Kaylee is one of those names that seemingly appeared out of the blue sometime in the 20th century. It seems like each name book you find has a different meaning for it; some saying it's Irish, some Greek, etc. In reality, I think it's probably a combination of Kay and Lee, modeled after such names as Hayley, Keely, Kelly etc. The Irish word Céilí and Scottish Gaelic word Ceilidh may have provided some inspiration as well, both of those signifying a social gathering with music and/or dancing. There exists a fairly rare Irish surname Cayley, which means 'descendent of Caolaidh [a personal name meaning 'slender; fair' and is a man's name]). There is also an English surname coming from the place name Cayley, made up of germanic elements meaning 'jackdaw' and 'forest; clearing; field.' However, I'm not sure all these surnames have anything to do with the modern usage of Kaylee-- I think it's a 20th century invention without any 'real' meaning outside of Kay (usually a derivative of Katherine, whose meaning is obscure) and Leigh/Lee (from an English surname meaning 'field; clearing; forest'). It appeared in the US top 7000 names in 1940 and was used sporadically until it gained popularity in the 1980s. It has been growing in popularity ever since, and if you take into consideration all the variant spellings, it was #11 in the US top 7000 in 2010.
See Also: Caliegh, Caley, Céilí, Kaeli, Kaylea, Kaele, Kaleigh, Kaily, Kayleigh, Kaley

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