I have a particular love for any film in which a duo is on the run, why? I suppose I have some secret desire to live the life of an outlaw, and yeah, their clothes are always pretty good. Bonnie and Clyde is the obvious choice. Faye Dunaway in camel berets and silk scarves, yes. Warren Beaty in pin stripe suits, double yes.
Another favorite film in the genre, Thelma and Louise. This is the only time a confederate flag tee shirt is appropriate, high rise acid washed jeans and cowboys hats, it's all pretty great. I can't watch this film without developing a twang, and calling up my best girlfriend to plan a roadtrip in which we fly through the desert in an old school convertable taking out our agression on "bad men". Obviously ludicrous but looks so fun. And let's not forget Brad Pitt's involvement in this film, back when he was the go to hot guy, for good reasons.
Badlands! My boyfriend introduced me to this film a few years ago and since then I constantly want to watch it. Martin Sheen picks up poor little Sissy Spacek and together they take their love on the road making big trouble along the way. Spacek wears sweet little sundresses and Sheen takes on the classic badboy look of the 1950's a la Marlon Brando. Let's not forget Kalifornia! Juliet Lewis and Brad Pitt join up with a couple researching serial killers and travel across the country not knowing that Brad Pitt is a killer himself. Juliet Lewis wears baby barrettes and slip dresses, the epitome of ninety's fashion. While we are on the Juliet Lewis is an awesome chick train let's talk Natural Born Killers. This movie is nuts and full of awesome out there fashion! Mickey and Mallory are celebrity criminals on the run and it all just gets well, crazy. Mallory takes full advantage of her infamy changing her look and wigs regularly with much joy. Yes, all of the movies are a bit over the top and violent, but seriously, the costumes are good!