The following account is supplied in order to document the various attempts which have been made to document the Bowles of Kent.  This particular account has been since discredited by more recent authorities who now believe that Thomas at the head of the Chislehurst tree was actually John Bolle of Gosberton's second son, Thomas.  See The Bolles of Gosberton

W.H. Bowles writes:

 That there was a family of our name settled in Kent from very early times, and possessed of estates in the neighbourhood of Canterbury, is shown by numerous references in county records. The earliest known settlement of this family was in Shalmesford Street, a hamlet in the parish of Chartham, about three miles from Canterbury. The family house is described in the ancient charters as “Bolles Hall, a Mansion,” which gave its name to a manor of which the Bolles’ were lords. They also had possessions at Chilham and the adjoining parishes, in the city of Canterbury, and at Feversham, and elsewhere in Kent. The first of this line whom I have identified with certainty, and who was probably its founder, was resident in Chartham late in the fourteenth or early in the fifteenth century. This Bolles had by two wives (names unknown) four sons, namely John, Richard, Thomas and William, of which John eventually succeeded to the estates. John was engaged in trade as a “Grocer” (ie. a Levant or Turkey merchant) in London, of which city he was a citizen, with a residence in the parish of All Hallows, Barking (probably in Great Tower Street or Mark Lane, a district which to this day is the chosen haunt of the magnates of our Eastern trade), and was evidently a man of wealth. He married Blanche, herself a Bolles by birth, and twice a widow, having married first a Metford, and next a Castell, thus reverting on her third marriage to her maiden name. Of this marriage there was a son John, who appears to have succeeded his father in the Kentish estates. These are described in the elder John’s will as “the grete place in Shalmesford” and “lands in Chartham,  Chilham, Canterbury and Feversham, all in Kent.” He died in 1461, when his wife removed to Feversham, where probably she had a dower house by settlement, on her husband’s estate, besides the house in London. Blanche died in 1493, leaving a will which was proved in the Prerogative Court of Canterbury.

I regret I cannot throw further light on this early Kentish settlement - a period on which the evidence is scanty and the local registers defective. I think it likely that the Levant business was first established by the original emigrant from Lincolnshire - perhaps the John first mentioned, or his father - and that he settled his country residence within easy reach of London for the convenience of his business, which would then be handed down from father to son along with the family acres. It was quite a common thing in those days for the younger sons of country gentlemen to be placed in trade, which was not then thought in any way to be beyond the pale of class limits. It would indeed have been difficult otherwise to have found careers for young men of family who were not fitted by temperament and training for the learned professions, or endowed with influential connections. There was no standing army or navy; the public service was essentially a closed corporation, available only to the chosen few; the Church as a profession was a thing apart. There remained for the great majority of younger sons only trade, nor was there much distinction drawn between wholesale and retail business. It would be interesting to trace the rise and growth of the singular prejudice so prevalent in the late Georgian and Victorian era, which tainted all commerce with a plebeian aroma. No such notions existed in the day when the first Kentish Bolles was sent by his family to London to make for himself the place in life which the paternal estate could not offer. No doubt the wealth amassed in the city was the purchasing power of the Canterbury estates, and led originally to the settlement in Shalmesford Street of this branch of the old Swineshead stock, who called their new home Bolles Hall, after the ancestral mansion at Swineshead. The course of succession to the Canterbury estates I am unable to trace. It came to an end in the reign of Elizabeth, when the Bolles of the day sold them to one Cracknail and removed altogether from the Canterbury neighbourhood. About the same time, one Thomas Bowle came from the Canterbury neighbourhood and settled himself in the western division of the county, probably at Bromley or Brasted, where his two sons William and John are found during the latter half of the sixteenth century. Whether this Thomas was, as seems most probable, the last inheritor, and the actual vendor of the Canterbury estates, I cannot say, but there can be no reasonable doubt that he was one of the Shalmesford Street family, and that the Bromley and Chislehurst family, which descends from him, can authoritatively claim descent through the Canterbury branch from Lincolnshire.

In writing thus I have not overlooked the fact that Thomas is stated in the visitation [of Heralds] of 1619 to have been “born in the county of Lincoln.” But this is not necessarily inconsistent, rather the reverse. Statements of origin made by the responsible head of the family to the visiting herald were frequently accepted without further evidence being required, and largely depended for their value upon the memory or accuracy of the narrator. In this case, fully a century had elapsed between the removal from Canterbury and the visitation. The record was doubtless made on the narration of Robert Bowle of Chislehurst, who speaks to the original birthplace of his ancestor from tradition only. This, although seldom baseless, is notoriously vague. Robert would know that Thomas (his grandfather) had resided “at or near Canterbury,” and that the family had originally come from Lincolnshire. He may have supposed that Thomas himself had come from Lincolnshire, or he may have stated in general terms that his ancestors had done so. The record based on this narration, whatever it was, though not verbally exact, was probably as correct as those statements often were, and more cannot be looked for. The want of strict verbal accuracy in such records, even in more important matters than a general statement such as this was, is well known to genealogical students. The record may, however, be accepted as evidence that the family were originally from Lincolnshire, which, indeed, is assumed by all writers of authority.