Since it was released in 1986, Pretty in Pink has become one of those iconic movies that’s been watched at many a slumber party or girls’ night across the globe. Amongst the many debates that the movie has brought up - Can two people from different sides of the track really fall in love? Was Molly Ringwald’s hybrid prom dress that much of an improvement over the original one? - there is one element that almost all the fans of the movie can agree on: Phil “Duckie” Dale was the stylish guy friend that we all wish existed in real life, both so we could befriend him and raid his wardrobe.

Played by a younger Jon Cryer (yes, that’s the guy from Two and a Half Men, but we’re trying to ignore that), Duckie manages to accomplish an impressive feat: standing out in a stylish cast that included Molly Ringwald’s turn as Andie, a thrift-store-junkie-turned-seamstress, and Annie Potts’s portrayal as the spiky haired record store employee named Iona.

The first part of Duckie that we see in the movie are his Chuck Taylor clad feet, strutting down the hall of his high school. As the camera pans out we are given full view of what can only be described as the Greatest Outfit of All Time Ever: black slacks, a floral print collared shirt, a chequered vest, a plaid blazer, a bolo tie, several rings and pins, teashades and a fedora. The average person would probably not be able to handle such an over the top (yet totally charming) mishmash of patterns and accessories but for Duckie it is just another Monday morning, and a preview of more amazing outfits to come in the movie.

He rides his bike while wearing a boater hat and a plaid shirt over a printed tee, a concoction not unfamiliar to a recent Marc Jacobs show. He successfully captures the hearts of many a teenage girl while performing a rousing lip synch of Otis Redding’s Try a Little Tenderness in a yellow sport coat and creepers:

Duckie was the sort of guy who was not afraid to stand out in a high school that was dominated by preppy kids. His clashing patterns and infinite layers of clothing leads me to believe that he and I share the same style philosophies when getting dressed in the morning; I can almost picture him pouring in front of his closet, deciding whether his newly thrifted vest would look better with his plaid or his floral shirt, but ultimately just not giving a damn about what the other kids (save Andie) think of him. After all, this is the kid who would wear suspenders and plaid pants to class, and a blue brocade suit and a bolo tie to prom.

Duckie’s “competition” in the movie in vying for the heart of Andie’s affections was Blane, the sort of fellow who would wear plain tee-shirts and coats. If this was not a fashion centered post I would go on about how Andie is stupid for picking somebody who probably didn’t even know who Otis Redding was over the epicness that is Duckie, but I will refrain going off on a tangent. Instead, I will point out that sartorially, Blane’s khaki ensembles aren’t half as cool as one of Duckie’s floral suspenders. Not that we’re advocating judging people based on their wardrobe choices, but if you were Andie who would you pick?

Thought so.

-Anna Fitz