Sex and the City was known for its amazing outfits as much as it was known for totally changing the game on the way dating on TV was shown. Carrie Bradshaw (Sarah Jessica Parker), Samantha Jones (Kim Catrall), Miranda Hobbes (Cynthia Nixon) and Charlotte York (Kristin Davis) definitely had some *aaaaamazing* looks, but they didn’t get it right all of the time. They made some questionable choices in the fashion department just like they did in the dating world.

While we’re fans of looking at our best Sex and the City outfit Pinterest boards on a regular basis for some lewk inspiration, it’s only right that we acknowledge some of the other more head-scratching looks. And hopefully, we will be able to learn something from them. Here are at 17 Sex and the City outfits that made us very confused.

1. Miranda’s Bucket Hat and Hood

There is no context needed for this outfit. The only place it would have possibly been appropriate is if Miranda decided to become a fisherman. And no SATC fan needs to watch the series to try and figure out whether that actually happened. It was actually worn to a picnic with the girls.
No, there was no torrential rain that day. Would it have been better if the bucket was under the hood? Or should we forget the idea of bucket hats and rain jackets together entirely? That’s for fans to start debating.

2. Carrie’s Red Blazer, Charlotte’s Jeans and Miranda’s Anorak

Normally, Sex and the City fans would eagerly await a scene with three or four of the characters because they knew the fashion was going to be through the roof. Unfortunately, this was not one of those occasions. Carrie’s normally on point mix-and-matching has left us confused thanks to that three-button jacket and cropped leggings. Charlotte’s classic style is veering towards frumpy given the shapeless coat and jeans. Miranda seems to be taking day-to-night dressing to the next level with the maxi skirt and anorak. And is everyone actually wearing sensible shoes? *Gasp*

3. Carrie’s Hot Pants and Samantha’s Striped Co-Ords

Ahhh, the rooftop party. The ladies were definitely in a party state of mind, but are greige hot pants the way to get into the party spirit? Carrie seems to think so. The look is almost there, but it’s one piece away from being SATC perfection. As for Samantha’s gingham co-ords, you’re on your own to figure the inspiration for this look. And those pigtails…

4. Carrie’s Head Scarf

There’s no denying that we love Carrie for her experimental style, but even she would probably admit that sometimes she pushed things too far and they ended up just being plain weird. And that’s how we got to this headscarf. Is it a headband, a sweatband, or is it just some clever hack to hide a pimple? And why-oh-why is it pointing up? Yes, it matches her pin, but beyond that? Hmmmm….

5. Samantha’s Mesh Dress and Bathing Suit

Remember when Samantha had that tantrum, meltdown, fit when she got thrown out of SoHo House’s pool? While the brief jaunt at the rooftop pool had plenty of opportunity for some fabulous swimwear, Samantha’s net-look wasn’t her usual power dressing.
Sure, she did have the supersized gold earrings, diva sunglasses, and a white swimsuit, but net anything is tricky to pull off. Remember, this wasn’t even a net top; it was a beach cover-up/dress.

6. Samantha’s Chambray Top Hat

When the ladies ventured outside the concrete jungle that was New York City, it was always interesting to see what they were going to wear. Sometimes it was fabulous, other times it was fierce, and sometimes it was a bit, erm… you know. That leads us to when Samantha ended up on a farm and thought that she would try and impress a farmer by milking a cow… while wearing a hot pink knotted blouse, coordinating pants and a printed chambray top hat of some sort. We won’t spoil the ending, but let’s just say a hat like that is best left off the farm and any city street.

7. Carrie’s Cowboy Hat and Bandeau Top

It takes a certain type of person to pull off a cowboy hat. And we’re not even sure that Carrie is that type of person. After all, she doesn’t work on a ranch. Therefore, she was already at a disadvantage with this red cowboy hat. Then you factor in the decision to pair it with a snakeskin bandeau top and a skirt that may or may not be a towel. Oh, and then there is that armband. Get the picture? Even at a beach party, it’s a difficult combination.

8. Carrie’s Plaid Coat

Admittedly, comfort isn’t one of the first words we would think of when describing Carrie’s style. In fact, it wouldn’t be one of the words we’d use to describe any of the characters on Sex and the City‘s style. That’s why it was a surprise to see Carrie rocking this oversized check coat. NGL, it looks like a bathrobe and not in the cool way trendy silk kimonos do. This is more of the fuzzy variety.

9. Carrie’s Knit Shorts and Long Coat

When you’re going out to pick up a baguette, what do you wear? When you’re Carrie Bradshaw, you apparently wear a strapless top with knit shorts, a long black trench coat, a newsboy cap and some printed designer heels. Scratching your head? Did you really think that Carrie would wear sweatpants and an old college tee to go on a bread run? Come on.

10. Carrie’s Bandanna and Gray Coat

One style lesson we’ve learned over time is that bandannas tied in hair like this are normally best left for days at camp when you’re making ceramics. You might have thought that Carrie could have given it a high fashion twist, but that’s not exactly true. The pink bandanna combined with the long gray coat and blue T-shirt has us scratching our heads. Does it make things better or worse if we tell you that Carrie is also sporting red pants?

11. Miranda’s Business Suit

Does your memory make you believe that Sex and the City was slaying it on the fashion front since the first episode? Well, this look of Miranda’s is from the premiere episode. You probably would have believed us if we told you it was from Season 26 given Miranda’s stuffy business suit and the safe striped shirt could be worn on by someone double Miranda’s age. At least she did try to jazz it up with the necklace, right?

12. Carrie’s Baby Blue and Red Outfit and Miranda’s Belt

Carrie gave us some unique color combinations that we wanted to try, but this baby blue and red one? Not so much. It doesn’t exactly help that we never figured out after all of these years whether that is meant to be a coat or a cardigan. Miranda’s also experimenting with red, but she kept things classic with beige, ruffled(?) pants. And then there is the matter of that belt… Or is it a sweater wrapped around her waist? Either way, it doesn’t look good.

13. Miranda’s Overalls and Puffer Jacket

No, you did not miss the episode where Miranda decided she wanted to quit being a lawyer and move to the mountains to cut down trees. This was actually during the first episode of season two. Miranda was walking down the street feeling good about having gained a perspective on men. Suddenly, she runs into an ex with his new GF. Her response? She runs away. It might have had to do with the emotional shock, but we’re sure it had something to do with those overalls, the puffy jacket, and the baseball cap.

14. Samantha’s Oversized Jacket

It’s always interesting to rewatch Sex and the City now to see how the styles have changed. Usually, it gets more interesting the further you go back in the season. While we came to love Samantha for her power dressing (and hilarious one-liners) this is one time when the girl boss look failed to translate as well as we hoped.
Even if this was a flashback scene to the 1980s, those shoulders would still be way too extreme.

15. Carrie and Miranda’s Supersized Hats

Despite the crazy circumference of this hat, Carrie is managing to pull it off with commendable aplomb thanks to the striped dress. On the other hand, Miranda has some issues with her sizable hat. Firstly, we should point out that Miranda was not 78 when this episode took place. She hasn’t even reached that age in any of the movie sequels of the series. The hat combined with the beige coat, sensible red top, and white gloves is something that would have been better suited to Miranda’s grandma or great aunt.

16. Carrie’s Bandanna and Tie-Dye Jeans

Remember what we said about the bandanna earlier? Exactly. Except this look might even be more confusing considering the multicolored top. Yes, we know that it’s Chanel but this goes to show you that not even a Chanel heart logo can save this print. And then we get to those pink and purple cropped jeans. There are almost no words except that this is something that some kooky drama teacher might wear at a posh creative arts school.

17. Carrie’s Fuzzy Lingerie

Okay, first let us say that Carrie wasn’t actually a fan of this look. In fact, she said, and we quote, “This screams hooker.” The outfits were pulled together by a stylist friend of Samantha’s for Carrie’s book cover shoot. When Carrie asked who in New York would ever wear something like this, Samantha responded, “I have one in red. Am I a hooker?” Awkward. Samantha might have been a fan, but we’re going to side with Carrie on this one.

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