This piece on "menswear in the movies" (yes, I read flare.com, need my cancon!) gave me some titles to add to my videobuster list. However, I think #10 is streaching it a bit.
As a replacement, how about Whoppie Goldberg in like, every movie she's ever been in? The menswear look is so much a part of her personality, that just seeing her in a dress gets her a laugh (or an Oscar nod...)