Oh, fun post! I'm another Audrey fan, but my favourite is Funny Face- probably because there's just so much fashion in that movie!
Kristen, it's so funny that you mentioned Baby Boom, it's one of my favourite obscure movies. Nobody my age has ever heard of it, but for some reason I just love it. I think Diane Keaton rocks no matter what she wears. I would never wear the same things as she does, but on her it looks right. I like that she's an individual.
I'll second Mad Men, especially for interiors. I love me some mcm.
My style influences tend to be more subtle and random when it comes to movies, and probably hinge more on the movie than the fashion. For instance, my favourite movie growing up was The Sound of Music, and to this day I love anything that looks like it belongs in that film. That goes for 30's-style day dresses, florals that look like they might have once been curtains, and that whole soft, muted palette that the film is shot in. My sister always teases me for this, she calls it "the Liesl factor".
Not a movie, and definitely a cliche, but SATC is a big one for me, too. It was big during late high school/early university for me, and was a huge influence on how I played around with my look at that time. I love catching old episodes on late-night TV here. Sometimes Carrie looks amazing, and sometimes she looks ridiculous, but it's always fun.