He was admitted to the freedom of the
Worshipful Company of Mercers on 17 September 1499 and became
master of the company in 1528. He was elected
Sheriff of London in 1527. He was knighted by
Henry VIII in 1533 and became
Lord Mayor of London on St Edward's Day, 13 October, 1539. On 3 January 1539–40 he received in great state
Anne of Cleves on her way through the city before her marriage On 4 February, Holles and the Aldermen accompanied the king and queen by water to Westminster. Holles was a wealthy merchant, and besides two houses in London, one in
Bishopsgate Street, where he kept his mayoralty, and another in the parish of
St Mary-le-Bow, acquired several manors in Derbyshire, Nottinghamshire, Staffordshire, Middlesex and Essex. He also was the owner of
Clement's Inn in the Strand. ==Death and legacy==