The Most (and Least) Stylish Holiday Movies of All Time: From Sequined Leotards to Pee-Stained Santa Suits
When thinking holiday outfit inspiration, your first thought probably isn't the Christmas movies of the 90s, otherwise known as the decade in which about half of its film productions came from a TV channel aimed at tweens (oh, Disney) and the majority of the other half now seem practically ancient. The reality, however, is that the 90s are still clinging to relevance fashion-wise — or, at least, the 90s as lived and worn by Courtney Love. But there was a whole other kind of 90s style, and one we can turn to for this year's holiday fashion inspo — the one filled with boxy women's suits and pleated pants. Or in other words, not the stuff that Pinterest board dreams are made of.
In case you missed my drift, I'm basically suggesting that Christmas movies can inspire your office party attire. Or party attire in general. And that doesn't mean I'm eggnog drunk (yet). There are truly some incredible fashion moments between all the tinsel and fur-trimmed horrors! Despite the fact that two of the least stylish decades are responsible for most of the movies we turn to for laughs and nostalgia during the holiday season (here's looking at you, 80s and 90s), classic movies kind of save the day here. Because there's more to Christmas movies of old than It's a Wonderful Life! And if nothing else, they're proof that the sparkly dress and red-lipped party look is nothing new.
Just recently (I'll admit), I watched a bunch of Christmas movies to see what outfit inspiration I could muster (granted, many of them were just full of blatant "NOPES"). These results can basically be summed up in one word: vests. But then I ranked the films themselves, from least to most stylish — because I'm pretty competitive like that. Some of my favorites did not stack up to the competition, no matter how badly I was rooting for them (sorry, Sleepless in Seattle). So let's go walking in a mom-sweater wonderland.
10. Bad Santa
Kenny Rogers once said, "You gotta know when to hold 'em, know when to fold 'em," and I really wish that everyone behind Bad Santa would have folded when it came to this movie. Aside from not really being funny, even a little bit, it's just a wasteland when it comes to fashion. It's set in a department store in the early 2000s, which should say everything you need to know about the depressing amount of polyester suits. Also, why is Lorelai Gilmore in leather pants? I hate everything about this.
The only reason to use this 90s, Tim Allen tale as your style inspo is if you want to look like Christmas threw up all over you. When a movie is set almost entirely in the North Pole, I guess that's what you get. There are Christmas sweaters, long underwear onesies on adults, and the ultimate fashion disaster known as Bernard the Elf. If you take one thing from this list, I hope it's to avoid anything that would make you look like Bernard the Elf.
Though we all thought Ellen was a major babe for a mom, the fashion in this movie is pretty much everything about the 80s that should be banished to the decade. You have your fussy blouses, loud printed sweaters and berets. Uncle Eddie brings the whole group down with his robe/toque situation and visible dickie to the point of absolutely no return. Laugh at this one, don't dress like it.
Do you want to know why Meg Ryan looks so sad in the picture up there? Because her outfits in Sleepless In Seattle sucked. I'm all for a realistic snapshot of how some women choose to actually lounge on the couch or the shapeless blobs we need to wear over our clothes to keep us warm in the December weather. But when one looks as cute as Ryan does in When Harry Met Sally, it's just hard to accept the sweatpants and tucked-in socks.
6. Die Hard
Is it a Christmas movie? Yes. Is it stylish? I say yes! The benefit of this not being your conventional holiday fare is that it's pretty much devoid of any of the offensive holiday garb. Bruce Willis with hair and in a dirty tank top is nice, but I'm into all the dudes in well-tailored suits and Theo's nerdy-chic, hunky mock turtleneck and glasses.
There are more elegant — but sexy — party dresses and adorable pajama sets than I even know what to do with in this movie, but the main selling point for me is simple: Morris Chestnut in a suit. I'll leave it there.
So, yes, it's all a little WASP-y in this one, but Diane Keaton's pajama and statement necklace game is so strong. Really, this fourth-place mention is for Diane Keaton. Claire Danes' pseudo-boho look really works for me and Dermot Mulroney is kind of boring, but also has the style I thought my husband would have, back when I was 12.
If I learned one thing about myself today, it's that I am clearly a big fan of a man in a tailored suit. With this film set on Wall Street, there are enough good suits in here to open up a Brooks Brothers. Mostly, I'm a fan of Jamie Lee Curtis' dress/fur coat look and those scalloped undies. Maybe not family dinner appropriate, but super hot regardless.
Now we're into classically stylish territory. The huge dresses and dainty collars speak to the femme in me on a very high level. Unabashedly feminine and frilly — and probably really impractical — the costuming in this musical is a complete dream. Throw in Judy Garland's perfect soft, short bangs and red lip and I'd watch this film even if it was on mute.
Did I go a little hard on red velvet, fur-trimmed monstrosities before? I don't think so, but I'm making an exception in this case — and I'd make an exception for Vera Ellen even if she wore socks and sandals. No matter what you're into fashion-wise, you'll probably drool over the outfits and be Googling retro hair tutorials before it's even over. Oh, you thought Beyoncé did embellished leotards first?
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