loyal Heart". There were many men in the Royalist armies who fit this description since most of the Royalist field officers were typically in their early thirties, married with rural estates which had to be managed. Although they did not share the same outlook on how to worship God as the English Independents of the New Model Army, God was often central to their lives. This type of Cavalier was personified by Jacob Astley, 1st Baron Astley of Reading, whose prayer at the start of the Battle of Edgehill has become famous "O Lord, Thou knowest how busy I must be this day. If I forget Thee, do not forget me".
At the end of the First Civil War, Astley gave his word that he would not take up arms again against Parliament and having given his word he felt duty bound to refuse to help the Royalist cause in the Second Civil War; however, the word was coined by the Roundheads as a pejorative propaganda image of a licentious, hard drinking and frivolous man, who rarely, if ever, thought of God. It is this image which has survived and many Royalists, for example Henry Wilmot, 1st Earl of Rochester, fitted this description to a tee. Of another Cavalier, George Goring, Lord Goring, a general in the Royalist army, the principal advisor to Charles II, Edward Hyde, 1st Earl of Clarendon, said:
This sense has developed into the modern English use of "cavalier" to describe a recklessly nonchalant attitude, although still with a suggestion of stylishness. Cavalier remained in use as a description for members of the party that supported the monarchy up until the Exclusion Crisis of 1678–1681 when the term was superseded by "Tory" which was another term initially with pejorative connotations. Likewise, during the Exclusion Bill crisis, the term Roundhead was replaced with "Whig", a term introduced by the opponents of the Whigs and also was initially a pejorative term.
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