Spoiler alert: The Holiday is a crowd favorite.
Few adults have a schedule that accommodates a mid-afternoon double feature. But as soon as vacation rolls around, or even a plans-free weekend, many of us can be found catching up and reconnecting with films whose plots we know by heart—and yet, they never get old. Especially this time of year. With the holidays around the corner, naturally, some of our favorite tastemakers have lined up an afternoon binge-fest.
Instead of curating closets or an outfit, the fashion insiders below are helping cue up a full day (or a few) of entertainment with their favorite movies they watch whenever they have some extra downtime. While some can agree on seasonal classics—The Holiday and Elf are unbeatable crowd-pleasers—these designers, buyers, and influencers also share more unexpected pieces of cinematic history worth making time for. In between stuffing stockings and 3 p.m. naps, that is.
Read on for an entire holiday vacation’s worth of movies that have earned the stamp of approval from a discerning fashion crowd.
“The clothing, storyline, and cast are all top-notch! It's also a family tradition to watch whenever we're all together and that's typically during the holiday season.”
“I've loved this movie since I was a teenager. There aren't a lot of Black love stories out there in the movie universe and watching this over and over never disappoints. It's also hilarious!”
“Who wouldn't want to house-swap with a stranger and fall in love in the process? This movie is a tad unrealistic in today's age, but the home decor is unmatched.”
Kellie Brown, influencer
“I really enjoyed last year’s Jingle Jangle, so I’ll be rewatching that for sure!”
“Classic Home Alone is always on my list.”
“I just missed the Annie Live! remake but hoping I can catch it online!”
Brittany Xavier, influencer
“We love watching the Hallmark Christmas movie channel for Countdown to Christmas as a family. The movies are lighthearted and appropriate for us to watch with [my daughter,] Jadyn."
“Jadyn and I started watching Maid on Netflix together, and it’s very good. We're looking forward to finishing the season together over the holiday break."
“ The Family Man and Four Christmases are two of my favorite holiday movies, so we’ll be watching those again, too.”
“Love Actually is my favorite holiday movie and it’s one I watch every single year. A lot of holiday movies focus on romance, but I love the various love stories from friends to family members and how all the stories are intertwined. I always cry at the end!”
“Elf is such a sweet movie around the holidays, and it reminds me to continue to bring joy and light into my life through fun and not take things too seriously!”
Any Holiday Baking Shows
“I’m a terrible baker, but I love to watch any of the holiday bake shows and binge tons of episodes—they get me into the holiday spirit without having to make my own baking mistakes. It’s so fun to see how creative they get.”
Alison Chemla, designer of Alison Lou
Photo: Courtesy of Alison Chemla
“One of my favorite feel-good movies (and maybe all-time movies). Every time I watch it, it just gets funnier. It’s the perfect flick to watch with family and friends this year if you’re in the mood for excess laughter!”
“I mean the title…duh! All-star movie, all-star cast, feel all the emotions while sitting on your couch and enjoying one of the best holiday movies.”
“I know it’s an obvious one but why not stay on theme and get in the spirit! It’s a classic holiday movie and I love that it takes place in my hometown of New York City.”
“The Holiday is always my number one go-to! I watch it year-round. It’s what I call the perfect movie. It has beautiful characters, an adorable plot line, all the Christmas feels, and makes me want to buy a cottage in England.”
“This has become a classic in my opinion. It’s just a silly time and fun to watch if you have kids.”
“This is a true classic. We have watched it every Christmas since I was younger, so it has become a tradition—and it still holds up! ‘It’s a beaut, Clark!’”
Sai De Silva, influencer at @scoutthecity
“When I have downtime during the holiday break, I tend to binge-watch all of my old favorite movies that aren’t necessarily holiday related. I get such a kick out of certain films, even if I can recite them up and down and backward.
“I was obsessed with this movie growing up. I love Vivian’s sass and spirit as she navigates the world of upper-class functions and proper etiquette. It's so fun to watch her transformation and of course, see all of her looks. I even dressed up as Vivian once for Halloween, but I'm not going to tell you which version of her I was.”
“There’s something about an underdog story that appeals to me and when you mix in luxury fashion, I can’t look away. The Devil Wears Prada will forever be one of the most quotable films and it reminds me of my comical days as a fashion intern. Sometimes the industry is a bit ridiculous, and it’s almost therapeutic to watch Andy be baffled by it, irritated by it, and then suddenly respectful of it. I think anyone who’s worked in the industry can relate to some aspect of this movie.”
“The outfits. The valley girl drama. The ’90s vibes. I'm here for it all. I love a glass of wine and a good chick flick when I have downtime, and this one never gets old. I totally idolized Dionne when this film first came out. She’s such an it-girl!”
Kristina Zias, model, blogger, and co-founder of The Confident Collective
“The Home Alone series is on repeat in my house from November through December. Do not sleep on Home Alone 3! It’s so funny and Scarlett Johansson is in it, need I say more?”
“I’m obsessed with Miracle on 34th Street. It is such an iconic movie and so sweet and wholesome, and the fashion and style is so chic and timeless.”
“My favorite holiday rom-com is The Holiday. I watch it every year multiple times and love seeing the juxtaposition between the English countryside and Los Angeles. Also, the love stories are everything I could ever want and more!”
“The three movies I plan to watch this holiday season are all extremely cozy, comfort food nostalgic soothing films. There is nothing in this world I love more than getting cozy on my couch with my heated blanket and copious amounts of snacks to watch a film. Nothing!
“I'll start with Amelie, which absolutely shaped who I am. It is the most beautiful film in the entire world. It's an appreciation of the idiosyncratic characters and things that make our lives more interesting and textured. It transports me to Paris.”
“I'll follow this with Chocolat, another ocular confection. I love movies that transport me to another time and place. Chocolat sweeps me into a small French town disrupted by a beautiful woman (played by one of my favorite actresses, Juliette Binoche), a restless chocolatier. I've seen it nearly 25 times and it's delightful each time!”
“Finally, the last film I'll watch during this cozy time is a film that warms my soul and heart: Inglourious Basterds. I can recite this film word for word and I find it so deeply satisfying each time. Spoiler alert: One of the most evil people alive dies in this film. It's so gratifying.”
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