26 of Carrie Bradshaw's wildest and most questionable outfits on 'Sex and the City'

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Callie Ahlgrim,Erin McDowell
·6 min read
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carrie bradshaw opening sequence satc
"Sex and the City" costume designer Patricia Field bought Carrie's iconic tutu skirt for five dollars. HBO

When she paired an '80s prom dress with an Hermès headscarf.

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Why isn't the scarf folded properly? HBO

Many of Carrie's stylistic decisions involve questionable headgear, but this placement of a Hermès headscarf is one of her worst.

And then, never one for minimalism, Carrie threw in a random boutonniere and an impossibly ruched dress for good measure.

When she wore a newsboy cap and a two-tone knit romper.

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She accessorized with flowers and a baguette. HBO

Though it initially appears Carrie has donned short shorts and a tube top (underneath a long jacket worthy of "The Matrix"), the centerpiece of this bizarre outfit is actually a knit romper.

When she wore a belt around her bare waist.

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That belt isn't serving any purpose. HBO

Even without the belt, this lime-green-and-pale-pink outfit paired with a thistle headpiece is a lot to take in. Even the show's costume designer Patricia Field later admitted this outfit was a bit of a miss.

"The show ran for six years and there were about 24 episodes a season, so that's a lot of outfits, but I only have one where I look at it and say, 'Eh,'" Field told Repeller. "She was wearing a skirt and a crop top, and I threw a belt around her ... waist."

Even when I did it I was hesitant, but I think Sarah Jessica liked it, so I went ahead and kept it on," she continued. "But when I saw it later I thought it was just obnoxious. I should have slung the belt a little lower."

When her skirt included an inexplicable tail.

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It almost looks like a bunny tail. HBO

From the front, Carrie's button-down-and-skirt combo is simple and chic, but when she turns around, some kind of tail is revealed.

When she basically wore a bird on her head to get married.

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Her wedding dress was designed by Vivienne Westwood. Warner Bros.

Carrie's first wedding look was beautiful and elegant. But then she added blue bird feathers as an accessory to the side of her head, for some reason.

Even Bradshaw later admitted the choice may have been over the top, saying, "I put a bird on my head."

When she wore a newspaper as a dress.

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She can often be spotted wearing her "Carrie" necklace. HBO

While this Dior dress — which actually made two separate appearances in the show — is definitely classic Carrie, that doesn't make it any less strange.

When she wore a bandeau bra to "the event of the season" in the Hamptons.

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The girls attend a billionaire's yearly hoedown during a trip to the Hamptons. HBO

Considering the event was "a big hoedown full of cowboys and caviar," in Carrie's words, her hat is excusable. But why she decided to attend the party in a bandeau bra, long skirt, and rainbow armband is inexplicable.

When she wore this weirdly fancy hat on a casual date.

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It resembles hats worn by British guests to a royal wedding. HBO

In fact, Carrie's then-boyfriend Jack Berger poked fun at the accessory.

When she wore this unfortunate bucket hat.

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Unfortunate headgear is a theme in Carrie's life. HBO

The outfit also included a white tank top and blue-and-purple blazer.

When she wore a tie over her slinky black dress.

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Carrie wore this to celebrate her wedding anniversary in the second 'Sex and the City' film. Warner Bros.

The addition of the tie is simply baffling, especially considering she wore this outfit to eat dinner at home.

When she carried an umbrella when it wasn't raining.

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Otherwise, her blue knit dress is quite becoming. HBO

It was a sunny day, and yet Carrie apparently insisted on bringing an umbrella to complete her look.

When she wore knee-high rainbow socks.

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She donned a red slip dress to lounge in her own apartment. HBO

The socks were both loud and unnecessary.

When she layered cargo shorts over her bathing suit.

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Samantha helped her friends sneak into the pool at SoHo House. HBO

In another episode, she pairs men's board shorts with a bikini top.

When she wore a dress that resembles multiple bandanas stitched together.

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There's so much going on here. HBO

Carrie's multicolor dress is confusing enough on its own — but she took it to the next level with a cowboy hat and some kind of holey shawl.

When she wore a peasant top, athletic shorts, and red heels to secretly meet up with Mr. Big.

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Carrie threw this outfit on to meet Mr. Big. HBO

Despite obviously leaving the house in a hurry, not even that can excuse this odd look.

When she wore this pinstripe mess.

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Carrie is dedicated to her questionable hats. HBO

Only Carrie could pull off this attempt at business casual.

When she couldn't have possibly worn more pearls.

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This takes layering to new heights. HBO

You can also spot Carrie's first engagement ring hanging around her neck.

When she paired a Dior t-shirt with a massive skirt.

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Carrie wore this outfit to explore Abu Dhabi. Warner Bros.

The individual pieces of this outfit were probably not meant to go together.

When she paired purple sunglasses with a silk headscarf.

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She also went with heavy black eyeliner. HBO

This look would only be acceptable in a '90s music video.

When she couldn't get enough of stripes.

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Carrie wore this outfit for her first day living in Paris. HBO

This monochromatic look is made even more chaotic by the flat cap on top.

When her shirt looked like it had been shredded.

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Carrie wore this outfit in the first 'Sex and the City' movie. Warner Bros.

Clothing slits may be trendy, but perhaps not like this.

When it must have been laundry day.

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Carrie is wearing nearly every color of the rainbow. HBO

Not only did Carrie pair tie-dye leggings with a multicolor top, she topped off the look with a blue bandana and questionable earrings. However, the top was Chanel, so perhaps it isn't that bad.

When she put a cloud around her dress.

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The puffy addition seems inconvenient, at least. HBO

Carrie took the asymmetrical dress trend to the next level.

When, after falling into the Central Park lake with Mr. Big, Carrie appeared to don his white shirt and a Hermes belt to walk home in.

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Carrie's white men's shirt barely functioned as a dress. HBO

Despite barely skimming her thighs, this look is undeniably chic and sexy — though totally impractical for actually walking through the streets of New York City.

When she wore a visible lace black bra, khaki Bermuda shorts, a headscarf, and heels.

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Sarah Jessica Parker in "Sex and the City." Bill Davila/WireImage/Getty Images

Sarah Jessica Parker was pregnant with her first child while filming this scene, so we'll give this strange outfit a pass.

When she opted for this newsboy look to walk her boyfriend's dog.

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Carrie scrambled to grab Pete while wearing this over-the-top look. HBO

Only Carrie Bradshaw would wear a pinstripe suit with cropped pants, white heels, and a newsboy hat to do such a basic activity.

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