Making costumes is one of my hobbies, so I've bought a lot of random stuff (wigs, shoes, stockings, other accessories), but on its own none of it is too off-the-wall. Probably the oddest individual item was a cheap red fedora hat that had a blue sequin band and feathers...

...but I ripped the sequins and feathers off, replaced it with a plain black fabric band, wore it with a red trenchcoat, and was Carmen Sandiego for Halloween.