How do you decide what will last for you and what is too trendy? I was watching a Seinfeld episode and realized that Elaine's clothes look SO dated to me now, though when the show was actually running she looked super-classic in that rich-girl boarding school way. But could we have known then that the look would pass? And how willing are you to buy something that is going to be done next year? (Maya, I think I know what you'll say!)... Or is everything doomed to be passe?

I struggle with this issue often - I'm pulled toward trendy but often have no idea how to make it work for me in any real or long-term way. Or I have no idea WHY something looks dated, especially with shoes. Square toes vs. almond? No clue.