According to Alison Lurie’s inventive book about fashion, The Language of Clothes, trying to dress younger than you are has long been regarded as a bad fashion move. “Since classical times, literature has been full of elderly and not-so-elderly comic characters who affect the costume and manner of youth.” While men are also the targets of ridicule, there is a well worn phrase for older women who transgress.
Helen Hokinson, cartoonist for the New York from the mid 1920s to the late 1940s, had a keen eye for the missteps of women of a certain class (and post-menopausal heft). One of her running gags shows these women trying to keep up with current fashion, often with the sly aid of a much younger saleswoman.
This cartoon comes from Hokinson’s posthumous collection The Ladies, God Bless Em! Although drawing isn’t dated, I believe it comes from the 1940s, when pants and shorts as casual attire gained popularity, especially among younger women.
The woman here is meant to look ridiculous, in her odd overall shorts combo worn with old lady shoes and elaborate jewelry. And what would the husband make of such an outfit? Detached and baffled husbands are another standing joke for Hokinson. Perhaps somewhere there is a drawing of the hapless woman showing off her outfit to her astonished spouse.