Carrie Bradshaw Outfits That Still Look Chic Today (And Those That Didn’t Age As Well)

Sex and the CityThe series became a cult classic as soon it aired in 1998. Its main character, Carrie Bradshaw, a fashion icon and writer from New York City, stunned audiences with her everyday couture looks. 

Her unique style was a mix of high-end designer pieces and funky silhouettes with a little creativity. Some looks have stood the test of time. Others? Other? 

Grab a cosmo and get comfy; we’re about to revisit some of Carrie Bradshaw’s absolute best (and worst) looks.

Still Chic: LBD and Aviator Combo

Carrie Bradshaw wearing her charcoal bodycon dress with aviator shades on Sex and the City.

Carrie’s season two out-to-lunch look is as timeless as it is chic. Her LBD—technically a flattering shade of charcoal—is a simple bodycon dress that blends casual, dressy, and trendy. 

Bradshaw let her accessories, and her hairstyle, do all the heavy lifting in this ensemble. The basic dress was completed with Bradshaw’s classic aviator shades, a gold necklace, and wavy golden locks. 

Of all of Bradshaw’s iconic looks, this is by far one of the most subdued. This makes her outfit as timeless in 1999 and 2021.

Trendy 20 years later: Chunky Sweater, Cropped Jeans

Carrie Bradshaw in a chunky brown and orange striped sweater, black cropped jeans, and snake print kitten heels on Sex and the City.

Despite airing nearly two decades ago, Bradshaw’s chunky sweater and cropped jeans combo is as stylish as ever. 

Paired with pointed-toe pumps and a cropped, curly ‘do, Bradshaw exudes effortless fashion in this casual look. Her jeans’ raw hem keeps her outfit casual without going full-comfy mode. 

Sarah Jessica Parker is stillBy the way, I love wearing cropped jeans. At only 5’3”, Parker uses tailored, cropped pants to elongate her petite legs. It’s a bonus to be able to show off some killer shoes.

Jaw Dropping, Always: Vivienne Westwood Bridal Gown

Carrie Bradshaw in her iconic Vivienne Westwood wedding gown on Sex and the City.

Technically, this outfit was in the 2008 Sex and the City Film, not TV series. You can’t blame me for including it on my best-of list.

Carrie’s jaw-dropping bridal look was a lush, multi-layered silk gown. Expertly structured and with a hint of sparkle, Bradshaw’s dress is what couture bridal dreams are made of. 

Carrie style, the look includes a bright topaz headpiece. The Vivienne Westwood gown was on display at the Film Festival a decade later. Westwood’s New York boutique.

A Forever Classic: Versace Tutu Dress

Carrie Bradshaw wearing a Versace tutu dress in Sex and the City’s series finale

Sex and the City’s opening credits cemented Carrie’s pink tutu and heels into the American pop culture lexicon. Even viewers who are not familiar with the series will recognize her distinctive outfit.

The series finale also features the following: SATCThe original look was a beautiful tribute by the design team. In an artful display of Carrie’s character development, she sports a tutu Versace dress in Paris. 

The muted green hue and tailored cream blazer work perfectly with Carrie’s dark, tousled curls. It’s the wearable, matured, classic version of the bubblegum pink ensemble we all came to know and love.

Please Never Again: The Belted Bare Waist

Carrie Bradshaw wearing a crop top, skirt, and belt around her waist.

Costume designer Patricia Field styled Parker’s character for 144 episodes of the series alone. Out of the hundreds of outfits she chose for Carrie, there’s only one she regrets. 

“I look at it and say, ‘eh,’” Field told Repeller. “She was wearing a skirt and crop top, and I threw a belt around her naked waist. Even when I did it, I was hesitant, but I think Sarah Jessica liked it, so I went ahead and kept it on.”

“But when I saw it later, I thought it was just obnoxious,” Field continues. Obnoxious? Maybe not. Perhaps it is better to keep the past. Perhaps so.

An Early Aughts Nightmare – Necktie and LBD, and Bra

Carrie Bradshaw wearing a slinky dress and necktie in the Sex and the City film
(Warner Bros.) (HBO)

Carrie’s slinky dress and necktie combo can only be described as a mid-aughts fever dream. The look was featured in the second Sex and the City Film, released in 2010. 

Is she trying to be Avril lavigne by wearing a necktie? Is the lacy bra peekaboo a tribute to Anna Nicole Smith? Parker can make a potato-sack look great, but this outfit looked like it was made for the kitchen sink. 

This outfit is a fitting example of chaotic mid-aughts fashion. It should be kept in 2010, however.

Still Confused: Bandana Dress and Hobo Shawl

Carrie Bradshaw wearing a multi-colored bandana dress and a mustard yellow shawl
(Warner Bros.) (HBO)

Our worst-of look is this mismatched and confusing summer ensemble. First, the multi-colored paisley shawl. Then there is the shawl with a holey, spicy brown mustard yellow. 

The final touch to the look is a straw cowboy head hat. Certainly not one of Bradshaw’s best, it looks like she threw the outfit together with things she found from a theatre’s green room. 

But hey, her zany fashion sense and extravagant lifestyle are why we’ve loved Carrie Bradshaw for so long. The long-awaited SATC follow-up, And Just Like That…Available on HBO Max now: 

The first episode aired December 9, 2021 and will continue through February 3, 20,22. And I can’t wait to see the couture, chaotic, and all-around iconic looks Bradshaw plans to serve for these ten episodes.

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