These four crafts developed in the early 16th century. The painters were heraldic painters: the glaziers catered for the growing use of glass; the embroiderers embellished materials and the stationers were concerned with bookbinding and book selling. In 1534, members of these crafts successfully petitioned the Mayor, Aldermen and Common Council for a charter of incorporation. In their petition, they cited their long association with the production of ‘The Shepherd’s Offering’ in the Chester cycle of Mystery Plays.

Amongst the Company’s best known members in the 17th century were the four Randle Holmes, heraldic painters, antiquarians and officials for the College of Arms. During the Civil War, Randle Holme II made hasty sketches of the City’s gilt plate, melted down to pay Charles I’s Irish troops. In 1655, he made the first recorded attempt to organise the City’s records.

In the 17th century, the Company met in the Phoenix Tower which was named after the painter’s emblem of a golden phoenix. During the siege of Chester, the Company was forced to abandon the tower because of ordnance planted on it. It was later restored to the Company which met there until c.1765. By 1835, its 23 members were meeting annually in a public house.