This Company existed from the early 15th century, their stewards being named in a Pentice Court roll of 1423-24. As early as 1428, the tailors received a charter from Henry VI confirming their monopoly of tailoring in Chester in return for an annual payment to the County Palatine. Elizabeth I granted them another charter in 1563. The company was apparently wealthy enough to produce a play in the Chester cycle of Mystery Plays on its own; ‘The Ascension of Christ’.
The Company owned a house near the Newgate which was pulled down in 1596. Afterwards, it rented the Phoenix Tower but by 1835, like many other companies, it held its meetings in local inns. In that year, the company had 21 members.