It’s hard to believe that the 2025 holiday season is here: Where did the year go?
We, personally, are ready for a break—whether that looks like cozying up to some hot chocolate with your closest family or going on a little festive getaway with friends. Whatever your social calendar looks like these next few weeks, one thing is for sure: You are going to need many festive outfits. And what better place to look, than to some classic Hollywood cinema?
There are a number of style lessons that I have learned while recently giving these beloved films a rewatch. If your personal style leans more minimal, for instance, perhaps Cameron Diaz (and her head-to-toe cream wardrobe) in The Holiday can ignite some fresh ideas. More of a maximalist? The fabulous Martha May Whoovier in The Grinch could be your girl for all things over-the-top (hair bows, anyone?).
Follow these festive rules, and you may just be the best dressed person at your next holiday party. Below, read on and explore 8 festive style lessons I learned from classic holiday films.
Embrace the skirt suit
Is there a more classic holiday film than Miracle on 34th Street? Old Hollywood star Natalie Wood commands virtually every scene she is, thanks to her elegant (and festive) outfits throughout the film—but her staple look is a tailored skirt suit. With her sharp shoulder-pad jackets and clean A-line skirts, she shows exactly how refined holiday dressing should be done. Sometimes, a more pared-back outfit can shine better than any shimmering crystal or bright hue. Plus, a striking two-piece is all of the rage in fashion right now.
Don’t forgo a statement coat
Do yourself a favor this holiday season, and do swathe yourself in cozy cashmere, just like Cameron Diaz does in The Holiday. Her delicious, all-cream wardrobe is simply to die for, but there is nothing more striking than her array of shearling statement coats. Both warm and stylish, they are the perfect outerwear for galavanting in the snow—while also possibly meeting a new love interest. If there is Jude Law lookalike who would like to stumble into our lives, we are open to it, too.
Lean into glitz
From pre-Christmas festivities to glamorous New Year’s Eve bashes, there is plenty to get dressed up for this month. So, imitate Queen Latifah in Last Holiday and do not be afraid to embrace both shimmer and metallics. Her golden jacket, complete with ruffled sleeves, that she wears while gambling at her ritzy hotel in Karlovy Vary? It would be the talk of any party.
Feathers and lace? Yes, please
While plushy velvets, lush knits, and shimmering sequins may be the most-known pillars of holiday ensemble, the stylish leading ladies of White Christmas show that lace and feathers can feel just as festive. And forget the obvious hues of red, green, or white: They prove that you can embrace an icy blue instead, and still feel totally on theme for winter. Also of note? Their monochromatic leather gloves. Bonus points if you can perform a full-on musical number in them.
Do add a jaunty little hat
“Kevin!!” We all grew up loving Kevin McAllister (Macaulay Culkin) in the Home Alone franchise. His cozy little outfit in Home Alone 2 especially resonates: He jaunts around New York City, totally on his own, while keep his head warm with a perfect little striped pom pom hat. (Or a toque, if you prefer the Canadian term.) Doing any sort of holiday activities this month—skiing, caroling, tree shopping—means you must keep the ears toasty at all times. You might as well look adorable while doing so.
Don’t be afraid of winter whites
Wearing all-white is always a challenging proposition for any holiday party—especially if you are near red wine or virtually anything that can spill—but if Whitney Houston proves anything in The Preacher’s Wife, it’s that head-to-toe cream is enduringly polished and well worth the risk. Her embellished skirt suit, paired with black knee boots, feels timelessly elegant, and right on theme. It is also a less on-the-nose approach than, say, a red dress with white trim. Think of it as less Mrs. Claus, more chic.
The chunkier the knit, the better
Let’s face it: When you’re lounging around at home during the holidays, you aren’t dressing up in a full-on runway outfit. A chunky sweater suddenly becomes the most important piece in your closet. So, do like the kooky family in The National Lampoon’s Christmas Vacation, and embrace an extra-thick version—in festive colors, a 1980s-style Fair Isle pattern, or cable knit. You can always dress the sweater up by layering a collard shirt underneath. Or, you can sport it with your best sweatpants and a cup of hot cocoa, of course.
Add a little hair bow—or several
We will declare it now: Martha May Whovier (Christine Baranski) in The Grinch is a style icon. A holiday maximalist, she simply loves glamour and excess—right down to her affinity for hair bows and bling. Consider it a prime lesson: Do not ever forget to accessorize! She makes the case for jewels belonging on your neck, ears, and even in your tousled updo. Think that’s a little too much? Wear a singular statement hair bow with your finest flannel PJs and call it day. Low effort, high impact.
