Hmm,I'd say Lady Gaga
Personally i''d make my boyfriend go as something recognizable by everyone such as barbie or wonderwoman! , or you could make it over the top and dress him up as a drag queen ! bold bright makeup etc
Go as Roger Rabbit, and make him be Jessica.
Marilyn Monroe
Something embarrassing and remember able so people could say years later, " hey remember when so and so dressed their boyfriend up as a girl for the costume party?" And the person would laugh their socks off.
Cher or Madona with those weird bras.
the little mermaid would be perfect. :)
Alice in Wonderland! Or a girl that suits his personality or look! c: