5. Karl Lagerfeld
Brand: Chanel, Fendi, Karl Lagerfeld
The man may be regarded as a living deity, but he dresses like a goddamn weirdo. If you've ever read or seen an interview with him, you've come to expect strangeness out of the man, and sartorially he does not disappoint: the gloves, the sunglasses, the collars! Karl has undoubtedly been one of the most successful and profitable designers ever, but he also kinda looks like Rufus from Bill and Ted's Excellent Adventure.