The first reference that I can find for a Boles in London is in a lease document from 1268 for land with houses "in the parish of St. Edmund, London towards Garcherche, by the grant of Gilbert de Selford, the entry whereof is between the houses of Henry le Paumer and Henry called le Bole."  ref. 

London in 1300, click on the map for a larger image

A grant from 1284 was witnessed by the Mayor, the Sheriffs and an Alderman of London and six individuals including Henry le Bole.  In the grant a mansion was made available to five merchants of  Florence. ref.   A second grant dated 1287 was witnessed by Henry Bole  ref.   and a third grant from 1293 involving a house in St. Michael Cornhill parish was witnessed by Dominus Ralph of Sandwich, Warden of London; Henry le Bole and Elias Russel, Sheriffs of London and some others.  ref.  Henry held the post of one of two Sheriffs of London for the year 1292 to 1293.  ref.   Following his year as Sheriff, Henry was elected as the Alderman for the Bishopsgate Ward in London, held that position from 1293 to 1298 and died in 1301. ref.  ref.  Read further details

I'm not certain of the origins of Henry Bole but I believe it likely that he had come to London from Kent.  The King nominated the head official for the City of London, the Warden, who in turn recommended two Sheriffs every year to be elected for a one year term by the leading citizens of London.  Henry le Bole and Elias Russell were put forward for the Sheriff positions while the Warden was Dominus Ralph of Sandwich, co. Kent.  His two 'pledges' for the election were John de Canterbury and Geoffrey de Hundesdich.  The first was from Kent and the Hundesdich were tanners which was the family occupation of the ‘le Bole’ at Chartham in that period.  The pledges for Elias Russell were made by Henry le Bole and by Walter de Rokesle of Lullingstone, Kent.  Also, there was a Henry Bolle listed in the 1274 Hundred Roll for Canterbury and despite the extensive documents maintained by the Canterbury Cathedral there are no further references for him in Kent after 1274.  I also checked for references to Henry Boles in other parts of England and found many others but they did not fit the timeframe or were still on record in their home counties after Henry appeared in London.  Also, Ivo Boles of Kent held a lease on land near Ickham, Kent in 1259 on land in the demesne of Knoldane held by Reginald de Cornhell (Cornhill).  Most of the Boles in London in the late 1200's lived in the Cornhill ward.  All these connections make a pretty convincing case, some better than others, but there is no absolute proof that Henry was from Kent. 

Another Bole contemporary of Henry's in London was Gilbert le Bole,cordwainer (i.e. a maker of high quality shoes) who used a bull symbol for his seal on his Will.  That discovery is a major argument for at least one branch of the Bowles family having Saxon origins.  See Middle English Origins of the Bowles Name

There are several references to Gilbert le Bole and his son Simon from that period in the Records of the Bridge House Estates held at the Corporation of London Records Office.  The Bridge House Estates were established by Royal Charter in 1282 to maintain and manage the London Bridge which at that time was lined with multi-story buildings, shops and dwellings as well as other nearby properties it acquired as investments.  From the Estate records we find that in 1296 Gilbert le Bole received a grant and quitclaim for a property (tenement) in St. Michael’s parish (in Cornhill ward).  ref.  By his Will of 1304/05 he left his wife Agnes his tenements in St. Michael’s London.  ref.  Two conventions from Simon called le Bole son of the late Gilbert le Bole dated 1324 again provided for his mother Agnes by giving her occupancy in a tenement in the parish of St. Michael le Quern.  ref.  ref.  Simon’s oval seal on the document again shows the device of a bull.  A 1327 grant refers to Simon le Bole, cordwainer, granting “the tenement with houses, in the parish of St. Michael ad Quern” to Simon atte Gate, butcher, and Agnes his wife.  ref.  ref.  Likely, Agnes has remarried and Simon is granting the occupancy of her houses, which he had retained ownership of, to her new husband.  The location of this property is given in a grant from 1356 which describes “two shops with solars above in Watling Street in All Saints Bread Street. They are situated between the tenements of Walter of Tiffield on the West and of Nicholas Bole, skinner on the East and Watling Street on the South and the tenement of Symon atte Gate on North.”  ref. 

Simon le Bole died shortly after.  His father-in-law, Simon atte Gate, contested Simon’s wife Maria’s right to his property due to an adultery which she had committed eight and a half years earlier.  Although Maria argued that she had reconciled with Simon before his death, she did not win her case.  

This may be an indication of a connection to Kent as there were ‘atte Gates’ in Kent including one who signed as a witness on the 1349 grant which mentions the ‘Bolengieresmelle’ mill in the Westgate area outside Canterbury.  I haven’t discovered any proof of such a connection though.

On Dec. 6, 1348 Nicholas Bole, skinner, and Katherine his wife, widow of Simon de Pulham, skinner, came before the Mayor and Aldermen of London and acknowledged that he had the guardianship of Johanna, the daughter of Simon and Katherine, and that he held her property in trust.  Sureties being given by John Bole, skinner, and John de Bedeford, skinner.  ref. 

Unfortunately most of what we know about people’s lives in that period can be learned only from the surviving court documents stored in the London archives.  At that time the churches did not keep parish registers for births, marriages or deaths and there was no civil registration.  It’s unfair to judge these lives only be their court records but it’s all that we have to go by.

In 1304 nine men including John le Bole, tailor and John le Bole, cordwainer were brought before the Mayor, Sheriff and Aldermen of London charged with fighting among themselves in the Chepe of London, committing assault and disturbing the King’s peace.  They were found guilty and were committed to prison until such a time as the Sheriff should be told to release them. The Chepe was the market area in London which both Friday Street and Bread Street ran into.

In 1305 a John, son of Henry le Bole, was arrested for warning John de Romeneye that the Sheriff of London was coming to his house to arrest a certain man there.  ref.

In 1321 William le Bole, a baker on Bread Street, the next street beside Friday Street, was brought before the Mayor and Aldermen of London for producing an underweight bread.  He was found guilty and also guilty for lying in court and was therefore sentenced to be drawn through the city on the hurdle.

A lease from 1342 refers to a tenement  "which the grantor had of John le Bole in the parish of St. Peter de Cornhull."  ref. 

In 1344 a panel of 12 expert skinners in London, including a John Bole, were appointed to investigate charges that members of their profession were not following the regulations laid down for their trade.  ref. 

A grant from 1358 for property adjacent to St. Mary-le-Bow churchyard mentions that it bordered on the tenement of Nicholas Bole in Bread Street to the west and south.  ref. 

In 1384 Robert Litle, citizen and fish monger granted “2 shops in Broad Street in St Bartholomew the Less parish, London, lying with Robert Litle’s shop” to Thomas Bole, ironmonger and citizen of London, and his wife Alice for a term of 24 years.  ref.   Litle would have been holding that property under the ownership of the church though as a document from 1392 lists Thomas Bole, ironmonger's rent at 1s 8d and payable to the Church of Holy Trinity.  ref. 

In 1388 Richard Bole, a butcher, for insulting William Wotton, alderman of  Dowgate, was, by order of the Mayor, imprisoned in Newgate, and ordered, as a penance, to carry a lighted torch, with head uncovered and  bare legs and feet, from his stall in St. Nicholas' Shambles to the Chapel of the Guildhall.  ref.

There is also a grant from 1395 in the Bridge House estate files for a Thomas Bole of Westgrenewiche (now Deptford in Kent).  It involves a shop with a solar and garden (yard) there.  ref. 

Newcourt's Repertorium Volume 1 states that King Richard II founded a perpetual chantry at the altar of St. Katharine at St. Antholin's church  ref.  for the soul of Nicholas Bole.  There is also a petition to King Richard dated Sept. 26, 1397 by several citizens of London to name Thomas Bromley to be the chaplain of the chantry chapel dedicated to the late Nicholas Bole, skinner of London.  ref.  I think it more likely that Nicholas founded the chantry with a bequest from his Will but the reference that it was founded by the King is definitely intriguing and requires further research which might through additional light on the role the Bole's played in London.

John Bolle who was born in Chartham, Kent in about 1400 was a grocer in London, a rather wealthy one based on the house he lived in on Great Tower Street and also the lands which he left to his family in his Will.  From the Will we also know that his wife's name was Blanche, that he had a half-brother William, brothers Richard, Thomas and Henry and a sister Alice.  See John Bolle, Merchant of London

William Bole was apparently the clerk to the Mayor of London in 1401 ref. 

On Feb. 6, 1492/93 a Nicholas Bolle of London subscribed to the oath of the Company of Scriveners of the City of London.  ref. 

For more recent Bowles in London history, please see The Bowles of London and Middlesex.