To Rosie, your friend John
John is wearing a jaunty cap with a winter double breasted overcoat with the upturned collar. His boots have buttons on the sides and raised rounded toes popular from 1910 on they called bulldog toe or American Boston. Aren’t they nice? It looks like the shoe style with the rounded toes came into fashion around the end of the 1900s. His pants have creases and cuffs. I’d date this one from the mid 1910s to maybe the early 20s.
What letter or postcard is John reading? The pose is unusual and a creative idea. The receivers of his correspondence wouldn’t have to imagine him reading their letters.
RPPC: CYKO 1904-1920s