The 10 Most Infamous Prom Dresses in Pop Culture History

While there are some dresses that never go out of style, prom looks seem to be very hit or miss and are regularly changing with the trends. Some of these 80s and 90s styles may make you want to go for a retro vibe this prom, others will have you thanking your lucky stars that you were born in this generation.

10. Josie Geller in “Never Been Kissed”


Hate to be a bully, but did you really expect to get anywhere in high school in a dress that looked like that? That dress looks like Little Bo Beep decided to work the corner in the 80s… and not in a good way.

9. The Girls of Laguna Beach


In 2004, aka PacSun’s hey day, California style was the *~coolest~*. Unfortunately, these prom dresses were VERY questionable. First off, isn’t the point of prom so that you can finally have a reason to don a long dress? Second off, while Kristin and Lauren’s choices may be the most flattering, they very closely resemble the plethora of skirts I bought from Wet Seal in the eighth grade.

8. Ling Ling’s Mom from “The Hot Chick”


Ling Ling may have forgotten her bling bling (she looked bomb, btw), but that doesn’t give you an excuse to show up to prom wearing an Adidas track suit. Sure, Adidas has become super trendy and has recently become a signature “model off duty look,” but you still can’t pull it off at prom, especially not in 2002, sorry.

7. Andie in “Pretty in Pink”


Oh, Andie, didn’t anyone ever tell you that redheads look better in cool colors? To give her credit, Pretty In Emerald wouldn’t have the same alliteration. But seriously, couldn’t you have shown off your waistline or something considering how excited you were for prom?

6. Sharpay Evans in “High School Musical”


TBH, I never saw High School Musical 3, but that doesn’t mean that in any world this dress is acceptable. Ashley Tisdale literally looks like a life-sized Barbie doll, and not in a good way. Although she seems to be surrounded by men and feelin’ herself, her obsessively matchy-matchy hot pink outfit is still deeply concerning.

5. Mary Kate & Ashley Olsen


Mary Kate and Ashley supposedly skipped their prom to host SNL in 2004. What I’m still trying to figure out is if these prom dresses were a part of the joke, or if they were actually supposed to be cute?

4. Bella Swan in “Twilight”


Do you think she borrowed this dress from Taylor Swift’s closet when the movie came out in 2008? Or was it purchased online at Delia*s? Either way, I think we all hated Kristen Stewart in the Twilight movies/books, and her fashion sense didn’t help her case.

3. Janis Ian in “Mean Girls”


TBH, this was not a bad look. I mean, the suit to prom look has gained serious momentum this year, and who doesn’t want to take their gay BFF to prom? Sure, I’d probably opt for something a little more form-fitting, but you go Glen Cocco, or Janis Ian, whatever.

2. Courtney Shayne in “Jawbreakers”


In Jawbreakers, Courtney Shayne looked bomb af in this dress before she got caught for accidentally killing her BFF. The sash may be a little much, but if someone were to gift this dress to me on prom I wouldn’t hate it.

1. Priscilla in “Not Another Teen Movie”

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I couldn’t find a last name for this queen bee from Not Another Teen Movie, but I could find this sexy photo of her in this dress. Sure, it might be a bit Britney Spears-ish from her “Oops I Did It Again” music video, but is that ever a bad thing? The 90s are totally back anyway. If some high schooler invited me to prom and I decided to cougar it up, I’d totally rock this dress.

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