How cool do you have to be to get away with "unusual" headwear...?

...the answer is easy VERY COOL. I have headwear issues. Even when I ski I feel uncomfortable in my woolly hat. It may be my asymetrical ears or misshapen head but more likely it is the attention that headwear can bring. Sometimes it is unwanted, people misunderstand your fashion choice. Sometimes it is appreciative, a mutual love of the "different". I would looovvve to be cool enough to get away with these looks below but my fashion courage (and more importantly my self-esteem) aren't that high yet! If you are brave enough check out Urban Outfitters looks here. When my braveness arrives I shall post some celebratory photos!