Even though Damsels in Distress, Whit Stillman’s latest film, is set in a collegiate Oz rather than the Ivy League, he continues to have an unshakeable reputation as cinema’s Preppie ambassador. But preppie looks in the films—and on him—are in many ways simply an economical solution for a look that doesn’t age, as much a matter of penny-pinching as aesthetics. (Buying a few beautiful pieces and wearing them until they fall apart is a form of anti-consumerism.) So preppie in his films is a bi-product of a search for timelessness, appropriate for films that usually take place in a nonspecified moment in the past and seem, too, instantly like classics.
Stillman spoke with us about classic collegiate looks, his Rushmore-esque past, and his fashion advice for those with a “pathology of cheapness.”
The new film takes place on a campus. Do you have thoughts on classic American collegiate looks?
What is that book that’s so famous, Take Ivy? It’s a very famous book about American collegiate fashion.
The Japanese book?
Yes. It looks terrible. In my memory it was much better. I remember the old catalogs for my school, the Millbrook school, and everyone looked kind of woodsy and great. It was a very naturalist-oriented school. And it’d be interesting to see the old school catalogs from the early 60s.
Were the catalogs anything like the reality?
Absolutely. They didn’t have the budget to hire models. But I think my clothes, when I went away to school, my mother had bought at Giant supermarket, or something like that. It wasn’t very prepossessing.
But there was a really nice spirit in that school. It was crawling with people like Violet [Greta Gerwig's character in Damsels in Distress], actually, people who seemed really off-putting but they were actually really kind of nice and sweet. I remember coming from a school in Washington DC that was supposed to be really right on and political and correct; people were really mean to each other. Then I went up to Millbrook, and I remember a guy coming to my room and opening my closet and checking out my clothes. People there would be very competitive and observant. It was fun mocking. But it didn’t make you feel bad. It was being included.
What about sneakers and or sweatshirts? Those are kind of classic collegiate looks.
Oh really? [Faux-innocently] You know, I’ve never worn sneakers or sweatshirts in my life. And I wore blue jeans—pretty much the same pair of blue jeans—every day, throughout college. And I decided the moment I graduated from college that I would never wear blue jeans again. And I have never worn blue jeans again.
The tuxedos that you used in Metropolitan, created such a distinctive look—black and white in color—and created a sort of code, everyone dressed alike, and a specific world for the film. I heard that you got them for free?
That was one of the key things about that production. Because one of the ideas of Metropolitan was we could the actors dressed formally, and it would look different from all the other independent films; it wouldn’t look like a typical Sundance film. (Which was a problem, because we almost didn’t get into Sundance.) We thought this could be very cinematic, very minimalist and cinematic. So it would be these very dressed up characters talking in a very rich, plush room. And the whole story came from that.
So the key thing was to get these clothes. So I said to someone on the production, go to A.T. Harris. And she went to A.T. Harris, and he loved her—she was a really charming girl—and he said we could use all the evening clothes we wanted, for free. Also we had a scene that we wanted to shoot there, and he was the tailor. He said that he made so much money from Metropolitan, that he bought a country house. Metropolitan was the perfect ad for A.T. Harris.
Next: Whit’s Guide to Style