As teenagers in California who dreamed of moving to New York City, Chelsea Fairless and Lauren Garroni grew up watching Sex and the City. Even the show’s key art looked appealing: “Sarah Jessica Parker sitting naked against the New York City skyline with a laptop strategically covering her,” remembers Fairless, who began watching the HBO comedy when it debuted in 1998, when she was around 14 years old. “My parents were totally fine with me watching Sex and the City as a teenager,” says Garroni, who was 13 when she first watched. “But they wouldn’t let me watch The Sopranos.” 

Like Carrie, Miranda, Charlotte, and Samantha, Fairless and Garroni both eventually ended up in New York City. They met at Parsons School of Design, though their mutual obsession with the series isn’t what brought them together: “Until the day we started the Instagram account,” says Garroni, “we don’t think we ever had a conversation about Sex and the City.” 

As Fairless jokes, they’ve certainly “made up for lost time.” Their account, @everyoutfitonsatc, is an obsessive catalog of Sex and the City’s style; since launching in 2016, it’s drawn more than 730,000 followers. Fairless and Garroni have also collaborated on We Should All Be Mirandas—a book filled with “life lessons from Sex and the City’s most underrated character”—and the definitive Sex and the City podcast Every Outfit, which goes beyond SATC to dissect everything from the Met Gala to the Kardashians. 

In honor of Sex and the City’s 25th anniversary this spring, Fairless and Garroni spent an episode of Every Outfit looking back at the show’s pilot, which aired on June 6, 1998. Afterward, the pair called VF over Zoom from their homes in Los Angeles to discuss Carrie Bradshaw’s introduction, the show’s warped version of reality, and where they’d like to see Carrie and company go in the upcoming second season of HBO’s Sex and the City sequel series, And Just Like That. 

Vanity Fair: I always forget how different the Sex and the City pilot is from the rest of the series. 

Chelsea Fairless: It is a weird vibe. At that point they hadn’t really figured out what the show was going to be. The first episode was literally adapted from Candace Bushnell’s column. 

Lauren Garroni: Sarah Jessica Parker herself has told a story that she forgot that she shot the pilot. That’s how…I won’t say insignificant. I won’t put words in her mouth. But [it shows] the lack of expectation she even had for the show.

It’s crazy to think that Sarah Jessica Parker, who is so intertwined with the character Carrie Bradshaw, almost didn’t take the role.

Garroni: She just had it. I really can’t imagine what other actress of that time would play the role. She was synonymous with New York.

A lot of women moved to New York because of Sex and the City. Which is funny because, looking back at the pilot, Carrie is kind of saying that New York is not what it used to be. 

Garroni: That is a symptom of every generation that moves to New York. There’s the older generation that’s like, “You missed it.” I never thought that I would get to say that, but going back now, I’m like, “Oh, you guys missed it.” 

Fairless: The pilot, specifically, does feel a lot darker. Even Carrie’s extremely messy, fucked-up apartment. It almost feels like a film noir when she’s standing on the rainy street corner. It’s really not giving a glamorous side of New York. 

Garroni: The introduction of Carrie does make her seem like the Philip Marlowe of heterosexual relationships or something, when she refers to herself as a sexual anthropologist. 

And you only ever see the back of Carrie’s head chain-smoking. 

Garroni: I could have sworn that she was going to turn to the camera and be like, “And that’s dating.” That would be the first moment to talk to the camera naturally. What a great introduction: “You thought you were following this chick? Guess what? It’s me, Carrie Bradshaw.”

The reviews make it seem like it was well received by critics. The New York Times called it “fresh and funny.” What were audiences thinking about the show when it premiered? 

Fairless: It was coming into a landscape of television which was not good. We forget Sex and the City was the first major TV show that HBO did. It came out before The Sopranos. So even Sex and the City at its worst is probably a lot better than what was on network television at that time.

Garroni: In our 10,000 hours we’ve done of Sex and the City, I think that’s something that gets lost. It was really Sex and the City that broke through before The Sopranos. 

You guys recently spoke to Candace Bushnell, who wrote the column that inspired the series and whom Carrie Bradshaw is based on. What were her first impressions of the show? 

Fairless: She is a big fan of the first season because it’s much closer to her column. I think that she really likes the show that they initially tried to make. Which is not to say she didn’t like where it went, but it was just closer to her idea of what it would be.

Garroni: [Creator] Darren [Star] sought out Candace, and she was a little surprised because her column was for people in New York. The book itself was a kind of cult-niche piece of media. He was really burnt out from network television and actively wanted to do something very gritty. 

Does the show resonate with you differently now, rewatching it as women who are closer in age to the characters?

Fairless: You really, truly understand the extent of these women’s struggles once you’ve actually been in the trenches. 

Garroni: The show gave us the impression that you would just go to the bank and have a date on Friday night, and you just sort of run into people. 

Fairless: On the other hand, once you live in New York, you realize a lot of this is extremely accurate. You can have the Sex and the City experience. There are fabulous parties every single night in New York.

How do you reconcile the things that haven’t aged well?

Fairless: One thing that people often forget when we talk about problematic aspects of shows from the past is that it was made for a problematic audience. That was reflective of the beliefs of most people that watched it. Watching Sex and the City now, I’m glad that there’s been social progress, right? 

Garroni: In a bizarre way, the reason that the show feels problematic is because it did push the needle forward.

What about elements that have held up?

Garroni: Unfortunately, I think being single in a metropolitan city and heterosexual men being trash is just an evergreen topic.

One of the major criticisms of And Just Like That is that the women are repeatedly made to atone for the sins of the series’ past. What are your thoughts on AJLT? 

Garroni: It was a massive overcorrection. You just sort of crash-landed into this new show, which is not called Sex and the City—it’s called And Just Like That. So Michael Patrick King was definitely signaling this is a different show. 

There’s no other example of women of that age working on a television series, being paid what they’re worth. So from that perspective, it’s a very exciting show.

If it were up to you two, what would happen in this upcoming season of And Just Like That?

Fairless: We would like Charlotte to have a plotline that isn’t about being a wife or a mother. We need Miranda to be broken up with Che, so she can figure out how to date as a queer woman. Carrie needs to be getting back to being fun again. 

Garroni: Carrie’s next book [would be] this almost High Fidelity–esque charting of her past relationships so that you could bring back all of her exes.

Fairless: Candace Bushnell is working on her memoirs. So that’s true to life in a sense.

Where does Aidan fit into all of this? 

Fairless: I don’t want it. 

Garroni: If this is a new show, why not give Carrie a new boyfriend? Jon Hamm! There’s a whole plethora of men who are in their 50s and 60s, who are hot, that could be Carrie’s boyfriend. 

If we are taking this Aidan plotline at face value, I think they make a lot of sense now. For Carrie, Big was her Everest, and she climbed that mountain and lived a life with him. Aidan wanted a family and wanted that traditional life, and somehow that has come to an end. 

Fairles: But he has kids now—he’s not going to try to rope Carrie into that. 

Garroni: I think Carrie has really great stepmom energy.