Gotta love 'em crazy

Hi! Popping in to report I had a wonderful sweet 16th, I am ever-expanding my shoe collection (can't exactly help it, either), falling in love with crazy hipster-esque/Cobrasnake-ish accents, can't stop stealing my brother's vast collection of graphic tees and a costume party is coming up! What do I do with this? Ideas, ladies (and non)?

Would you rather be caught dead? You dig? What exactly does one wear with it?
(I sort of dig it. And maybe in the midst of purchasing..)

[source, tFS/Topshop]