Pickering's earliest known portrait is date-able to 1740. His typical style of painting is a stiffer rendering from that of Thomas Hudson. Vertue states that in 1745 Pickering returned from a trip to Italy and that he on occasion worked with Joseph Van Aken the drapery painter. He was working in London circa 1746, but also appears to have had a good following in the North Midlands. He appears to have moved about between Yorkshire, Lancashire, Cheshire and North Wales, all of which districts provided him with sitters. In 1759 he was living in Manchester, possibly in Deansgate and appears to have been there at his death.