Chesshyre served for more than forty years as an officer of arms in ordinary to Queen Elizabeth II and as a member of Her Majesty's Household.

Chesshyre undertook heraldic and genealogical work for high-profile clients such as the former prime minister Sir Edward Heath.

In October 2015, a jury sitting at Snaresbrook Crown Court found by a unanimous verdict that Chesshyre had committed child sexual abuse offences in the 1990s.

[12] Having received his Diploma in Education from Oxford, Chesshyre did not enter the teaching profession, but instead was appointed in 1967 to a position as an assistant at the College of Arms.

[24] Following the 1992 Windsor Castle fire Chesshyre was, together with Peter Begent, appointed heraldic consultant for the reconstruction of St George's Hall.

He was also heraldic advisor for the west window of the Henry VII Lady Chapel, donated by John Templeton and devised by Donald Buttress, which The Queen unveiled in 1995.

[35][36] Chesshyre served as heraldic advisor to the committee that organised the re-enactment of the funeral of Arthur, Prince of Wales in Worcester on 3 May 2002.

Chesshyre later successfully lobbied the chief revise editor of The Times to include an explanation of the precise meaning of the term crest in a new edition of the newspaper's staff manual.

[12] The Most Noble Order of the Garter, which Chesshyre co-authored with Peter Begent and Lisa Jefferson, included a foreword by Prince Philip, Duke of Edinburgh.

[41] Another reviewer, Maurice Keen, wrote that it was "invaluable to scholars whose interests touch on the history of the order, from the widest variety of points of view and period specialisation", and that "Altogether, Peter Begent and Hubert Chesshyre have put together a volume that for its thoroughness, its interest and its physical attraction is a worthy tribute to the longevity of England's highest order of chivalry.

"[42] M. K. Ridgway, reviewing The Identification of Coats of Arms on British Silver, wrote that Chesshyre "has the undoubted gift of making a difficult and complicated subject both exciting and interesting".

Four years after he had purchased the property, Saunders contacted Chesshyre with a commission to write a history of Bethnal Green, with particular reference to the legend of the Blind Beggar.

[53] However, after his sexual offences and the forfeiture of his main honour came to light, The Observer reported that the "trustees promptly removed him as vice-president".

[57] In 1998 the Cambridge University Heraldic and Genealogical Society appointed Chesshyre to deliver its annual Mountbatten Memorial Lecture.

[58] Two years later, Chesshyre was a guest of honour at the CUHAGS Fiftieth Annual Dinner held in the Great Hall of Clare College on 25 March 2000.

[59][60] Chesshyre was charged with offences of child sexual abuse and in October 2015 stood trial before a jury sitting at Snaresbrook Crown Court.

"[62] In response to calls by a number of its fellows, the Council of the Society of Antiquaries of London subsequently proposed a resolution to revoke Chesshyre's Fellowship.