Every Outfit – Episode 237: On Taylor’s Engagement, Celesbians, SSENSE Drama

Hosts: Chelsea Fairless & Lauren Garroni
Date: September 5, 2025

Episode Overview

In a characteristically witty and fashion-obsessed installment, Chelsea and Lauren tackle the latest in pop culture, fashion, and queer internet drama. Highlights include Taylor Swift's engagement announcement (and the Gaylor fandom’s reactions), a packed celesbian news cycle (notably Chloe Grace Moretz’s wedding and high-profile lesbian lawsuits), the fate of retail giant SSENSE, major fashion campaign castings, and the ever-accelerating encroachment of AI into the fashion industry.

Key Discussion Points

Catching Up: Jury Duty, Fashion Fails, Mahogany Screening

• [00:54 – 04:38]
  • Chelsea and Lauren recount travel hassles, fashion disasters (greasy dress stains, baby-induced outfit changes), and their event at the Friend of the Fest festival.
  • Lauren: “Morty lost his mind at bedtime... he then proceeded to all over the outfit that you had selected for me.” - [02:13]
  • Chelsea laments slipping and falling at Figaro Bistro, resulting in a “fashion roadkill moment.”
  • Both reflect on wardrobe mishaps: “I just love that both of our outfits got fucked up.” – Chelsea [04:38]

Jury Duty Antics & Cardi B’s Court Case

• [04:43 – 09:21]
  • Lauren’s (failed) attempts to avoid federal jury duty: being a podcaster proved more effective than being a new mom.
  • They discuss the recent Cardi B trial, debunking rumors and recapping the outcome: “This was to teach people a lesson,” Chelsea [08:43]

Pop Culture Grab Bag: Powerball, Burning Man, and More

• [09:21 – 14:59]
  • Chelsea admits to Powerball fever and purchasing tickets with “no strategy.”
  • Burning Man recap: from a rare murder to a surprise childbirth (“cryptic pregnancy”).
  • Lauren: “It was a cryptic pregnancy. She didn’t know she was pregnant till she gave birth on the Playa.” [14:19]

Taylor Swift Engagement Frenzy & Gaylor Meltdown

• [14:59 – 21:27]
  • Chelsea’s emotional reaction and surprise at Taylor Swift and Travis Kelce's engagement (“I am really happy for her. ...I was starting to think this was never going to happen for her, honestly.” – Chelsea [14:59])
  • Speculation about Ralph Lauren wedding spawn, ring details, and wedding dress designer.
  • The inevitable reckoning within the “Gaylor” (queer Taylor Swift) fandom.
    • Quote from subreddit: “Sometimes I wonder, what if they actually get married? What if she’s really not queer at all?... I honestly think I could end up in the hospital or worse.” – Read by Lauren [19:41]
  • Karlie Kloss (alleged ex/muse) likes the engagement post.

Celesbian News: Weddings & High-Profile Lesbian Drama

• [23:20 – 34:24]
  • Chloe Grace Moretz and Kate Harrison’s Vogue-covered femme-femme Louis Vuitton wedding.
    • Chelsea: “She wore a light blue gown... two white wedding gowns, that’s a lot. It’s a weird vibe.” [23:53]
  • Discussing celesbian wedding aesthetics and after-party fashion misfires.
  • The lawsuit drama between RHONY’s Raquel Chavarmont and artist Mickalene Thomas: allegations of exploitation and sexual harassment.
  • The ever-unfolding saga of Elizabeth Gilbert (“Eat Pray Love”) and her upcoming lesbian memoir—scandalous excerpts abound.
    • Chelsea: “She’s such a fucking junkie. I’ll just kind of like… have her get her pills mixed up.” [29:27]
    • Lauren: “It is becoming abundantly clear that Elizabeth Gilbert is the definition of a woman that would do something for the plot.” [30:10]
  • Speculating on adaptation: “I hope it’s Julia Roberts again. Or... Cate Blanchett shaving her head.” – Chelsea [34:30]

Fashion News & Campaigns: Sapphic YSL, Miley for Margiela, and More

• [35:15 – 44:52]
  • Chloe Sevigny & Kate Moss’s YSL campaign: “one of the great homoerotic fashion advertisements in recent years.” – Chelsea [35:15]
  • New Margiela ambassador Miley Cyrus, a curious choice given the brand’s legacy of anonymity.
    • “It made me want to cry, actually, when I first saw this. Or, like, throw my phone into the ocean a la Carrie Bradshaw.” – Chelsea [39:53]

Venice Film Festival Fashion

• [44:52 – 51:47]
  • Chloe Sevigny, Charlotte Rampling, Julia Roberts, Amanda Seyfried, Greta Lee, Mia Goth, and Tilda Swinton among notable looks.
  • Julia and Amanda’s matching (very un-Versace) dark wash jeans from Dario Vitale’s debut; a “Sisterhood of the Traveling Pants” moment orchestrated by a shared stylist.
  • Mourning the death of Giorgio Armani, who “was working up until his death.” [52:08]

Industry Shifts: Editorial Shakeup, E-Commerce Woes & AI Slop

• [55:13 – 69:02]
  • Chloe Malle named Head of Editorial Content at Vogue, replacing the title Editor in Chief but not Anna Wintour herself.
    • “Chloe Malle has a journalism background, which is something that Anna Wintour highlighted when she talked about appointing her.” – Lauren [58:20]
  • SSENSE seeks bankruptcy protection; reflections on flash sales, young designers’ struggles, and the legacy of now-failing retailers.
  • J. Crew’s AI-generated campaign for Vans is exposed by Blackbird Spyplane.
    • “...you could find inaccuracies ranging from weird fabric glitches to a model’s foot bending 90 degrees the wrong way.” – Lauren [66:25]
  • Chelsea: “It is really crazy because it’s so obvious and AI does make mistakes, but under normal circumstances, someone comes in and retouches those mistakes so we don’t notice.” [66:25]
  • Consensus: AI’s growing role is concerning, and not even “AI Sam” can replace real photo shoots.

Notable Quotes & Memorable Moments

• On the Gaylor Fandom’s Reaction:
  “What if she’s really not queer at all?... I honestly think I could end up in the hospital or worse.” – Read by Lauren [19:41]
• On Elizabeth Gilbert’s Memoir:
  Chelsea: “She’s such a fucking junkie. I’ll just kind of like… have her get her pills mixed up.” [29:27] Lauren: “It is becoming abundantly clear that Elizabeth Gilbert is the definition of a woman that would do something for the plot.” [30:10]
• On Matching Celesbian Wedding Gowns:
  “Two white wedding gowns, that’s a lot. It’s a weird vibe. It’s like, look at Rebel Wilson’s wedding, you know... there’s something really campy about two wedding dresses.” – Chelsea [23:53]
• On Miley as Margiela’s Ambassador:
  Chelsea: “It made me want to cry, actually, when I first saw this. Or, like, throw my phone into the ocean a la Carrie Bradshaw.” [39:53]
• On SSENSE’s Buy Model:
  “They have everything. And yes, I don’t get the vibe that anyone ever pays full price for anything. I certainly never have.” – Chelsea [60:53]
• On J. Crew’s AI Photography:
  Lauren: “...you could find inaccuracies ranging from weird fabric glitches to a model’s foot bending 90 degrees the wrong way...” [66:25]

Timestamps for Key Segments

| Time | Segment | |-----------|------------------------------------------------------------| | 00:54 | Opening catch-up: canceled flights, wardrobe malfunctions | | 04:43 | Jury duty adventures & Cardi B trial recap | | 09:21 | Powerball fever & Burning Man chaos | | 14:59 | Taylor Swift’s engagement (the fandom, clues, wedding talk) | | 19:41 | The Gaylor subreddit meltdown | | 23:20 | Celesbian news: Chloe Grace Moretz’s wedding, lawsuits | | 29:27 | Elizabeth Gilbert’s wild memoir | | 35:15 | Sapphic YSL campaign, celesbian campaign analysis | | 39:53 | Miley Cyrus for Margiela (and the brand’s contradictions) | | 44:52 | Venice Film Festival fashion | | 52:08 | Giorgio Armani’s passing | | 55:13 | Vogue shakeup: Chloe Malle’s new role | | 59:33 | SSENSE bankruptcy: sales model, industry effects | | 66:25 | J.Crew Vans AI campaign—the rise of “AI slop” |

Tone and Takeaways

Chelsea and Lauren’s breezy, sardonic banter is rich with fashion trivia, incisive commentary, and internet-savvy cultural analysis. They cover headline news, but never without a wink—or a shade of skepticism for the ever-corporatized and AI-infused fashion world. This episode will satisfy anyone who loves fashion drama, queer pop culture, and unapologetically bitchy, insider commentary.

Further Listening

If you enjoyed the deep dive into celesbian weddings, queer internet drama, or the fashion industry’s existential woes, check out their hotline episode next week or revisit earlier episodes for more takes on Sex and the City and fashion’s wildest stories.