This interesting and unusual surname is of early medieval English origin. Its etymology is uncertain. The famous Victorian researcher Canon Charles Bardsley, in his "Dictionary of English and Welsh Surnames", says that it is from a nickname for one who shailed. This apparently means one who walked crookedly, a cripple. If so this surname is an example of a sizeable group of early European surnames that were gradually created from the habitual use of nicknames. These nicknames were given with reference to occupation, or to characteristics, such as physical peculiarities, policial correctness not being given much credence in ancient times. The modern surname can be found as Shaylor, Shayler and Shailer. Early surviving recordings from the church registers of Greater London include: the christening of Anne, daughter of Jon and Mary Shaylor, on February 10th 1652, at St. Botolph without Aldersgate; and the marriage of Thomas Shaylor and Margaret Butler on October 19th 1758, at St. Clement Danes, Westminster. The first recorded spelling of the family name is shown to be that of Johannes Scayler. This was dated 1379, in the Poll Tax returns of the West Riding of Yorkshire, during the reign of King Richard 11nd, 1377 - 1399. Surnames became necessary when governments introduced personal taxation. In England this was sometimes known as the Poll Tax. Throughout the centuries, surnames in every country have continued to "develop" often leading to astonishing variants of the original spelling.

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