When things get tough around here, there’s one film that always gets popped in the DVD player. I must have seen Pretty in Pink about a gazillion times… well, at least fifty. Sure it sounds silly and slightly OCD, but since it came out in 1986, that’s about twice a year, on average, although the first time I saw it was in the late ’80s, a few years after it came out. The funny thing about watching this film as a pre-teen is that all I could concentrate on was Andie (the lovely Molly Ringwald!) being poor, because that seemed like the worst thing to be in high school. Then, when I watched it in high school, I realized that she may have been poor, but that she was the cool kid — and that’s probably what we all want to be.  She may have not been seen as cool by her peers, but Andie worked at a record store and she had a cool older friend that wore weird outfits and smoked cigarettes: that was good enough for me.

Of course, much of plot focuses on Andie camouflaging her poverty with idiosyncratic thrifted-and-reworked ensembles. Costume designer Marilyn Vance (who was also responsible for two of my other favourites, The Breakfast Club and Pretty Woman) provided a considerable amount of vintage florals, but then mixed them with off-beat contemporary pieces like the “Korea” varsity jacket Andie wears to visit her older bestie, Iona (who lives in the coolest Chinatown apartment, of course!), to inherit her prom dress. Andie’s final design was, well, very Andie, and to this day there are conversations about whether or not it was hideous. Far from, I think! I’d wear it now. According to this Dazed & Confused interview with Vance, she admits that Molly gravitated towards the hideous opinion.

“She hated that dress! Molly actually hated it with such a passion you have no idea. A lot of her clothing as Andie Walsh I found in thrift stores, so I cut up two dresses to make the prom dress – just like she does in the film. Poor John Hughes, Molly’s in her trailer with her tutor, she hates the dress and he’s whining to me ‘You can’t make her do that, she hates it.’ I said ‘Andie is not going to wear like, a Madonna dress. And she’s not going to dress like the other kids, she’s an individual. She’s pulling clothes apart and making her own style.’ And John decided, OK that’s it, Molly is going to wear it…”

But, the real question is this: did Andie choose the right guy in the end? Sure, Blaine was dreamy, but Ducky was pretty damn cool. John Hughes certainly knew how to write teenage characters like no one else.

Images via BuzzFeed and Dazed.