The 5 Most Stylish Holiday Movies of All Time
Five stylish films to watch while holiday hibernating.
With the holiday season comes a considerable amount of down-time. Seasonal work schedules, designated time off, and (typically, hopefully) a fair amount of snow on the ground all point to one activity; hunkering down indoors with a few festive films on deck.
Of course, there are the classics – Home Alone, A Christmas Carol, and more recently, Will Ferrell’s Elf, however, for the sartorially-minded viewers, we can’t help but notice that certain holiday films are better than others when it comes to style cues. If you consider yourself in that camp, here’s what you should be watching this season.
James Stewart, Ernie Adams, Ellen Corby, and Jimmy the Crow in It's a Wonderful Life (1946)One of the most referenced, quintessential holiday movies in history, It’s a Wonderful Life follows the life story of George Bailey (James Stewart), a kind-hearted man who – very much in the spirit of the holidays – continues to sacrifice his own dreams and aspirations in order to help the citizens of his hometown, Bedford Falls.
As the film spans over the course of George’s life, notable fashion trends from the 1910s to the mid-40s feature throughout, showcasing a variety of casual and workwear-inspired looks along with suits and tailoring, of which micro trends are notable across the decades. The clothing history embedded into the film’s costume design is one to marvel at, with standout pieces from specific timeframes celebrated on-screen in each chapter.
Jack Lemmon and Hal Smith in The Apartment (1960)When Manhattan insurance clerk Bud Baxter (Jack Lemmon) attempts to get ahead in his company by allowing his bosses to use his downtown apartment for their extramarital affairs, office politics inevitably get in the way, and he’s left with more than he bargained for. This classic holiday-themed Rom-Com playfully takes a satirical perspective on corporate culture, inter-personal relationships, and the pitfalls of personal greed.
If you’re a fan of timeless style (not to mention incredible cinematography), this is the holiday film for you. Mid-century Manhattanites have been endlessly depicted in movies and TV, though arguably never as alluring as in The Apartment. Sharp suits, skinny ties, trench coats, and perhaps the last (and best) era of men sporting fedoras and bowler hats epitomize the style on show in this must-see movie.
Bill Nighy, Sarah Holland, Meredith Ostrom, Clare Bennett, Sarah Atkinson, Vicki Murdoch, Katherine Poulton, and Tuuli Shipster in Love Actually (2003)A beloved holiday cult classic, Love Actually is a charming Rom-Com that follows storylines of multiple different characters that inevitably intertwine throughout the film. Taking place during the weeks leading up to Christmas (and then afterward), the festive spirit and utter hilariousness of the film grows greater from scene to scene.
An exhibition of early 2000s style, the clothing featured in this London-based movie is a capsule back in time to when chunky knitwear, structured shoulders, vibrant button-ups, and low-rise jeans were all the rage. From the characters’ costumes to their Y2K hairstyles to their many memorable moments on-screen, Love Actually is a film chock-full of personality.
Cate Blanchett and Rooney Mara in Carol (2015)Set in the 1950s, Carol follows the story of Therese Belivet (Rooney Mara) and the title’s namesake Carol Aird (Cate Blanchett), whose introduction in a New York City department store slowly evolves into a love affair. The story explores the societal risks of their homosexual relationship and the struggles that came with it at the time, all the while (more positively) accurately depicting the irresistible fashion of the era.
A masterclass in mid-century style, every still from Carol could be a fashion poster in its own right. Luscious mink coats, pristine suits and tailoring, covetable cuts and proportions, and so much more allow the film’s impeccable costume to take a starring role. Even the most anti-fashion viewers will come away with some sartorial inspiration.
Brady Hepner, Ian Dolley, Dominic Sessa, Michael Provost, and Jim Kaplan in The Holdovers (2023)Despite being the most recent release on this list, many proclaimed The Holdovers as an instant-classic when it hit theatres ahead of the holiday season in 2023. The film takes place in a New England-based prep school during the holiday season of 1970. When Scrooge-esque history professor Paul Hunham (Paul Giamatti) is unwillingly tasked with supervising a group of students unable to return home over the winter break, his hardened demeanour slowly melts away while his compassion and understanding for the misfit “holdover” students grows.
Many revere the 1970s as their favourite style decade and it’s easy to see why based on this film. A deepened sense of nostalgia runs throughout, including into the characters’ costumes, with styles like duffel coats, sweater vests, elongated collars, and a healthy dose of corduroy repeatedly featured. Between his bushy moustache and lazy eye, Paul Giamatti’s character poses an unlikely source of style inspiration, though one can’t help but fall in love with his dismissive disposition and insouciant concern about image, amounting to a certain star-worthy personal style.