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 ...