Grand-daughter of the Fine Antique Photo To Ponder

[GinaC]

That hairstyle screams 1940's. It was called a "victory roll", though hers looks somewhat tousled, probably because helmets weren't legally required back then.

EDIT: Though, upon further inspection, it could also be a "suicide roll" from the 50's.

[phil]

my brother restored one like it , a 1942 harley 45. springer front end, pogo seat. he sold it and it's in a museum now. some were military bikes in olive drab, or cop bikes but there were civilian models. so could be army surplus. sidecar was an option. the jacket might fit but the shoes.. these were not electric start. Jolly rogers and perfect hair say the pic is staged. she's so pretty! lots of headlights and the chrome on the front fender might be added trim. the cop bikes had a siren.
compare it to john boys' bike it had a sidecar. the shifter is on the side of the tank. one of the handgrips controls the distributor advance.
splash system, no oil pump.
I think this bike is bigger, maybe a nucklehead but the real harley aficionados would know better. that teardrop badge on the tank probably is enough to date it more accurately.