More likely a milkman than a conductor.
Me again. The Elsie's Good Food Line promotion (c. 1952-3) did, however, involve a train (http://digital.hcplc.org/burgert/archive12/11726.jpg). It looks like the kid on the left is wearing a punch-out conductor's hat with cow ears (probably Elmer's). The kid on the right seems to be holding one in his lap (no fool, he).But the adult's cap just doesn't look like an engineer's cap or a conductor's cap.
Thanks for your comments and info. You're right, his hat does look more like the typical milk delivery man's hat.
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