The Worst-Dressed List: Movie Character Edition
One of the best things about going to see a new movie is sitting and marveling at the costume designs. There’s an entire Academy Award category dedicated to just that. Unfortunately, not all wardrobes are created equal, and some characters get the short end of the fashion design stick.
From the bright orange and blue tuxedos in Dumb and Dumber to pre-fab Andy in The Devil Wears Prada, here are some of the worst-dressed movie characters of all time. Trust us; these fashion choices all need to be on an episode of What Not to Wear.
Edina And Patsy In Absolutely Fabulous: The Movie
For publicist Edina Monsoon and her best friend Patsy Stone, being Absolutely Fabulous also means being absolutely basic. These two ladies take the phrase “over the top” and literally run out the door, across the country, and to the other side of the world with it.
From their extravagantly patterned leggings to 100% metallic outfits, Edina and Patsy are definitely some of the worst dressed people in film. But, hey, at least they own their looks and don’t care what other people think!
Deb In Napoleon Dynamite
When someone comes up to you and says, “I like your sleeves,” in the back of your mind, you should probably know that your sleeves are probably a bit funky. In Deb from Napoleon Dynamite‘s case, they were more than a bit funky. The girl’s epic side-pony and puffy sleeves were straight out of the ’80s and most definitely not high fashion.
None the less, she is still a perfect match for the geeky Napoleon. We mean, can we talk about that large, puffy, pastel pink dress she wears to the school dance? It suits her just fine but isn’t going to help her win Homecoming Queen anytime soon.
Miss Hannigan In Annie
In the 1982 musical Annie, Carol Burnett’s character Miss Hannigan was a bit difficult to overlook. Not because she was the head of the orphanage and was trying her hardest to exploit the children for money, but because of her gaudy attire.
Seriously, if there were ever a villain who had a wardrobe that reflected their personality, it would have to be Miss Hannigan. She had everything, from feathered sweaters to her double wrapped long necklace. Everything she wore just oozed sleaze.
Andy In The Devil Wears Prada
Before Andy showed her boss at Runway magazine that she knew a thing or two about fashion, she looked like she walked out of an American Girl Doll photoshoot, and not in a good way. We’re talking oversized skirts that did nothing for her figure, chunky oxfords, and layered crewneck sweaters that should never have been a fashion trend (were they ever?).
Either way, she thankfully got some much-needed help in the fashion department, completely transforming her look and confidence. We call it pre and post-Andy.
Lloyd Christmas And Harry Dunne In Dumb & Dumber
Now, the thing with a film like Dumb & Dumber is that you have to take Lloyd and Harry for who they are — two grown men who are just a bit slow and drive around in a van that looks like a dog. Because of this, it shouldn’t really come as much as a surprise that they’re on the “worst dressed” list.
Seriously, they wear bright blue and orange tuxedos to a black-tie event, complete with top hats, ruffled blouses, and walking canes! Ironically, they thought they looked quite dashing in their get-up. To each their own, we suppose.
Shelley Darlingson In The House Bunny
After her 27th birthday, Shelley Darlingson gets kicked out of the Playboy mansion. The thing is, when a person is kicked out from being a Playboy bunny, one would think that person’s wardrobe would change. Nope! When Shelley became the mother of a college sorority, her wardrobe stayed pretty much the same.
We’re talking mico-mini skirts, tops that are most suited to be a swimsuit, and stiletto heels that add about a foot to actress Anna Faris’ tiny frame. All in all, her wardrobe needs a little bit of an update and maybe a bit more material.
Bonnie Parker In Bonnie & Clyde
Although Bonnie Parker doesn’t look horribly dressed to go on a spree of crime with her lover Clyde Barrow, the women of the time absolutely loathed her attire. When Bonnie & Clyde was released in 1967, women’s fashion trends were changing. The midi skirt and long-sleeved shirts Bonnie wears in the film was no longer “en vogue.”
Instead, the mini skirt was coming in to play. So, for ladies watching the film, Bonnie’s outfit looked like nothing more than something an old lady would wear. And that’s not a good thing considering Bonnie Parker is supposed to be this femme fatal.
Andie Walsh In Pretty In Pink
Before Selena Gomez made “granny chic” cool, there was Andie Walsh in the rom-com Pretty in Pink. This high school outcast might have been creative with her wardrobe choices, but that doesn’t mean she doesn’t have more chunky sweaters than absolutely necessary.
And if you tack on the fact that she paired big round glasses, buttoned-to-the-neck patterned blouses, with boxy skirts and clunky oxfords, and you have one character who you’re not surprised is considered an outcast by her peers. Even so, Andie owns the look.
The Flawless Four In Jawbreaker
The thing about “The Flawless Four” in Jawbreaker is that they really weren’t all that flawless. The ladies making up the high school clique were a little too into themselves, and their outfits were nothing to write home about. Instead of looking like teenagers, these gals were more into the secretary look.
Pleather heavy, pencil skirts and tiny sweaters over even tinier under shirts completed their bright and gaudy looks. Whatever happened to the typical high school dress code of jeans and a sweatshirt?
Jamie Sullivan In A Walk To Remember
When you’re known as the girl who always wears a pastel-colored sweater, sorry, but you’re going to be placed on “the worst dressed” list. In this particular instance, the character is the one and only good religious girl from A Walk to Remember, Jamie Sullivan.
The thing is, we can’t even fault her for wearing oversized, floor-length dresses with her light pink sweater because it goes perfectly with her character’s personality — sweet. But that doesn’t mean we have to like it. She’s still pretty poorly dressed!
Dawn Wiener In Welcome To The Dollhouse
Middle school is an awkward time for the majority of people. So, it kind of makes sense that the character of Dawn Wiener in Welcome to the Dollhouse is all over the place when it comes to fashion. From high-waisted track pants with a tucked-in graphic t-shirt to “my grandma definitely knitted this for me” sweater, Dawn is most definitely one of the worst-dressed characters to come off the silver screen.
The thing is, Dawn’s just so cute and quirky that she kind of makes the electric color palette and plastic accessories work!
Priscilla In Not Another Teen Movie
While Not Another Teen Movie is technically spoofing all of the teen movie stereotypes, including wardrobe, it doesn’t mean Jaime Pressly’s character Priscilla is getting off the hook. This character literally plays into all of the popular girl patterns, including the absolute cheese that is her costume.
We’re talking low-rise jeans with a patchwork pattern, pin-straight blonde hair, a spaghetti strap tank top (pink, of course), which is complete with a lovely feathered accent. Needless to say, it’s not a good look.
Enid And Rebecca In Ghost World
Enid and Rebecca in the comedy-drama Ghost World is a perfect example of teenage angst translating over to clothing. These two characters go all out, wearing quirky mini skirts, graphic tees, chunky boots, and a whole lot of plaid. Honestly, we didn’t even know someone could have so much plaid in their wardrobe.
And while Enid and Rebecca’s style can be categorized as hipster, it still places them on the list of some of the worst-dressed characters in film. Then again, they do get some props for being hipster before hipster was a thing.
Toula Portokalos In My Big Fat Greek Wedding
Before she decided to turn her life around and give herself a much-needed makeover, Toula Portokalos was pretty much lost in the wardrobe department. No one should subject themselves to an all-brown outfit, especially if that outfit happens to be a shirt and sweater with matching pants and hospital-grade rubber shoes.
Thankfully, she eventually ditched the bulky attire, turtlenecks, and brown-rimmed glasses for something a bit more flattering, eye-catching, and, hey, she even learned how to put in contacts.
Laney Boggs In She’s All That
If you need help figuring out who the outcast high school student is in the film She’s All That, look no further than the character wearing a printed button-up shirt over baggy jean overalls and thick-rimmed glasses, aka the artsy girl named Laney Boggs.
The ’90s film definitely played off the high school stereotype. But Laney made the look work! Unfortunately, her loner status also made her the perfect target for the “I can make her prom queen” bet.
Josie Geller In Never Been Kissed
Not to say Josie Geller doesn’t have a stellar personality, but the fact that she wore some of the most garish outfits known to humankind probably didn’t help her whole Never Been Kissed situation. And while we can sit here and dissect all of her wardrobe choices, we’re going to stick to one: her prom dress.
Now, this is no normal prom dress. Josie was able to find one that looked as though it’d been designed from tinfoil satin. Add in the princess waistline, sleeves as puffy as her head is big, and you have a dress that is anything but subtle, even for the ’80s!
Allison Reynolds In The Breakfast Club
Allison Reynolds is the loner in the misfit group making up the Breakfast Club. And, as such, she is apparently destined to be dressed in such a non-subtle way that the costume department might as well have had a neon sign flashing above her head saying, “outcast.”
Honestly, the all-black clothing wouldn’t be horrible, but the fact that nothing fits her properly and there’s a heavy parka-type jacket concealing her body makes it pretty awful. Even so, the horrible dress doesn’t sway the fact that Allison is a pretty cool character that finds her confidence after a much-needed makeover.
Janis Ian In Mean Girls
If The Breakfast Club were made in the 2000s, then the character of Allison Reynolds would most definitely be the cool and edgy Janis Ian from Mean Girls. The thing is, Janis can have an “I really don’t care about anything” attitude all she wants, but it doesn’t change the fact that she is one of the worst-dressed characters in film.
Layered t-shirts over long-sleeved shirts, skirts over pants, and let’s not forget the purple suit she wears to prom, Janis did the impossible — she made the gothic style gaudy.
Bridget Jones In Bridget Jones’s Diary
The thing about Bridget Jones in Bridget Jones’s Diary is that the character is supposed to be a bit on the frumpier and the “I don’t care if this fits, I’m going to wear it” side of fashion. Not being the best dresser, Jones goes on both sides of the spectrum.
Either she wears something that is way too tiny, or she goes and grabs one of her many oversized cardigans and pairs it with a horrid-looking undershirt and sweatpants. Sorry, Bridget, you might be a great character, but you need some help in the fashion department.
Juno MacGuff In Juno
Most teenagers go through experimental phases with their clothing. And no other character captures that weird time as perfectly as Juno MacGuff in Juno. She goes all in, wearing pleated mini skirts over baggy jeans paired with zip-up hoodies and thin fashion scarves that do pretty much everything but keep you warm.
While Juno is quite the character with her dry humor and quirky comebacks, it’s not enough to save her from joining other movie characters on the worst-dressed list.