This interesting surname, with variant spellings Dolles, Dolls etc., has two distinct possible origins. The first, and most likely derivation is from the old English pre 7th Century "dal", (Medieval English "dole"), meaning a "portion or share of land", especially in the common field. The term "dole" was also used of a boundary-mark, and the surname from this source is therefore either topographical from residence by such an area of land, or locational from any of the places named with the above element, such as Dole in Sussex or Doles Ash, in Dorset. The final "s" attached to the surname preserves the old English genitive ending i.e., "of the dole". Doles may also be a patronymic form of the old English personal byname "Dol", (Medieval English "dolle"), meaning "unwise". One, Lewingus Dol was noted in the Domesday Book of 1086, and a Letitia Dolle appears in the 1279 "Hundred Rolls of Cambridgeshire". On April 23rd 1634 Mary Doles and Robert Davis were married in St. Giles, Cripplegate, London. The first recorded spelling of the family name is shown to be that of William de la Dole, which was dated 1273, "The Hundred Rolls of Cambridgeshire", during the reign of King Edward 1st, "The Hammer of the Scots", 1272 - 1307. Surnames became necessary when governments introduced personal taxation. In England this was known as 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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