It occurred to me that no one uses the expression "handsome woman" anymore, and if my long observation of American culture can be trusted, the sequence was:
1. "Handsome woman" was once a standard expression, used as a genuine compliment for a particular kind of woman. Ah, here's something from 1783, "The Distinction Between Words Esteemed Synonymous in the English Language":
"By a handsome woman, we understand one that is tall, graceful, and well-shaped, with a regular disposition of features; by a pretty, we mean one that is delicately made, and whole features are so formed as to please; by a beautiful, a union of both."2. Because "handsome" was the standard word to refer to a man's appearance — you wouldn't call him "pretty" or "beautiful" — calling a woman "handsome," it was too easy to sound as though you were saying that the woman looked like a man, and nice people started to feel inhibited about saying it.
3. Only not-so-nice people were left saying it. We laughed watching "Seinfeld," when Elaine said — about George's girlfriend who looked like Jerry — "she's quite a handsome woman." And here's Captain Kirk in 1966:
4. The joke/insult use died off because the original, serious usage no longer existed. You have to have the reference point to make it funny, and the envious deployment of an incomplete compliment doesn't leave you unscathed if you use a word that nobody nice ever uses.
5. Here we are in the present, where the word "handsome" could be revived. And why not? There should be no stigma in a woman looking good in a way that tends toward the masculine. And it shouldn't be bad for a woman to look good in a way that doesn't highlight sexual accessibility. That's the look many woman like and might seek to enhance rather than to overcome.