George's wife Helen died in 1822 and it would seem that Margaret died at a young age. By the 1841 census George (who is described as 'living on independent means') is found residing with his second daughter Janet in Kirkton of Largo. Meanwhile, eldest child, Helen, is married to a William Wood who is described as a tailor and clothier in consecutive censuses. It is likely that Helen and William took the business over from George Simpson upon his retirement. The business must have been fairly substantial, as in 1851 Wood employed 5 men and in 1861 he employed 4 men and 2 boys. By 1871 Wood had retired, being described as a 'late tailor'. In fact, the 1865 valuation roll also describes him as a 'late clothier' who owns three consecutive properties on Upper Largo's Main Street - one in which he lives and two in which other individuals are carrying out a tailor and clothier business and a drapery business respectively. The shop continued to be a tailor, under different names, for many decades thereafter.
The location of the tailor's shop, and of George Simpson's original premises for his business as a draper and clothier, is on the south side of the Main Street, just to the east of the Inn (now the Upper Largo Hotel). The business therefore would have been in the shop on the right side of the photograph below (shown in more detail further below). George Simpson was granted the feu from Major General James Durham of Largo on 1st November 1809. Simpson set up his business at a time of development in the village. The main road had not long been upgraded and the Largo ferry would soon bring new visitors to the area. Over the years, as his drapery business thrived, George Simpson developed other business interests. He had shares in the Leven Gaslight Company, Largo Inn and Granary and in Largo Granary Steelyard at the time of his death.
"George Simpson, Clothier of Largo died 27.6.1847 aged 76years. Helen Mackie his spouse died 17.12.1822 aged 52 yrs. Son John Simpson d 19.10.1840 aged 30 years. This stone erected to their memory by their remaining daughters".