Holiday Inn (1942)
Bing Crosby and Fred Astaire star in this prequel of (loose) sorts to White Christmas. The plot revolves around an entertainer who escapes the biz by opening a Connecticut inn that’s only open on holidays. The only apparent draw of the inn is the elaborate performances that take place there. The plot sort of falls apart at the end, but there are two main reasons to re-watch this classic: Fred Astaire tap-dancing with firecrackers (seriously), and Marjorie Reynolds’ performance gowns. Good god, the glitter.
White Christmas (1954)
We all know the songs and even a few of Vera Ellen’s incredible dance routines from this Bing Crosby/Danny Kaye/Rosemary Clooney classic. But can we talk about the outfits? The stage costumes are among the most exquisite of the era, but even the Haynes sisters’ off-stage clothes look great! Behold just a few of my favorite looks. I could have screen-capped this entire film.
National Lampoon’s Christmas Vacation (1989)
The National Lampoon’s Vacation films serve as a time capsule of ready-to-wear looks throughout the 1980s. Personally, I’m partial to the ridiculous designer threads purchased by the Griswolds in European Vacation before the trip goes to total shit, but the look worn by Ellen (Beverly D’Angelo) in the main dinner scene is a masterclass on how to look sexy and family-friendly all at once. The peephole neckline/gaudy broach combo is classic.
Also, Eddie! With a belt holding his robe together!
Home Alone (1990) and Home Alone 2 (1992)
In the first Home Alone, Kevin McCallister’s sweater-and-pajama game is on lock. When he actually leaves the house in the sequel, Kevin’s on-point outerwear looks are surprisingly sophisticated yet age appropriate, especially considering he ended up in New York with only his father’s carry-on.
Also, we need to talk about cousin Fuller’s suspenders.
It’s a Wonderful Life (1946)
If one were to think of an iconic look from It’s a Wonderful Life, it would probably just be a disheveled George Bailey in his overcoat. Fashion and all its pretense could be considered a sort of antithesis to all that this film represents. But between George’s wife Mary (Donna Reed) and his dancer friend Violet (Gloria Grahame), there are some hints of glamour that peak through Bailey’s bleak worldview.
The Muppet Christmas Carol (1992)
Miss Piggy is a fashion icon in any era, but there’s something about the petticoats, ruffles, gloves, and big hats of the mid-19th century that suit her well in the role of Mrs. Cratchit.
Christmas in Connecticut (1945)
Barbara Stanwyck plays a single magazine columnist in New York, with what appears to be the perfect domestic life and a Connecticut farm. When her editor asks her to host a returning war hero at her home, she must orchestrate an elaborate charade in order to not appear a fraud. One thing that works to her advantage: her rich-lady ensemble of furs galore and elegant dresses.
A Christmas Story (1983)
Ralphie got his Red Ryder BB gun, but first he had to suffer through the most famous bunny costume ever committed to film. Thanks for nothing, Aunt Clara.
Miracle on 34th Street (1947)
In this classic, an eight-year-old skeptic played by Natalie Wood sits at the center of a court battle taken on by a sweet, bearded fellow with a serious Santa Claus complex. Come for the heartwarming absurdity, stay for Wood’s killer kid wardrobe of adorable outerwear and matching hats.
I remember approximately zero of Bill Murray’s outfits from his twist on A Christmas Carol, but can we talk about how psychotic and oddly attractive he looks in the movie’s promotional image? Has Bill Murray ever looked this good in a tux since? As for Scrooged‘s fashion game, Carol Kane’s Ghost of Christmas Present had Glinda-chic on lock.
Elf came out in 2003 and quickly became a timeless holiday classic. One aspect of the Jon Favreau movie that isn’t timeless: Zooey Deschanel’s street clothes. Out of her department store elf get-up, she’s looking positively early aughts. I’m a fan of the look above, though; to me, it updates some of the looks we see earlier in this very list, from the fur-trimmed coat to the funky hat to the red lip to the bouncing blonde locks. It’s not iconic, but she definitely looks better than Will Ferrell in a yellow leotard.
The Santa Clause (1994)
Tim Allen: the original lumbersexual?