Carrie’s ‘Bad’ Outfits on Sex and the City Were the Series at Its Best

Originally hailed as a feminist-seeming television anomaly in which four women leads all over 30 were allowed to fuck and say fuck freely, Sex and the City has since been subject to a near-constant discourse around its possible anti-feminism, definite Bush-era glamourization of the kind of craven consumerism that came disastrously crashing down in 2008, and the sort of rich white-lady kvetching that saw both its apex and its own demise with Lena Dunham’s Girls.

The conversation ultimately boils down to the sort of rhetorical question Carrie inevitably asks while smoking a cigarette in front of her open laptop in each episode’s second act: We couldn’t help but wonder, was Sex and the City ever any good? It certainly wasn’t a question that many of its die-hard, mostly young women audience asked out loud during the show’s original run. In his song “ ’03 Bonnie and Clyde,” even Jay Z admits that the only time he and Beyoncé “don’t speak is during Sex and the City/She gets Carrie fever.” And no matter how many of us, myself included, bitch about the fact that Carrie Bradshaw was a shitty friend who didn’t even bring cream cheese for the good bagels and a casually racist snob who referred to her ironic (and iconic) gold nameplate necklace as “ghetto,” it’s only in hindsight.

Carrie’s messiness, along with her charming mix of high fashion and complete chaos, was the appeal of the series, rather than an element we watched around to enjoy the redeeming qualities of an admittedly flawed show. And Carrie’s often mismatched designer outfits, artfully styled by Patricia Fields, encapsulate the debate around Sex and the City: Were they genius or tacky? Artifacts thrown together in discordant worship of pointless luxury or artistic commentary on the silliness of excess?

Nearly all of the outfits that are commonly understood to be Carrie’s borderline psychotic wardrobe fails come in instances where we most see her struggling with the bridge between who she is and who she’d like to be. The outfits, like the show rebooting nearly two and a half decades later, aren’t good or bad. They’re good and bad, just like Carrie and, ultimately, Sex and the City always were.

The show’s descent into complete wardrobe madness truly began with the duck purse. As Laia Garcia-Furtado, stylist and contributing editor at Vogue, points out, Carrie’s early-season outfits were relatively tame: “They seemed more believable in the sense that’s like, ok Carrie’s not rich but she splurges on things once in a while and mixes them with her own stuff and it was very natural,” Laia points out.

But in Season 2 Episode 10, Carrie’s sense of who she is collides with who her wealthy, emotionally withholding boyfriend Mr. Big wants her to be, with his gift of a $5,000 Judith Leiber rhinestone duck clutch. The bag, in Carrie’s estimation, demonstrates that Big wants her to be the kind of wealthy New Yorker who wears expensive shit correctly, while she wants to be the kind of New Yorker who wears expensive shit artistically. These two ideas clash when Carrie pairs the bag with a beautifully jumbled, mixed print Gautier tube dress at an elite party whose Park Avenue-type host insists everything in her life be clear or pristine white.

From there Carrie’s outfits as emotional barometer truly take off. The more streamlined and by-the-lookbook, the more Carrie is trying to get her shit together. The more incongruous (and ultimately divisive among fans), the more Carrie is spiraling. As the series reaches the conflict that will become its core—Carrie’s obsession with Big and determination to win Aiden to spite it, even if she’s only interested in their relationship when she’s on the cusp of destroying it—her outfits become the most reviled of the series: Her ill-advised cowboy hat ensemble to meet the 25-year-old Big leaves her for, the newsprint dress (that notoriously racist designer John Galliano said was inspired by the trash unhoused people use to stay warm) Carrie wore to apologize to said 25-year-old after fucking her husband, the backward Chanel blouse Carrie wears when she decides to simply embrace the fact that she’s emotionally stunted and dates a man-child.

The outfits I love and remember most are from Season 4, when Carrie, fresh off cheating with Big, is trying to convince herself she loves Aidan. These outfits are the ones most hated by other fans, fittingly, because this iteration of Carrie is her most exhausting and self-obsessed. It’s in Season 4 when Carrie wears the infamous belt around her bare waist just minutes before a wedding dress gives her hives, which Laia agrees is “genius.” It’s this season in which Carrie oddly pairs a newsboy cap and fanny pack with Prada’s bold striped skirt and crop top, a collection Laia calls one of their “all-time greatest” before admitting that “the hat and fanny pack are too much,” which “feels like Carrie.”

When Carrie is doing too much, chasing Aidan out to bars to prove (mostly to herself) she’s the cool girlfriend who won’t cheat again, she wears too much. Her clothes make no sense. My favorite outfit of the series comes later in the same episode, when Carrie pretends to give a shit about Aiden’s dog while wearing a ridiculous pantaloon zoot suit with what looks to be a 1940s child’s baseball uniform top, a 90-year-old man’s suspenders, white heels, and that same absurd newsie cap. Stylist Ashley Cortez calls the look “very dated,” because of the very early aughts length of the pants. But the look telegraphs the precipice of Carrie’s emotional tipping point and her forced realization that she’s not who she’s pretending she wants to be.

Throughout the entirety of Sex and the City, in every season, Carrie really sucks as a person at least once. But the ways in which she is terrible—because she lies to herself and through the lens of those lies makes awful choices—feels human in a way that the fabulous settings and million-dollar wardrobe budgets do not. When she wears her Prada and Chanel correctly, like the perfectly tailored suit she dons to get adorably drunk at Vogue and be harangued through no fault of her own, is when Carrie feels most flat, most boringly privileged, and most predictable. It’s when Carrie gets messy that the outfits, the character, and the series really come alive.