Duckie Dale: Loyal Friend, Otis Redding Fan, Style Icon Extraordinaire

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

12 thoughts on “Duckie Dale: Loyal Friend, Otis Redding Fan, Style Icon Extraordinaire

  1. I’ve never seen this movie. though … now I want to.
    Must overlook the two and a half men relationship. That sitcom annoys the crap outta me. How is it still on.

  2. I LOVE this movie, I just saw it. I am madly in love with Duckie, and when Andy chose Blane, I went crazy. NOT OK! I love the characters and their fashion–you should do another post to follow up on the style of Iona! She’s my epic hero of life. Love love LOVE her, she sorta reminds me of my fairygodmother. :]
    And the prom dress Andy cuts up… oh my GOSH I get so angry every time… Its sooo beautiful and she RUINS it…
    Overall, an EPIC movie. :]
    xoxo Sprinkle

  3. Nice post, Anna! I wonder if there’s a special DVD release somewhere that has the original ending on it where Andie and Duckie do end up together. I would buy it!

  4. AAHH! I love this movie!!! One of my dreams is to be the modern Molly. This movie is up there with my other favs of the time: the Breakfast Club, St. Elmo’s Fire and Sixteen Candles- all MUST SEE!! Do it. And stylize yourself accordingly.

  5. Every time fashion takes its inspiration from the tacky old teenage movies, I am in awe. When this one came out I was 12 and didn’t see it because I thought it was too commercial. Now, when I see these photo’s, it makes me realize how literally we took the 80′s revival. I wonder why…
    I’m never gonna see this movie, I’m thinking this while rolling up the sleeves of my blazer. Suddenly, another tacky 80′s hero pops in my mind…

  6. I am so happy to have read this post. Duckie is one of the BEST movie guys ever and I did not then nor do I now even remotely ‘get’ why Andie would ever choose Blaine (“that’s not a name it’s a major appliance!”) Great movie, weird unexplainable things like why they took two gorgeous vintage prom dresses and hacked them into the worst pink potato sack dress. My sister and I still groan at the screen and ask “Why, Andie, why?” whenever we see it. I’m so glad to see that someone else thinks about these things too.

  7. I’ve gotta say, I hate many of Duckie’s ensembles (and Andie’s horrid pink dress mash-up; wtf was she THINKING?!), but the fact that he’s being himself in a sea of preppie fucksters like Blaine is what makes him Duckie and therefore loveable. He’s got his own fashion sense, for sure, and we wouldn’t want him any other way. Andie is an idiot for choosing the major appliance (as Jessi pointed out) over The Duck Man, but I guess the point here is that clothes do not make the man? I mean, we usually love people *in spite of* their lack of fashion sense, not because of it, right?

  8. I totally love people for their fashion sense. It’s a reflection – what you wear is part of who you are. I most certainly love Duckie’s outfits and love him even more for wearing what he does!

  9. this is my most loved movie of all time and i can’t believe worn published this!!! kudos for the otis redding scene too! everything about this is amazing!!!

  10. oh my . duckie where do i begin .
    nothing about him was happy . i remember saying to myslef . why don’t guys like ducky exist in real life ?
    is it too wrong to look for a guy like ducky ?

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