How do you dress "radically" (opposite of conservatively)?

I acknowledge the question is not the most clear so I'll try to explain what I'm thinking. Lots of fashion is influenced by military or classist tradition (collars, ties, "sharp" looking pants with straight lines/creases, etc). Work wear is a bit more proletarian, with hard wearing fabrics (that can fade/age tastefully), looser fits, and so on. But even that has taken a form/tradition of its own. How can men dress less conservatively? Other than going full drag? (Keeping open some room for gender neutral expression) Any examples of accessible designer or retail outlets that provide such looks?