Thanks, Neatorama! and TIME!
I didn't realize the squirrel was a boy. 1940's crossdresser.
This Year's Model Tommy Tucker was a squirrel adopted by a woman in Washington, DC, in the early 1940s after she found the critter orphaned in a tree.
He soon became part of the family, as it were -- accompanying the lady of the house on shopping trips, for instance. She also, it turned out, enjoyed dressing him up in specially made outfits. And so it begins ...
There is also a game.