I get a lot of comments about certain outfits that I have shot don't work in the "real world" - I think the people making those comments are just not considering all the jobs people do that allow them their Sartorialist freedom.
I shot both of these today in Soho about a half hour apart. They were both pretty surprised when I was able to guess what they were doing.
Example #1
Any guy dressed with that level of style, carrying a mirror (not on Flea Market Sunday) must be prop buying - he was, for the John Varvatos store.
Example #2
Wearing a vintage piece like that and carrying several big bags of clothes she was obviously returning samples from a photo shoot.
I guessed on both and scored big points by being able to guess.