The Best Vintage Christmas Looks Of Classic Fashion Icons

By Nicole Andre
·  6 min read
vintage fashion icons christmas

It’s that time of year again! The holidays give us so many occasions to dress up, and nobody did holiday style better than the classic fashion icons of the past.

Over the years the world has grown much more casual, and while that has its perks (hello, getting all dressed up can feel exhausting, especially if you do it on a regular basis), at the same time with the formalities of the past went a lot of the glitz and glamour that made old photos look so magical. 

The thing is, getting ready is one of the fun parts of life, and during the holiday season particularly, we have the chance to make it special. So in the spirit of Coco Chanel’s saying that “a girl should be two things: classy and fabulous,” let’s take a trip down memory lane of Christmases past for our holiday outfit inspiration this year.

Grace Kelly Wraps Presents in a Sweet Headband

grace kelly wrapping presents black dress black headband

What better image to start with than this one of Grace Kelly wrapping presents in the chicest holiday ensemble? I promise that a little black dress and a black velvet headband are the perfect combination for just about any event you have this holiday season. Even if it’s just to feel extra ladylike while wrapping your gifts. Maybe it will inspire you to put a little extra effort into creating a gorgeous parcel — she sure did! I like to think that this option from Jennifer Behr is one the Princess of Monaco herself would be seen in.

Audrey Hepburn Knew a Thing or Two about a Fabulous Winter Hat

audrey hepburn fuzzy white hat winter

I can’t begin to tell you how obsessed I am with the darling hats that Audrey Hepburn wore at Christmastime. Maybe this year, ditch the beanie in favor of a gorgeous white fur (or faux-fur) hat or fuzzy earmuffs. It takes the same amount of effort as putting on a beanie and yet is a thousand times more feminine. 

Audrey-Hepburn-With-Santa-Claus white earmuffs

You’re bound to feel like Audrey in this glamorous fur hat from Overland or in this one that’s faux fur. But if that look feels like a bit much, fuzzy white earmuffs are a chic (and more subtle) place to start.

Who Says Dressing Like Mrs. Claus Has To Be Frumpy?

elizabeth taylor red White fur dress

Elizabeth Taylor is smoldering in this Mrs. Claus-inspired look. Winter is the best excuse you can get to wear fur. Pair it with a rich red dress and you've got a showstopping look!

Rita Hayworth Is Ski-Chic

rita hayworth skiing

Don’t think ski-chic is a thing? You probably never saw Rita Hayworth. It’s obviously a more casual holiday look as she’s doing an athletic activity, but yet she keeps so much of the glamour that was a part of her era with a jacket that has a feminine cut and her bold lipstick. Want ladylike style this holiday season? Choose feminine cuts that emphasize your waist and never forget your lipstick. Oh, and like Audrey, Rita never underestimated the power of cute winter accessories for looking youthful and ladylike all at once.

Grace Kelly Nails the Red Gown Look

grace kelly red christmas dress fur cuffs

Grace Kelly clearly knew the power of a glamorous red gown. You can keep that in mind for any holiday parties you might have. And since a gown might be too over the top, a red velvet dress is a perfect alternative. 

But even if you skip out on the red dress, you can embrace Old Hollywood style with your hairdo. Today we tend to wear loose curls anytime we get dressed up. Whatever happened to the fabulous and yet simple up-dos as seen on the likes of Grace Kelly? A sleek bun is easy to do. Get your regular hairbrush, a smoothing brush (it has softer bristles than the one you use to get your tangles out), hair ties, and your bobby pins (these ones from Sally’s are better than the drugstore ones, are cheap, and come in different shades), and get to work. 

Pearls Are Appropriate for Christmas Morning, Just Ask Jackie

jackie kennedy christmas morning pearls pink outfit

You might currently take more to going downstairs with the family in your matching pajamas on Christmas morning. I love them too, trust me, but I would be lying if I said the idea of wearing pearls and a pantsuit like Jackie did doesn’t seem magical. This might be way more formal than current standards of dress for Christmas morning (or any morning, really), but it’s your house, so if it sounds like fun and you want to watch old movies and pretend to be from another time and place, go for it, girl!

Sophia Loren Shares A Festive Toast

sophia loren christmas champagne toast

Even though her dress is simple, Sophia is the picture of class as she cheers over her miniature Christmas tree. Why shouldn't you decorate (and celebrate) in an elegant housedress? Take a leaf out of Sophia's book.

What’s Chicer Than a Green Wrap and Tulle?

audrey hepburn white dress green wrap

I’m in love with this photo of Audrey going down the staircase while filming Funny Face, as are many people. After all, Emily in Paris even gave a nod to the moment on the show. And while Audrey may not have been wearing this at Christmas time, the green and the tulle strike me as being perfect for the holiday season. Somebody, please wear this when you go see The Nutcracker. After all, Audrey loved ballet.

A Sweet Red Velvet Dress

rita hayworth christmas

What better for celebrating the most wonderful time of the year than an absolutely darling red velvet dress, trimmed in fur? The subtle detail of the dark nylons ages the look up a bit, and turns it into a flirty, romantic look.

Gold for the Holidays

elizabeth Taylor gold dress christmas style

Doesn’t Elizabeth Taylor just sparkle in this gold dress? It’s gorgeous and a shade that’s pretty much only appropriate during the holiday season, so make the best of it while it’s here because after New Years’ it becomes a lot harder to wear.

There’s No Bad Weather, Only Poor Choices in Clothing

audrey hepburn black coat playing in snow

Look at Audrey Hepburn embracing the Scandinavian approach to weather! A good coat and some gloves, maybe a scarf, and you’re suited up for all the winter outdoor fun. 

audrey hepburn scarf throwing snowball

And after all, happy girls are the prettiest, so getting outside to avoid the winter blues is the ticket to Audrey’s approach to beauty. I mean, just look at that smile.

Embrace Your Traditions

ingrid bergman st lucy day traditional swedish costume

Ingrid Bergman played many different characters, but she wasn’t afraid to let the holidays take her back to her Swedish roots. Embrace your traditions this holiday season! Wear the heirloom jewelry, wear the traditional Christmas dress of your heritage, put the Christmas dress you wore as a girl on your daughter. Or hey, keep your tradition of matching pajamas! The holidays are the perfect time to remember where you come from.

Closing Thoughts

Want to embrace the glamour and glitz of Hollywood starlets and classic fashion icons during the holiday season? It’s way easier than you think. And the little bit of extra effort it takes to get ready will be well worth it. So go ahead, dress up, and maybe put on old Christmas movies while you wrap gifts.