I spent the past week pouring through photos of Anna Wintour from the ‘80s and ‘90s, which led me to a very important conspiracy theory that I can’t stop thinking about. Have I built up enough suspense? Okay here it is: I’m pretty sure Anna Wintour’s pre-millennium outfits were the inspiration for Carrie Bradshaw’s wardrobe in Sex and the City.
Comparing these two women is interesting. Though I realize one is fictional, they are both ascribed an almost mythical authority when it comes to style — and they, in turn, have a relationship with style that borders on reverence.
“Fearless” and “timeless” are two adjectives frequently used to describe Carrie Bradshaw’s style, which is interesting because those characteristics rarely coexist in fashion. You’re either experimental or classic, but Carrie (a.k.a. legendary SATC stylist Patricia Field) merged them and somehow replicated that formula again and again. ’80s to ’90s Anna was no different. Her style was “of the time” while also being utterly apart from it: sequin mini dresses, statement blazers, enormous fur coats, silk slips and pops of color administered in generous doses, the entirety of which was also subsequently on display in Carrie’s laughably large walk-in closet.
I could easily copy and paste these outfits into 2017 and they would resonate just as acutely, perhaps because of their mutual aversion to overt trendiness. “Trends is a dirty word,” Anna once said to Tim Blanks. I can just as easily picture Carrie’s infamous voiceover saying the same: “I couldn’t help but wonder, is ‘trends’ a dirty word?” (She would likely tie this philosophy to shoes, dating, Magnolia cupcakes and Miranda’s hair in the same breath.)
Both Anna and Carrie exhibit a flagrant, almost joyful disregard for the notion that an interest in fashion should in any way minimize your intellect or undermine your authority. Anna said as much plainly when she wrote in Vogue about Hillary Clinton turning down a cover shoot: “The notion that a contemporary woman must look mannish in order to be taken seriously as a seeker of power is frankly dismaying.” (I don’t think she means “mannish” in the literal sense, but more so as a catch-all, stereotyped characterization for deliberately demonstrating a lack of interest in fashion).
Anna took over as editor in chief of Vogue in 1988, which means all of the photos included in this story were taken during her early years at its helm. While she proceeded to cement her jurisdiction as arguably the most important figure in the fashion industry, she dressed herself in technicolor dream minis, prints worthy of a chic grandmother’s living-room wallpaper, neon shifts, Barbie-pink suits and necklines that were decidedly, for lack of a better word, sexy. She was a walking testament to the fact that you can have fun with fashion and still demand to be taken seriously.
Ditto for Carrie. Granted, she isn’t the editor of Vogue, but she is a complex human woman with ideas and thoughts and a career and a life, a woman who is so much more than the outfits she unapologetically enjoys putting together.
She defends her right to do so, too: in a Season 6 scene when her short-lived boyfriend Jack Berger makes fun of her hat in the middle of a fight, she retorts, “It’s fabulous and you just said that to hurt my feelings. FAB-U-LOUS.” She takes the hat off, though, which always needles my empathy to watch, knowing full well what it’s like to be made to feel small for loving something often deemed superficial.
Don’t worry, I haven’t forgotten the tweed elephant in the room. I can’t write about Anna Wintour’s wild ’80s to ‘90s style without acknowledging the fact that it ultimately evolved into something less experimental. The Anna Wintour of today is noticeably more consistent with what she wears than the Anna Wintour of yore. She has a go-to uniform: black sunglasses + a dress that hits at mid-shin + a coordinating sweater or tweed jacket. Plus a long coat with a fur collar if it’s cold.
So what gives? What happened to the neon and the sequins and the athleisure? Why did she stop experimenting and start relying on a formula? If I had to guess, she finally hit upon the precise combination of clothing that makes her feel like the best version of herself. There is pleasure to be had in the process of uncovering that template (I’m certainly not ready to stop yet), but there is also something equally wonderful about recognizing that someone has found it. I can’t help but wonder (sorry — had to), if we ever had the chance to watch Carrie grow past middle age, might she make the same discovery? I’m personally rooting for the naked dress.
Photos via Getty Images.