Top 10 Most Ridiculous Outfits on Sex and the City
#10: Pink ‘80s Prom Dress (with Headscarf!) “Coulda, Woulda, Shoulda”
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The word “wearable” cannot often be applied to outfits worn by Ms. Carrie Bradshaw. Well, if she were attending prom in the year 1987, then *maybe* this ruched pink number would work. But window shopping Hermès in New York City? In that case, we’d categorize it squarely in the NOT wearable category. But it’s not just the dress that makes this one of “Sex and the City”’s most ridiculous outfits: it’s the accessories, too. There’s the chunky gold necklace, the mismatched boutonniere, and we cannot forget about the Hermès headscarf. Plus, the irony of Carrie coveting a classic and classy-looking Birkin bag while dressed like this is not lost on us, either.
#9: Tie-Dyed Chanel “Hot Child in the City”
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One of the show’s funniest episodes also features one of the all-time worst outfits. Carrie is single late in season three and stumbles into a comic book store where she meets the owner, who is immediately interested in her. Surprisingly though, this meet cute takes place while she’s sporting a pretty atrocious tie dye ensemble with Chanel logos splashed all over it. Chanel is known for being the height of haute couture, and has a reputation for elegance and class, but this outfit is anything but. The sweater alone would have been one thing, but paired with those pants and that bandana, it’s a full on fashion nightmare.
#8: Beer Wench Look “The F*** Buddy”
Many of Carrie’s outfits verge into costume territory, but this one in particular really looks like she’s dressing up for a theme party rather than dressing for a day in the real world. She may have missed the memo that it wasn’t Oktoberfest when she put on this puffed sleeve blouse with a German-inspired top layer. As if the outfit wasn’t enough on its own, she also put her curly hair into pigtails, which made the final effect even more over-the-top. There were some truly awful outfits in the early seasons, and this has to be one of the absolute worst.
#7: Blue-Sequined Suit “Escape from New York”
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Near the end of season three, the girls need a change of pace so they leave New York to head for the west coast in an episode titled "Escape from New York", which takes place in Los Angeles. The show’s costume designers clearly had a field day with this opportunity, giving each of the ladies a new LA look that was a pretty big departure from their typical one. While there are some good outfits in this episode, Samantha’s fully sequined blue suit is a big miss. The matching scarf certainly doesn’t help either.
#6: Little Boy Outfit “Take Me Out to the Ballgame”
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Miranda doesn’t care about fashion nearly as much as her girlfriends do, typically wearing office-appropriate suits and dresses throughout the series. Because she’s not taking fashion risks, she doesn’t often have fashion fails, but when she does, oh boy are they good (or bad, rather). In the second season premiere, Miranda is annoyed that her friends only want to talk about men, and chooses an outfit that is about as unfeminine as you could imagine. The overalls, puffer coat and cap are in a similar hue, which looked ridiculous at the time, but somehow seems kind of in fashion now? Maybe she was just ahead of her time!
#5: Chanel Headscarf “I Love a Charade”
Throughout the series, Samantha’s fashion sense is pretty consistent. She likes to wear powerful outfits in bright colors that show off her inner confidence and creativity. She doesn’t often have fashion flops, but in the finale of season five, she wears an accessory that completely dominates her otherwise totally normal outfit. The item in question is a Chanel scarf, which should be a no-brainer for a classic couture look, but she styles it like a headscarf, which completely destroys the intended effect. It’s best to remember that a high fashion name brand can’t always save a bad sartorial decision.
#4: Belted Shirt, No Pants “Cock a Doodle Do!”
Like Chanel, Hermes is a deeply respected fashion brand that has been around for decades. But, it also can’t completely carry a bad outfit. In the season three episode “Cock a Doodle Do!", Carrie walks around her apartment in an oversized menswear button-down shirt and bare feet. Rather than keep this look cute and casual though, she decides to belt the shirt with a classic leather Hermes belt, which makes it look a little try-hard. If you’re trying to seem like you just threw on your boyfriend’s dress shirt, don’t add an accessory that ruins the effect.
#3: Carrie's Cowboy Outfit “Twenty-Something Girls vs. Thirty-Something Women”
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When Carrie runs into Big again after they break up in the show’s second season, she finds herself in a nightmare scenario when she’s at a theme party and is wearing a revealing Western ensemble. We get it, this outfit is supposed to be bad because Carrie has to feel extra embarrassed when she meets Big’s new girlfriend Natasha for the first time. But even that doesn’t excuse it. A tube top with a low slung skirt would be bad enough, but pairing it with a red cowboy hat was pretty bad even for a costume.
#2: Hat Over Hoodie “The F*** Buddy”
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In the very same scene where Carrie sports her beer wench ensemble in season two, Miranda manages to wear something even more ridiculous, which is quite the achievement. While they’re having a conversation in the park, Miranda is inexplicably wearing a sporty looking hoodie (with the hood up) and some sort of bucket hat on top. Did we mention she’s also wearing a turtleneck UNDER the hoodie? Wearing a hat on top of a hood is quite the move, and we’ve gotta say Miranda is not pulling this one off. Before we unveil our top pick, here are a few dishonorable mentions. Retro Ruffled Skirt “Out of the Frying Pan” Punk Rock Jumpsuit “The Post-It Always Sticks Twice” Gold-Accented Outfit “Catch-38” Cap & Menswear Tie “Baby, Talk Is Cheap”
#1: Bare Belly Belt “A Change of Dress”
Do pastel pink and green go together? Debatable. Not debatable? Belts belong over clothing, not bare skin. Carrie and a very pregnant Miranda are out for a walk and some impromptu wedding dress shopping. And, we’ll just say it: that poofy, dated wedding gown is not the worst thing Carrie wears in this scene. Miranda is her usual, tailored self in a classic trench and button-down combo, while Carrie… well, she’s wearing a crop-top blouse, a misplaced belt and a crown of thorns? As is the usual case for Carrie’s ensembles, none of these are trends we’ve seen before or since, and all together it’s a hot mess. We will say this though: SJP’s abs are TO DIE FOR.
