Carrie Bradshaw: 10 Times We Adored Her Vogue Sense Of Style (And 10 Times We Didn’t)

Carrie Bradshaw, played by Sarah Jessica Parker, is one of the most stylish characters on TV and while her love life was a mess, she always looked great...at least most of the time. Many of Carrie's ensembles stood out because they were experimental and a little quirky--and always paired with a pair of expensive designer shoes. While some of her looks started major trends in the fashion world, some of them didn't exactly catch on--and it's easy to tell why. Patricia Field, Rebecca Weinberg, and Eric Daman were the Sex and the City costume designers and they were responsible for Carrie's greatest looks...and her biggest fails. While they are all proud of most of the looks they created, they can't help but feel ashamed about a few of these fashion flubs.

Patricia Field is known for being one of the quirkiest designers in the business and she was the perfect designer for Carrie because she wasn't afraid to make some daring sartorial choices. According to Field, "Style has become very important, the whole idea of style, what your personal style is. It's your identity." While some of Carrie's outfits may be downright awful, each look is apart of Carrie's complicated identity. Carrie didn't always make the best choices when it came to her love life but she always tried to look her best no matter what, and most of the time she totally did. Here are some of Carrie Bradshaw's most fashionable looks...and some of her biggest fashion fails.

20 Fashion Roadkill

This look isn't exactly Carrie's fault because she thought she was going to wear a blue sequinned dress by Dolce & Gabbana for a fashion show. Unfortunately they changed her outfit last minute, and she was forced to wear jewelled panties with a sapphire satin Dolce & Gabbana evening trench (complete with leopard print on the inside!).

The whole look is an absolute mess and Carrie personifies the outfit when she falls flat on her face while walking the runway in sky-high stilettos. As she was sprawled out on the catwalk, Heidi Klum stepped over her, making her "fashion roadkill". Still, Carrie managed to get to her feet and keep her head held high, which is something not many people could do while wearing that outfit. Even though this look is impractical, ugly, and unwearable, it's not the worst thing that Carrie ever put on. It gets a lot worse.

19 Boho/Cowgirl

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While Carrie's beach body is envious, her beach party outfit leaves a lot to be desired. The snakeskin bandeau, the wrap skirt, and the weird arm band/bracelet was already a strange choice, but the orange cowboy hat is what really makes this outfit so appalling. It's hard to tell exactly what kind of look she's going for, but it's fair to say that she didn't find it.

While it may just be a quirky ensemble to wear at a low-key party with your friends, it's definitely not the outfit that you want to be wearing when you bump into your ex-boyfriend (who you're still in love with) with his much-younger new girlfriend. This strange mix of boho meets cowgirl somehow works the beach party setting but only barely. Of course, SJP can pull off just about anything, but just because you can, doesn't mean you should.

18 The Purple Ball Gown

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Carrie wore this purple ballgown skirt when she ran into Aidan in Sex and the City 2, and it's a nice nod to the pink tutu from the intro of the TV show. However, the giant skirt paired with the t-shirt is just a little too much. Originally, it was an undergown, but in order to pay homage to the pink tutu, it was turned into a skirt.

According to Field, "It had that same quirkiness as that short tutu from the series’ intro scene.” It is definitely a quirky ensemble but it's not exactly something that you could wear while you're out and about. Some of Carrie's looks were just TV fashion and not exactly real life fashion. TV fashion is, often times, completely unwearable in real life but that's what makes it so fun. However, this look didn't exactly catch on.

17 Queen Of Tulle

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Carrie Bradshaw is the queen of tulle. Not everyone can pull off a tulle skirt but Carrie Bradshaw is not one of those people. The first time we see Carrie in the series, she is wearing a pink tulle tutu in the opening sequence, and she somehow manages to pull it off. Finally, in the last episode of the series, Carrie wears another tulle skirt in Paris as a nod to how the series began.

The mint tulle skirt with the white top, the white jacket, and the dainty clear heels is the perfect outfit for her to be wearing when she bumps into Big in Paris. The skirt is so light and magical, that it looks like something out of a fairytale. This makes it the perfect outfit to give her for her last episode. However, once Carrie gets back to the city, she is wearing her iconic fur coat, a bright pink scarf, and a skirt with tulle underneath.

16 Bubbly At Vogue

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Carrie may have worn a Vivienne Westwood dress on her wedding day but this little number is another piece by Vivienne Westwood that's not as appreciated (but a lot more practical) than the extravagant gown. Carrie wasn't generally one to wear business casual ensembles but she wore this pinstripe suit to her first meeting at Vogue where her article was picked apart by the editor, played by Candice Bergen. She then has a martini or three and gets "drunk at Vogue" and no one has ever looked more stylish while getting day-drunk.

Carrie managed to make this gorgeous suit her own by embellishing it with a brooch and her nameplate necklace. Carrie was always able to put her own spin on anything she wore and we love her for that. There is nothing more appropriate for a meeting at Vogue than this ensemble.

15 All Dressed Up With Nowhere To Go

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This is Patricia Field's favorite piece from the entire show and it's easy to see why. The Versace gown with acres of tulle and chiffon was the perfect dress for Carrie's first night in Paris--of course, she ends up waiting and waiting for Petrovsky for hours until her whole night is ruined. This is the perfect dress for a night in Paris. It is so extravagant and romantic that it breaks your heart to see a woman in it who has nowhere to go. It's the kind of dress that begs to be seen.

This fairy tale gown retailed for $79,000 and actually had to be flown to Paris for this particular scene. Of all of Carrie's outfits, this was the most expensive one she wore on the show. It was only beaten by the $198,200 Solange Azagury-Partridge gemstone necklace that she wears in Sex and the City 2.

14 Carrie's Lizzie McGuire Style

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Honestly, this outfit looks like something that a Mary Kate and Ashley Olsen-loving pre-teen would have worn in the early 2000s, not something that a grown woman would wear in Manhattan. The pink cropped sweater buttoned up over a billowy white shirt/dress over a pair of baggy gray jeans is just not a good look--not to mention that hair!

Season 5 was a tragic time when Carrie started changing up her famous curls, and most of the hairstyles she tried out didn't work for her--especially when she straightened her hair. Straight hair was a big trend in the early 2000s so it's easy to see why she'd want to make a change but her wildly curly hair just works for her. While many of Carrie's looks are still chic almost twenty years later, this outfit should be left in 2003 where it belongs.

13 A Work Of Art

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Who can forget the gorgeous Richard Tyler dress that Carrie wore when she went to meet Big before falling into the lake? This dress from Richard Tyler's 'Resort 2001' collection is so delicately effortless and it fits Carrie like it was made specifically for her. It's the perfect dress for a romantic rendezvous.

The dress was paired with a simple pink Louis Vuitton handbag and clear vintage shoes with rhinestones. These accessories work so well in this ensemble because they don't steal the spotlight from the dress. Instead, they compliment it. After all, this dress deserves its chance in the spotlight. Two identical dresses were used on the show, one was sold for charity in 2001 and the other was given to Sarah Jessica Parker who later donated it to the Museums Victoria in Australia where it is currently on display.

12 A Comedy Of Flowers

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Sometimes Carrie went a little overboard with the flowers. According to Weinberg, Sarah Jessica Parker really loves flowers and one day, she just said "Let's do a big flower." You can't say no to SJP! Apparently, the flowers started out small and then got bigger and bigger until it "escalated into a comedy of flowers." Sure, it's comical, but we're more frightened than amused with some of the outfits.

While Carrie's love of flower accessories are a little too much for the general public, it did cause the fashion industry to take notice and start using flowers as accessories. In fact, Moschino's Spring 2018 collection was almost entirely dresses that resembled floral bouquets which stemmed (pun intended) from this trend that was made popular, in part, by Sex and the City.

11 The Don't-Rag

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Even Weinberg admitted that this outfit was not one of her "shining moments" and it's easy to see why. While Carrie was no stranger to a visible bra, this look isn't her best. There is so much going on with this outfit that it's hard to focus on just one thing. The cropped pants, the black heels, the colorful do-rag, and a sheer white shopping bag for a shirt--it's all too much. Of course, Carrie looks as confident as ever in this terrible outfit and she almost pulls it off. Almost.

The biggest problem with this outfit is that it's disorienting. When it comes to a visible bra, you need to make sure that it's the most eye-popping part of the look so that it doesn't get lost in the ensemble. Carrie always liked to take risks when it came to fashion but this one doesn't work out for her.

10 The Sequined Caftan

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When the girls go to Los Angeles in season 3, they shed their NYC sartorial sensibilities and opted for some very LA ensembles--but Carrie outdoes them all. Samantha is wearing a sheer top over a bikini, and red and black flared pants, but somehow Carrie still managed to wear something even more daring. There are few people in the world who can pull off a sheer sequinned caftan, and Carrie Bradshaw is one of those people.

According to Daman, "The elegance and simplicity of her black bikini with the flash and sheer dash of the cover-up are a perfect demonstration of Carrie's take on fabulous—a timeless mix of class and sass!” It was impossible for Carrie to go anywhere without making a big, fabulous statement and there's no better way to do that than with a shimmery sequinned caftan.

9 The Worst Of The Worst

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This is, quite possibly, the worst outfit that Carrie ever threw together. While taking a trip to the farmer's market in season 4, Carrie wore a Claude Pierlot romper with a black trench coat, a cabbie hat, and some slingbacks for good measure. Why? We have no idea. Carrie looks as confused as we are. This whole ensemble doesn't exactly fit Carrie's usual look, but maybe she was just experimenting with something a little different for a day of running errands. We've all been there, haven't we?

According to Weinberg, "Rompers are currently one of the biggest trends going, and Carrie was one of the first to openly embrace them." By itself, the romper is a cute look for Carrie, but paired with the smorgasbord of other items, it looks like a big mess. However, you have to admit that her legs look amazing in this outfit. That's gotta count for something, right?

8 Fashion Statement

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This look is so simple but so stylish and Carrie pulls it off so well. While her chic Calvin Klein dress is simple, by adding a colorful vintage coat, Carrie brought a pop of color to her ensemble. According to Weinberg, a coat is much more than a coat when it comes to New York City: “In other cities a coat is just used for warmth, but in N.Y.C. we see your outerwear, so your outerwear really needs to make a statement.”

If there was one thing that Carrie was always able to do, it was make a statement. Even if she was wearing the most drab outfit imaginable, she could always manage to add a bit of color or eccentricity. Even if her ensemble was a bit over-the-top, she could always pull it off. Pulling off a Carrie Bradshaw is easy when you have her confidence.

7 Take Me Out To The Ballgame

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Carrie, Miranda, Samantha, and Charlotte never went anywhere without looking their absolute best. Even when they go to a baseball game, their whole squad was on point. Honestly, is there anything more iconic than Carrie's baseball game look? This is exactly the sort of thing that you wear to a Yankees game in the afternoon with your girlfriends after you broke up with your boyfriend. The big fur coat over the sophisticated yet simple black dress with the floral pattern, brown heels, and gold aviators is such a look and it's peak Carrie Bradshaw fashion.

This look is so chic that she ends up catching the eye of one of the players which is exactly the kind of confidence booster any girl needs after a messy breakup. Even Carrie's most casual, laid-back ensembles are totally breathtaking and that is something that we should all aspire to.

6 The Prom Dress

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With this questionable ensemble, Carrie looks like she's about 15 years late to prom, and Weinberg describes it as "something Katy Perry would wear to the Grammys." The combination of the Hermes scarf wrapped around her head, the pink vintage prom dress, the chunky gold necklace, and the white Manolos, it looks like Carrie didn't even bother with a mirror.

It's hard to believe that someone as stylish as Carrie would ever dare to wear this ensemble in public (even Samantha looks embarrassed to be seen with her) but she looks as confident as ever. We should all aspire to have the same level of confidence that Carrie has while wearing this outfit.

5 Pink Louboutins

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Who could forget the episode at the end of season 4 where Carrie picked out her Christian Louboutin Petal Sandals to say goodbye to Big? It's definitely one of her most memorable looks. Of course, if you remember the heart wrenching episode you'll also remember that Miranda's water broke all over them! There is nothing more heartbreaking than a pair of ruined Louboutins.

This ensemble perfectly encapsulates the Carrie we know and love: the lacy black slip dress, the colorful coat with gold detail, ruffled pink Louboutins, and, of course, the name-plate necklace. This is peak Carrie fashion. Carrie said herself that she has spent thousands of dollars on shoes in her life (those Louboutin's retailed for $995) and that's something that's easy to do when you insist on only wearing shoes from the biggest designers. In fact, it was Carrie's love of Manolo's that helped Manolo Blahnik become a household name.

4 Your Girl Is Lovely, Hubbell

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If you don't tear up during the scene where Carrie quotes The Way We Were while saying goodbye to Big in season 3, are you even a Sex and the City fan? When Carrie met Big after his engagement party, she wore a gorgeous low-cut white dress with clear sandals and a dainty black handbag--it's so simple and still somehow so Carrie.

The ensemble is chic and elegant, and this is the perfect dress to say goodbye to the love of your life. This is the moment when she says, "You're girl is lovely, Hubbell," just like Barbara Streisand says to Robert Redford in The Way We Were. Cue the tears! Carrie rocked this look even though she once said that she "will never be the woman with the perfect hair, who can wear white and not spill on it." Turns out we can always surprise ourselves.

3 Stars And Stripes

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Let's be honest, Carrie always looked good in a crop top because of her killer abs. However, some of her ab-revealing ensembles don't stand the test of time. This outfit is almost a hit with the long sleeved black crop top and the dainty necklace but the red and white striped skirt, and the Gucci fanny pack is too over-the-top to be chic.

The red and white strips make her look like she's wearing an American flag, and that's definitely not a good look. If she was wearing a more subtle skirt, we could probably forgive her, but it's hard to look past the gaudy skirt paired with such a lovely little Gucci bag. Seriously, the only way you can make a Gucci bag look bad is if you wear it with a skirt like that. But, hey, with abs like that, no one is paying attention to the skirt!

2 Around The Way Girl

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When it comes to Carrie's worst fashion faux pas, this outfit almost always makes the list. With the strange combination of tie-dye leggings, a bright blue kerchief, and a Chanel blouse with a kooky pattern, she looks like she just threw together whatever articles of clothing she could find to create this monstrosity. According to Weinberg, this is what Field would call an "around the way" look; referenced in an LL Cool J song in which he describes a girl with hair extensions, bamboo earrings and "A fendi bag and a bad attitude."

While Carrie didn't always have a bad attitude, she almost always had a Fendi bag over her shoulder. However, LL Cool J would probably look at this outfit and laugh. When you're putting an outfit together, it's best to just stick with one pattern or else you'll end up with something so busy that you'll disorient an innocent passerby.

1 Classic Carrie

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This is one of Carrie's best looks because it's so simple yet so chic. The skin-tight slate gray dress perfectly fits her slim figure and the brown sandals are a perfect addition to the outfit--and let's not forget the classic gold aviators. Carrie wore this outfit in the episode where she dates the writer who has some trouble in bed and she eventually realizes she's only interested in him for his amazing family. She dumps the writer and puts on this classic yet sexy look and meets up with her girlfriends.

Classic Carrie. In the beginning of the series, she wears countless dresses like this one and it helped to solidify her as the sartorial icon she is known as today. While we love her eccentric ensembles, we will always love the classic Carrie looks that are always as chic as they are simple.

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