Unfortunatley, I'm sorry to say, it's not always that straightforward.
There appears to be a distinct OWSLEY family, distinct from the Woosley, with pedigree into the 1300s in England. The WOOSLEY family has pedigeree into the 1400's in England and is believed to be an offshoot of the WOLSELEY family, together with such other variant spellings as WILSILI, WOLFSLEIGH, WOSLEY, WOSSLEY, WOOSSLEY, WOSELEY, WOOZLEY (Welsh), etc. There are distinct OWSLEY and WOOSLEY/WOLSELEY coats of arms if you check the web sites on heraldry.
As I understand things, there are separaete WOOLSEY family lineage from England and the Netherlands. The English WOOLSEY appears to be related to the 14th century WULCI. The WOOLSEY and WOOSLEY are often confused (see some of my earlier posts here and posts on the WOOLSEY family pages at rootsweb/ancestry.com), particularly since the names John and Thomas appear in both families in Virginia in the 1700s.
Both Woosley and Owsley have resulted in offshoots into the OUSLEY, OOSLEY, and OSLEY spellings. On the Woosley side, I know that -- even to this day and among the Kentucky descendants of Samuel Woosley and Phebe Bailey, who exclusively use the Woosley spelling, that both of the following pronunciations are used: Wooz'-li and Ooz'-Li (silent-W).
Based on my readings, Shadrack Woosley/Ousley/Owsley is believed to be the father of the Ousley's of Kentucky; Shadrack would be a son of Benjamin Woosley/Ousley and grandson of family partiarch Thomas Moses Woosley. The Owsleys of Kentucky appear to be descended from Thomas Owsley III. Respectively, these two gentlemen appear to be the grandsons of distinct late-1600's settlers, Thomas (w/wife Mary Unknown) WOSSLEY/WOOSLEY (both spellings appear in his will, Norfolk 1715) and Thomas (w/wife Ann Harris) OWSLEY.
Thomas Moses Woosley is believed by some to be the son of the John Woosley mentioned in the Thomas Woosley will of 1715. However, there are separate references to a Reverend John WOOLSEY who apparently moved to Virginia from New York in the early 1700s and who had a son named Thomas, and there are no distinct references to John Woosley or Ousley from that period that I've ever run across. (The devastation of Virginia courthouses during the Civil War didn't help.) There are also references who trace Thomas Moses Woosley back to a Richard WOOLSEY of the New York Woolseys; this error has entered the International Genealogical Index through posts with the Church of Latter-Day Saints in Salt Lake.
I don't have any final answers -- and freely admit that the inferences I have reported above are my considered opinion based on a dearth of factual data. If there is any lesson to be taken from this, it is the following: Any Virginia record taken from the period of limited literacy of the 1700's has to be carefully vetted for inclusion in the Woosley, Woolsey, or Owsley families; anything posted online without a concrete citation to an original record must be taken with a grain of salt and cross-referenced extensively.
One of these months I hope to prepare a table which details what I've been able to find about each of these families in the hopes that it will help alleviate some of this confusion.
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