When a film calls for a beautiful actress to temporarily not look like a beautiful actress, filmmakers are met with a conundrum. There's a fine line they need to toe. They don't want to go all Charlize Theron in Monster, with the prosthetics and fake teeth, but the actress needs to look like she's made some sort of transformation. "How do we make this gorgeous woman look like she's wanting for male attention and a trip to Sephora?" they ask. The solution, it seems, is to simply slap an ugly sweater on old girl and call it a day.
Fifty Shades of Grey
In addition to BDSM, Christian Grey apparently teaches Anastaisa Steele about the wonders of a good conditioner and that room temperature can be perfectly comfortable without a sweater.
Now, Sandy Olsson wasn't meant to be unattractive or dorky in the first place. She was just a preppy cheerleader before she went Bad Girl Riri on Danny Zuko. They needed some sort of contrast to the days after she discovered red lipstick and got a perm.
It's not exactly a cardigan, but Cady Heron's ugly brown jacket might as well be. Other than the little black dress and the smile, the only difference between "before" Cady and "after" Cady are the use of some hot rollers.
Maid in Manhattan
I love when Jennifer Lopez pretends to not be gorgeous. I like to think that because she's so beautiful, one cardigan just wasn't enough, so they layered those suckers up and added a turtleneck just to be safe. But the baby hairs don't lie.
Tai Frasier's baggy flannel? I'll count it in the cardigan category. Funny enough, Tai continues to rock cardigans post-makeover, proving that it is the girl who makes the cardigan, not the other way around. Take note, costume designers.
You can tell that Baby is sexually liberated now because she cha-chas in an exposed midriff. Can't cha-cha in a wool sweater.
A Walk To Remember
Jamie Sullivan's sweaters are actually a plot point of their own in this film. There are numerous references to the preacher's daughter's affinity for muted cardigans and I'm pretty sure the only time we see her shoulders is during the scene on the right. Of course, her character does have cancer, (spoiler alert from twelve years ago) so, I'll just leave that alone.
She's All That
An ugly shirt at the beach counts, Miss. Laney Boggs. (Did that name seem as ridiculous at the time?) To be honest, it doesn't feel like they made much of an effort to disguise Rachael Leigh Cook's cuteness. They thought those heavy brows and glasses would do the trick but little did they know that the days of hipster glasses and eyebrow merkins were nigh.
The Devil Wears Prada
There is a whole sassy takedown dedicated to that blue sweater, which really isn't even that ugly when you think about it. It seems that Hollywood's solution to making Anne Hathaway not look like a doe-eyed knockout is to throw in a wool sweater and make it look like she lost her flatiron.