Hey Bees, you can be as ridiculously obscure as you like. Souwesters is at least one word, which, if the clue is correct it should be and it certainly isn't any more obscure than "juliet caps". I am personally coming to the conclusion that the answer won't have anything to do with hats at all. I keep trying to think what else could be "two extremes". I have poles, ends, hot/cold, north/south, east/west, ice/fire etc. etc. so I am taking a different direction to see if that makes a difference.