The holiday season may be associated with bright festive sweaters and your comfiest, most forgiving pants, but cinema has a way of making every occasion seem stylish. We’re not talking about the large North Pole get-up from Elf or Kevin McCallister in Home Alone (he could barely shave!) but rather the small sartorial moments in Christmas scenes, like a festive-suited Robert De Niro in Goodfellas or Hans Gruber’s immaculate villain from Die Hard.
Regardless of what you’re lounging in over the holidays this year, here are seven films with enough style to keep you and your wardrobe happily entertained (and inspired).
Whit Stillman based Metropolitan loosely on his own life, following a group of socialites during the holidays, as they eat, drink and philosophize around Manhattan. It’s the cinematic version of an ’80s Paul Stuart holiday catalog come to life: tuxedos, satin bow-ties, foulard prints. It’s all worn with upper-crust panache by the young cast, convening around sparkling Christmas trees in Upper East Side apartments. There’s also that one scene where two characters debate the detachable collar: “So many things that were better in the past have been abandoned for so-called convenience.” A gem.
Kiss Kiss Bang Bang (2005)
Set in Los Angeles over the holidays, Shane Black’s slick noir thriller has more sunshine than snow but is still a darkly funny crime caper. A thief (Robert Downey Jr.), pretending to be an actor, is caught up in a murder investigation that involves a young actress—and a Raymond-Chandler-esque mystery unfolds. Each character seems as though they are dressed for a swanky Malibu party, especially Val Kilmer’s tough, gay hitman, Perry Van Shrike, who—however messy the job—still goes in looking like a movie producer. It might be the holidays, but this is Hollywood after all.
The Apartment (1960)
Manhattan in the holidays—is there any place more suited to the silver screen? The bright lights, brownstones and tungsten-lit office buildings in Billy Wilder’s 1960 classic form the backdrop for the story of Bud Baxter (Jack Lemmon), who naively offers his apartment for the extramarital affairs of his boss—until it all gets out of hand. Set around Christmastime, it’s plenty of fun seeing how smart office-wear once was. The annual party scene is reminiscent of the draped suits and slim ties from Mad Men. Moreover, Baxter’s tailored pajamas and his boss’s silk robe make great gifting inspiration for Christmas in 2020.
The Santa Clause (1994)
This 1994 film has become a bit of a cult favorite. It’s the story of an ambitious, neglectful divorcé who accidentally knocks Santa from his roof and must take his place. Not only is the film better than it sounds, but also includes arguably the most luxurious Santa Claus wardrobe on screen—from the plush, shimmering suit to Tim Allen’s silk pajamas (with S.C. monogrammed on the chest pocket). Even the North Pole appears more like a Fifth Avenue department store than a humble Arctic workshop. Keep an eye out for the surprisingly unoffensive Christmas sweaters.
A Christmas Tale (2008)
You just know the ‘bourgeois-bohemes’ at the center of this French family drama are going to dress with typical Gallic elegance. The troubled Vuillard family has plenty to unpack over the holidays, and thankfully that includes their wardrobes. Each character brings a style that not only reflects their personalities, but the type of impression they want to make on their terminally ill mother—from unloved son Henri’s slightly disheveled suit to family favorite Ivan’s colorful, patterned shirts. The thinking man’s Christmas movie.
The Holiday (2006)
In this more recent holiday favorite, Jude Law’s supremely charming single-dad looks the very image of the archetypical British romantic hero: structured wool overcoat, bookish tweed blazers, a light blue crew-neck sweater, thick plaid scarves, all topped by a stammering, sweetly awkward accent. You can easily imagine him rushing to the airport—scarf fluttering behind—to proclaim his love for Cameron Diaz’s jaded Hollywood producer. It’s a look many young British men have tried to cultivate since Hugh Grant in Notting Hill, and Jude Law pulls it off as well as any of them.
It’s a Wonderful Life (1946)
Is there a more definitive Christmas film than It’s a Wonderful Life? Perhaps Miracle on 34th Street, but that was never blessed by the slender grace of James Stuart. In Frank Capra’s tearjerker, Stuart plays George Bailey, a man who has given up on his dreams and decides to end it all on Christmas Eve. That is, until his guardian angel intervenes. Stuart’s wardrobe is classically American: schoolboy ties, soft-flannel tailoring, double-breasted overcoats and, in one flashback, a varsity sweater that wouldn’t be out of place in 2020.