10. Big Floppy Huck Finn Hats
What Your Son Will Say: Why is mom wearing the same hat in that picture that great-Uncle Seymour wore while sharecropping?
What We Say: Women have an uncanny ability to make the worst possible hats the latest fashions. If you thought the whole fedora thing was bad enough, just try to understand why all these ladies want to look like they're about the head down to the ol' fishin' hole, tie some line to their big toe, and chew on some wheat grass as they idle the day away.
The Adventures of Huckleberry Finn might be a great work of literature, but that doesn't mean that it's to be used as a style manual. Unless your girl is setting up a whiskey still in your studio apartment, she really ought to steer clear of these.