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

Sex and the City became a cult favorite as soon as it aired in 1998. Its main character, NYC writer and fashion icon Carrie Bradshaw, wowed (and shocked) audiences with her everyday couture looks. 

Her unique style consisted of high-end designer pieces, funky silhouettes, and a dash of creative experimentation. Some looks withstood the test of time. Others? Not so much. 

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

(HBO)

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 hairstyle do the heavy lifting for this ensemble. Her classic aviator shades, gold necklace, and wavy, golden locks added all the bells and whistles to this basic dress. 

Of all of Bradshaw’s iconic looks, this is by far one of the most subdued. As a result, her outfit makes as much sense in 1999 as in 2021.

Stylish 20 Years Later: Chunky Sweater And 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.
(HBO)

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 still rocking cropped jeans, by the way. At only 5’3”, Parker uses tailored, cropped pants to elongate her petite legs. (Getting to show off killer shoes is a bonus, obviously).

Jaw Dropping, Always: Vivienne Westwood Bridal Gown

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

Technically, this outfit was featured in the 2008 Sex and the City film, not the TV series. However, can you blame me for including this one on the 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. 

In true Carrie fashion, the look also includes a vibrant topaz headpiece. A decade after the film was released, the Vivienne Westwood gown went on display at 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
(HBO)

Sex and the City’s opening credits cemented Carrie’s pink tutu and heels into the American pop culture lexicon. Even those far removed from the series can recognize her distinct outfit.

And in the series finale, the SATC design team paid a beautiful homage to that original look. 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: Belted Bare Waist

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

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. Better kept in the past? Maybe so.

An Early Aughts Nightmare: Necktie, 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. Granted, the look was featured in the second Sex and the City film, released in 2010. 

Is she trying to embody Avril Lavigne with the necktie? Is the lacy bra peekaboo an ode to the late Anna Nicole Smith? Parker can make a potato sack look flattering, but this outfit seemed to get the kitchen sink approach. 

While a fitting tableau of chaotic mid-aughts fashion, this outfit should probably stay in 2010 where it belongs.

Still Confusing: Bandana Dress And Hobo Shawl

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

Speaking of chaos, our worst-of look is this confusing, mismatched summer ensemble. First, there is the multi-colored hodgepodge of paisley bandanas. Then, there is the holey, spicy brown mustard yellow shawl. 

Finally, we have a straw cowboy hat to top off the look. 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…, is available on HBO Max now. 

The first episode aired on December 9, 2021, and will continue through February 3, 2022. 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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