I know this is an old thread, but I like the idea. So I'll just throw out my opinions.
For my generation: the Monster line (yes, even the MD)
Classy: Shure SE530, Ortofon EQ-7, Audio Technica CK100
Cool/Funky: Westone 3, IE8
Sleek: Klipsch X10, Klipsch X5, Etymotic HF5
Ugliest: TF10, Earsonics SM3