Red Carpet Flashback! These Photos fromThe HolidayPress Tour in 2006 Will Make You Nostalgic

Mar. 15, 2025

Cameron Diaz, Jude Law and Kate Winslet attend “The Holiday” premiere in London in 2006.Photo:C. Uncle/FilmMagic

C. Uncle/FilmMagic

This holiday season, we’re looking back at the sartorial selections fromThe Holidaypress tour, which saw the film’s starsJude Law,Cameron DiazandKate Winslettake on the carpet in glam ensembles fit for a Hollywood eventanda festive Christmas party (naturally).

There’s a lot to dissect with the cast’s ensembles along the press tour from 2006 (it was a different time, after all), but the overarching theme appeared to be business-casual glam.

On the day of the film’s Nov. 29, 2006, release, the trio (who star in the Nancy Meyers classic alongside Jack Black and Eli Wallach) coordinated in gold and black.

Cameron Diaz, Jude Law and Kate Winslet attend “The Holiday” premiere in N.Y.C. on Nov. 29, 2006.Lawrence Lucier/FilmMagic

Lawrence Lucier/FilmMagic

Diaz, who famously played Hollywood exec Amanda Woods, wore a floral gold minidress accented with flutter sleeves and a two-toned metallic ruffled hem, which were signature to the 2000s. Her hair also went from her silver-screen blonde to a darker brunette color, but her on-trend side bangs stayed the same.

She wasn’t the only one to switch up her look post-filming. Winslet, who played journalist Iris, took her ginger blonde hair to a light golden shade, which popped against her satiny all-black skirt suit.

Law, in charge of the ever charismatic Graham, suited up in a black two-piece, a striped tie and a white button-up shirt with a contrasting black collar (a total throwback).

Cameron Diaz, Jude Law and Kate Winslet match in black outfits for “The Holiday” premiere in London.Fred Duval/FilmMagic

Fred Duval/FilmMagic

On Dec. 5, the stars flew out to London for theHolidaypremiere there, and this time they matched in black ensembles with Diaz in a floor-length halter dress with a metallic sheen and Winslet in a mini velvet confection with bows and tulle. Law wore a gray blazer and sheer vest over his collared shirt.

Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.

SinceThe Holidayhit theaters 18 years ago, there’s been a few behind-the-scenes secrets that’ve been spilled from the cast and crew, making it a forever conversation piece.

“That cottage doesn’t exist,” Law confessed. According to the actor, director Meyers couldn’t find the perfect house, so she decided to rent a field and build the cozy home from scratch.

Cameron Diaz, Jude Law and Kate Winslet.E. Charbonneau / Staff / Getty

E. Charbonneau / Staff / Getty

The PEOPLE Puzzler crossword is here! How quickly can you solve it? Play now!

“So here’s the funny thing, if you watch it . . .We were shooting in the winter here. And every time I’d go in that door, we’d cut, and we shot the interiors in L.A. about three months later,” he added.

Way before it even came time for our annualHolidayrewatch, Law toldE! Newsin June thathe “love(s) the idea"of a potential sequel to the classic. He teased the prospect alongside Meyers in an Instagram video of himreenacting his famous Mr. Napkin Head scene.

Earlier this month, costume designer Marlene Stewart, who dressed the ensemble, shared with PEOPLE exclusivelyfew fun tidbits about the iconic looksfeatured in the movie, from Amanda’s quiet luxury ensemble (which was ahead of its time) to Iris’ athleisure ensemble.

source: people.com