For their first red-carpet appearance as a couple back in May, Timothée Chalamet and Kylie Jenner wore matching all-black looks to the David di Donatello Awards, which are Italy’s version of the Academy Awards.
Since then, speculation has been rampant that their relationship could be in trouble. Those flames were fanned when Mr. Chalamet declined to comment about Ms. Jenner in an interview with Vogue last month, adding, “I just don’t have anything to say.”
This week, at the Los Angeles premiere of “Marty Supreme,” Mr. Chalamet’s film about a table tennis player, the couple appeared in shockingly bright orange ensembles that tied in with the marketing of the movie and were coordinated to the point that they felt like an attempt to loudly project that their relationship was safe.
“Matching on the red carpet is one of the oldest plays in the playbook,” said Lauren Beeching, a crisis public relations agent based in London.
While “Marty Supreme,” the A24 film that Mr. Chalamet produces and stars in, has leaned on a ’90s-style windbreaker as its main piece of merchandise, the couple’s appearance also recalled the end of that decade, and the early aughts, which was a golden era of sorts for celebrity couples. It was the decade of couples like Britney Spears and Justin Timberlake or Victoria and David Beckham, showing up on red carpets in matching monochromatic hues that were so memorable they still get brought up two decades later.
If the Chalamet-Jenner coordination seemed a little less fun, that may have been by design.
“It’s the ’90s form but updated for an era where every appearance is dissected, shared and debated on social media,” Ms. Beeching said. “The modern version is less about romance and more about managing expectations.”
In 2001, Ms. Spears and Mr. Timberlake appeared on the red carpet for the American Music Awards in matching patchwork denim that stretched from Mr. Timberlake’s hat to Ms. Spears’s floor-length skirt. In 2020, Steven Gerstein, Mr. Timberlake’s stylist from that era, spoke with Jezebel about how organically the look came together.
“It was just two kids, wanting to do something cool, and being super cute, matching,” Mr. Gerstein said. “It was kind of like their prom.”
The Zoe Report, an online fashion publication, included Ms. Spears and Mr. Timberlake in a 2021 piece, “The 2000s It Couple That Shaped My Early Views on Love & Relationships,” citing their matching denim outfits as a reflection of “this magical couple.”
They were hardly the first. In 1999, Victoria and David Beckham attended a Versace event in matching leather Gucci outfits, finishing the look off with dramatically gelled hair.
“We really considered those outfits,” Ms. Beckham said in an appearance on “Watch What Happens Live” in 2022. “We really thought about it. There was a naïveté to it that was just so sweet.”
That quaint and youthful energy does not seem to be a predictor of relationship health.
While Mr. and Ms. Beckham have been together for over 25 years — they got married later that year in matching dark purple outfits — Ms. Spears and Mr. Timberlake had a tumultuous breakup that still finds its way into the discussion of both stars.
Another ’90s “it” couple, Meg Ryan and Dennis Quaid, were also known for wearing matching black outfits on red carpets, the most notable of which was when they wore matching black suits, white T-shirts and sunglasses at the 1996 premiere of “Dragonheart.” Their marriage ended after a decade.
Gwyneth Paltrow and Brad Pitt’s matching blonde pixie haircuts in 1997 couldn’t keep the couple together: Their engagement was called off later that year. And while ASAP Rocky and Rihanna have occasionally coordinated, to great effect and with great stability, Jason Momoa’s matching outfit with Lisa Bonet at the Academy Awards in 2019 could not keep that couple together.
Perhaps a better indicator for the Chalamet-Jenner relationship is the fact that members of Ms. Jenner’s family have been seen wearing the coveted “Marty Supreme” windbreaker in what feels like a show of support for Mr. Chalamet and his passion project.
And if things don’t work out, the orange outfits in Los Angeles, which screamed something between traffic cone and iPhone 17, can join the slide shows of the future alongside the Timberlake-Spears denim and the Pitt-Paltrow matching pixie cuts. Moments like those can last forever.
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