The little girl on the 1963 calendar hasn’t aged in two years and is still carrying the same fresh-faced Teddy bear, whose eyes always seem to be looking in the same direction as the girl. Her slip is showing beneath her wind-blown dress as she is about to board the Hiawatha behind another little girl whose slip is also showing.
Click image to download a 1.2-MB PDF of this calendar top.
In 1965 most people probably thought this was cute, but in today’s hypersensitive atmosphere it seems pretty creepy. Though most of Milwaukee’s calendar artworks from the 1950s were signed, the ones from the 1960s were not, so I have no idea who did these paintings or whether it was the artist or the railroad marketing department that was more obsessed with prepubescent girls.
Weird, mom has no (visible) tattoos or piercings.
Her ears may be pierced. Funny how we think of pierced earlobes as “normal” while other piercings are “extreme.”