Nancy Meyers’s The Holiday Still Offers the Best Winter Outfit Inspiration Nearly 20 Years Later
3 min readIt’s hard to believe the term “quiet luxury” had yet to enter the fashion lexicon when The Holiday hit theaters in 2006. Almost two decades later, the Nancy Meyers rom-com offers classic winter outfit inspiration that has stood the test of time—think plush cashmere and wool knits, expensive-looking outerwear, and an understated palette. The star-studded cast and cozy cabin aside—which, by the way, was replicated as a vacation rental in Georgia this year—costume designer Marlene Stewart’s timeless aesthetic is, in large part, what makes The Holiday a true cult classic.
Rumor has it that there’s an Apple TV+ reboot in the works, featuring the same home-swap premise with all-new characters (and hopefully, just as many moodboard-worthy looks). There’s no word on a release date yet, so for now, you can rent the original on Prime Video and shop your way through our favorite outfits from The Holiday below.
The impractical travel outfit that Cameron Diaz’s Amanda Woods wears is undoubtedly the film’s most iconic, so we have to start there. Let her loungewear inspire your airport looks (more on that later), and save this cozy shearling coat and cream turtleneck for an upcoming brunch or dinner reservation instead—and maybe consider swapping the stilettos for a more seasonally appropriate boot as well.
Now we can go back to the beginning. Amanda begins the film in sleek white pajamas, setting the tone for her understated color palette throughout. Add plush slippers, and you have the perfect outfit for a lazy day at home (and hopefully one that doesn’t involve a breakup).
In the Nancy Meyers cinematic universe, cozy cashmere and wool layers make the case that more is always more. Amanda’s layered sweaters and knit sweatpants would make winter bed-rotting feel like even more of a treat.
Over the years, Amanda’s wardrobe in The Holiday has been more widely celebrated, but Kate Winslet’s Iris deserves equal recognition. Swap the pajama pants for sweatpant jeans, and her taupe V-neck sweater and printed scarf feel just right for the season.
Throughout the film, Iris’s lightweight sweaters and jackets function as a foil to Amanda’s cold-weather attire. Should you be spending the season in a warmer climate, let fine-knit cardigans like this serve as inspiration.
We couldn’t help but notice Amanda’s brushed cashmere cardigan and layered white tees in this morning-after scene. Who but Amanda Woods looks this chic after a very long night out?
Amanda’s outfits in The Holiday make a strong case for a winter white handbag. This isn’t the same tote as the one featured in an earlier scene, meaning she brought not one, but two cream-colored carry-alls along on her trip to the Cotswolds. And can we talk about that coat?
Amanda admits to being “a tad overdressed” in this black-and-white pairing, which earns a cute “You look like my Barbie” comment from Graham’s daughter. Perhaps let it—and the chic wool coat she arrives in—inspire a dressier occasion, rather than a night in with the kids.
Iris and Amanda’s final few looks in the film prove that a classic LBD always fits the bill for holiday season festivities. If you’re still hunting for a New Year’s Eve look, consider this a sign to stick with tradition. Instead of a corsage, you can accessorize with a floral handbag or jewelry to the same effect.