When he was young, Simon was apprenticed to a tailor. Upon completion of the apprenticeship he set up his own business in his hometown, Great Missenden.
In the 1841 and 1851 census of Great Missenden, Buckinghamshire, England his occupation was listed as tailor &c. I am assuming the "c" means clothier.
The 1861 Boston, Lincolnshire, England census lists him as a clothier, while the 1871 and 1881 census list him as a retired clothier.
While I was scouring old newspaper archives I was lucky enough to find a couple of ads.
|Lincolnshire Chronicle, Dec 18, 1863, page 2|
|Lincolnshire Chronicle, Dec 25, 1863, page 2|
Not only was I able to find these ads, but I found others that indicated he sold other things besides clothing. It turns out that Simon was also a tea agent, and according to the 1844 Pigot & Co directory, he was also a fire insurance agent as well as a tailor.
|Bucks Herald, Oct 17, 1846, page 2|
I guess when you have a shop, you're going to sell what you can, right.