Carrie Bradshaw's Most Fashionable Moments

Carrie Bradshaw — the fictional character portrayed by Sarah Jessica Parker on the iconic HBO series Sex and the City — rewrote the rules of fashion. Not only did she put Manolo Blahnik on the map, but she also made tutus work in Times Square and had audiences coveting her closet and wardrobe (and rent-controlled apartment!). 

To celebrate the fashionable moments from the show, we sat down with its costume designers Patricia Field, Rebecca Weinberg, and Eric Daman, along with InStyle founding editor and former fashion director Hal Rubenstein, to compile a list of the TV star's greatest hits.

Keep scrolling for Carrie Bradshaw's best outfits throughout the series' six-season run and its two spin-off films.

Tutu and Tank

Field set the tone for Carrie's always-unexpected style when she opted for a "quirky" tutu and tank look for the series opening credits. 

"I remember I bought that tutu for $5!" said Weinberg in disbelief.

"Our seamstress had to duplicate it because we knew in the sequence it was going to get wet." 

We saw the famed tutu again in the first film when Carrie did a closet clean-out with the help of her best friends before she moved in with Big (Chris Noth). The girls' unanimous vote? A must-keep!

Pat Field's All-Time Favorite

Asked to identify her favorite piece, Field didn't hesitate to name the drop-dead gorgeous Versace gown Carrie wore while waiting (and waiting) for Petrovsky on her first night in Paris towards the end of season 6. 

"It took you out of reality," Field said.

Rubenstein agreed, "It's acres and acres of tulle and chiffon in this darkly romantic color — the perfect dress to be dumped in. There's nothing more woeful than seeing a beautiful woman all dressed up with nowhere to go."

The "He Loves Me, He Loves Me Not" Dress

"That was a moment in the show where it was like, it's happening, or it's not happening; he loves her, or he doesn't," Weinberg recalled of the time Carrie memorably fell into the lake with Big in season 3 wearing this Richard Tyler dress.

Weinberg said, "Richard made two of those dresses for us in less than two weeks' time!" 

Carrie paired it with a Louis Vuitton handbag and vintage shoes. 

"Those clear vintage shoes were so beautiful with little rhinestones pressed into the plastic, and that bag was a total church lady bag," she added.

The "Carrie" Necklace

"One day, my car broke down, so I had to take the train, and I saw all these great Italian girls with their nameplate necklaces," said Weinberg of the inspiration behind Carrie's iconic necklace. "For Christmas, I went down to Canal Street and made Pat one that said 'Patricia' that she just loved. So then I went down and made SJP's there too!"

Leave it to Carrie to pair such a downtown accessory with the most uptown of dresses. 

"I remember that beautiful vintage dress. It was from the '50s. I want to say it came from Twice in Miami," Weinberg recalled. "Pat and I would spend a lot of time in Miami. We'd get in her Oldsmobile and drive around to all our favorite vintage and thrift stores."

High and Low Mix

"This is a fun combination of high and low," said Rubenstein, referring to Carrie's season 5 ensemble, which included a sweater from mall staple Club Monaco, a dress by department store favorite Nanette Lepore, and a Chanel jacket. 

Weinberg gushed, "I love the color!"

Newsworthy Dress

Field didn't mind having Carrie revisit past favorites — like this John Galliano for Christian Dior newsprint dress, which she originally wore on season 3 when she apologized to Natasha for her affair with Big — in the movie. 

"There's a reason for it. She has an experience that merits re-wearing it," Field revealed. 

Fresh-Off-the-Runway Vest

By the time Carrie was preparing to marry Mr. Big in the first movie, she (and the SATC costume designers) had no trouble securing current styles, like this Proenza Schouler military vest and studded strappy sandals. 

"Everyone wanted their clothes on the show," Weinberg said. "Boxes and boxes would arrive daily."

Flower Power

"SJP was really into the flowers. One day, she said, 'Let's do a big flower.' They started small and got larger and larger, and then it escalated into a comedy of flowers," Weinberg told us. "This is Holly Golightly's black sheath and pearls. 

"It inspired real fashion to use flowers as accessories," added Rubenstein.

We loved the rest of the outfit, too — hello, Dior saddle bag! 

"This is a beautiful Americana-tailored look; it's very Grace Kelly. Those pants were half-lined to the knee — I think I borrowed them a few times," said Weinberg of the gorgeous Tuleh trousers from season 3.

Parisian Stripes

"There isn't anyone more synonymous with Paris than Sonia Rykiel. Carrie's in Paris, so she's wearing a classic Parisian knitwear designer," commented Rubenstein of Carrie's all-striped ensemble on season 6.

He added, "I wouldn't love this in N.Y.C., but it's so right for the scene. What could make more sense than being in 'the city of love' with your love, wearing things that are soft and romantic, and with an interpretation of her signature flower, of course!"

"Goodbye to Big" Louboutins

The ruffled, rose Louboutins that Carrie chose for her goodbye to Big at the end of season 4 were only one pair in a long line of truly stunning stilettos (good thing, too, as they were wrecked when Miranda's water broke all over them).

Carrie spent, by her own reckoning, tens of thousands of dollars on shoes over the course of the series, but Weinberg insisted that it was writer-director Michael Patrick King who turned many a shoe designer into a household name. 

"He was the one who said, 'Let's talk about Manolo,'" Weinberg shared.

"Around the Way" Look

"That's what Pat would call an 'around the way' look," Weinberg said of Carrie's kooky combination of tie-dye leggings, a bright blue kerchief, and a wildly patterned Chanel blouse. 

"She looks like a girl from the Bronx or Brooklyn," added Weinberg.

Rubenstein seemed equally amused by the outfit, although he disagreed about the provenance. 

"This is Carrie in cartoon land! But does it make me laugh? Of course," Rubenstein said. 

Daman, for his part, is still a fan, telling us, "This look still has edge and lots of MTV appeal."

Pat's Patchwork Coat

The colorful patchwork coat that Carrie wore to stalk Aidan (John Corbett) after Stanford spotted him in the Sunday Times on season 3 was actually one of Field's personal pieces, divulged Weinberg. 

"We just threw this together," she said of the outfit.

"It was one of those moments we didn't plan out." Rubenstein added, "This look is more Pat than Carrie. Pat was a pioneer downtown designer, and the streak of downtown club girl that runs through Carrie's wardrobe comes from Pat Field."

Not-So-Classic Nautical

Carrie and Samantha's (Kim Cattrall) coordinated sailor styles put both Field and Weinberg in mind of a classic 1960s girl group. 

"It's like they're the Supremes," said Field. 

Daman, too, looked fondly back at Carrie's "cool, contemporary, and casually chic" take on the nautical trend. 

"I love it for TV," said Rubenstein. 

Still, that doesn't mean he thinks that aspiring fashionistas should follow suit, saying, "I don't think anyone should dress like this."

Vintage Striped Suit

Carrie's cropped, striped vintage suit is "very Joe DiMaggio, 1939," according to Weinberg. It turns out that the inspiration for at least part of this season 4 ensemble was Weinberg herself.

"The newsboy hat was very much my look at the time," she said.

"Running Errands" Romper

Carrie was often ahead of her time: While this Claude Pierlot one-piece struck many fans as being a little too bare when Carrie wore it to the farmer's market on season 4, Daman was quick to point out that it was a prelude to the popularity of rompers.

"Carrie was one of the first to openly embrace them," Daman said.

Head Scarf and Prom Dress Combo

"Anytime she puts that [scarf] on her head, I kind of hold my breath," said Rubenstein.

And the Hermes scarf Carrie paired with a pink vintage prom dress is no exception.

"This is TV, not fashion," he added.

Weinberg seconded his opinion, telling InStyle, "This looks like something Katy Perry would wear to the Grammys. And those white Manolo pumps were like a Catholic schoolgirl gone bad."

Visible Bra

"This is not one of my shining moments," admitted Weinberg.

Peek-a-boo lace underthings were a Carrie staple, but the look — seen here on season 5 — didn't always work.

"I have a problem with the cropped pants and the major bra," said Rubenstein.

Nor did he welcome the return of the dreaded hair kerchief, saying, "It's so much cuter to show a little hair above the forehead. Then it looks like you're wearing a scarf."

The "Meet Carrie!" Outfit

"This is Carrie's 'How do you do?' moment," said Rubenstein of the demure Romeo Gigli dress Carrie wore at the beginning of season 1. 

"This show wouldn't have been a success if we didn't fall in love with Carrie," he added. 

As for Weinberg? "I think she looks like a candy striper," she said.

Entrance-Maker

Weinberg didn't recognize Carrie's season 1 mini-dress. 

"It's kind of generic, just a sexy, close-fitting dress. Was it spectacular? No, but you could put SJP in a pair of inside-out sweatpants and a pair of Manolo Blahniks, and she'd look good."

Rubenstein added, "This is how you dress to go to a club. There's a little bit of sparkle because the lighting is dim. Carrie wouldn't wear jeans to a club because she'd want to make an entrance."

Masterfully Mixed

"The mix of the heavy metal belt and the soft, floral print is so Carrie," said Daman of this colorful ensemble from season 2. 

"She changed fashion by showing you can belt almost anything, and her mixing of metals — the gold bag with the sterling belt — was very fashion forward."

The look also struck Rubenstein as directional, although in a slightly different way. 

"Carrie taught us that you don't go shopping in a T-shirt and a pair of jeans; you go shopping dressed as if you've already bought something," Rubenstein said.

Fendi Baguette

"This is the beginning of the Fendi metamorphosis, when every bag she carried was a Fendi. The store was really great to us at that time. They would just be like, 'Take whatever!'" recalled Weinberg. "Eventually, the Baguette became a status symbol; in that moment, we were literally creating around outfits around the Fendi bag."

"Cover-Up"

"Shazam! Who else could make a sequined caftan so sexy?" asked Daman of the sheer vintage tunic Carrie wore on a girls' weekend in Los Angeles on season 3. "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!"

Engagement Ring Necklace

On season 4, Carrie paired a classic white Badgley Mischka gown with her engagement ring (worn as a necklace, much to Aidan's dismay). 

"This look doesn't really characterize the beginning of Carrie. This is what she evolved to. It was a symbolic time," said Weinberg. 

Rubenstein added, "This is real New York sophistication. Every girl would love to be Audrey Hepburn for just one scene, and this is SJP's."

The Forgotten Top

"This is Roberto Cavalli. We had that top for years in our wardrobe; I think we bought it at a sample sale," revealed Weinberg. 

Fittingly, the plot followed their lead: Carrie stumbled upon the forgotten sweater while cleaning out her closet on season 4. 

"I didn't love this then, but I do love it now," Rubenstein admitted.

Statement-Making Coat

Regarding the nude Calvin Klein dress and colorful vintage coat Carrie wore on season 6, Weinberg said, "That's another one of those 'I threw it on' kind of looks, but she totally made it work!"

Indeed, fans everywhere took inspiration from Carrie's style. 

"This is the Carrie where you start taking notes," says Rubenstein. "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."

"Date with the Russian" Dress

"Late on season 6, Carrie fell in love with Petrovsky, the Russian artist who wanted her to live in Paris. All of a sudden, her world became about ballet, art, and once again, the clothes make a shift," said Rubenstein. Here, Carrie wears an Oscar de la Renta dress to the Met ... and McDonald's. 

"The clothes became more serious," Rubenstein added. 

Compromising Boots

Shopping in Paris, Carrie wore a pink Betsey Johnson bustier, Lanvin coat, and knee-high boots (which were to blame for a horrifying tumble in the exclusive Dior boutique). According to Weinberg, 

"The boots compromised the outfit's sophistication, and the bustier stood out. This all looks a little bit mismatched to me, which was obviously purposeful," Weinberg suggested.

Rubenstein agreed, saying, "Carrie never did anything accidentally — she knows exactly what she's doing!"

The Very Carrie Suit

"There's an exuberance here," noted Rubenstein, referring to the cream Ralph Lauren suit and pink button-down that Carrie wore in the first film. "She is so happy to be in New York City and in love with Big."

Westwood Wedding Dress

"Carrie was always the eclectic girl," Field told us. 

So when it came time for her to wed Big, she chose an anything-but-ordinary Vivienne Westwood gown. 

"Pat created the ultimate look for the ultimate day," said Rubenstein before adding, "I would never want to see anyone in real life wear that blue-green feather headdress on their veil, but if Carrie didn't have something so out of the ordinary, I would've been incredibly disappointed!"

Vintage Prints

"I do love labels, but I love all kinds of intelligent clothing," said Field, and her continual use of vintage in the first film proved it. Field must love intelligent accessories, too: She added an Eiffel Tower bag by Timmy Woods to the one-of-a-kind outfit, a subtle homage to the city that brought Big and Carrie together (again).

'80s-Inspired

"The '80s were always important to Pat," said Weinberg. "She came from the nightlife and club scene and has always been influenced by that." 

For Carrie, Field paired an edgy punk belt with a simple pink shift and pearls, masterfully mixing downtown cool with uptown chic. 

"Carrie had the ability to switch," said Weinberg. "That, to me, makes fashion."

Tutu No. 2

The purple ball gown skirt Carrie wore when she ran into Aidan in the second movie started its life as a slip. 

"It's actually an undergown, but it was so pretty. I was like, let's make this a skirt and put it with a T-shirt," Field revealed. "It had that same quirkiness as that short tutu from the series' intro scene."

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