When did those first weird Old Navy advertisements start coming out? I think they featured Morgan Fairchild. And there was also an elderly woman with big glasses – I think I was meant to know who she was but I didn’t recognise her.
I’m assuming that the style of the ads references those cheezy, old “holiday special” programs, like Perry Como and such.
Don’t have an answer to your question, but the woman you’re referring to is (was) Carrie Donovan. She was a fashion journalist, first as a reporter for the NYT, and then as an editor for Vogue, Harper’s Baazar, and NYT Magazine.
Most people who see her have some vague sense of recognition. But if you don’t follow fashion journalism, you probably wouldn’t know exactly who she was.