Roundup! Iconic Holiday Looks Through The Years

We love a festive winter look! We're not religious, but we love this time of year. Christmas and New Year's Eve just bring a level of glamour and extra-ness that truly align with our values. To get you into the spirit too, we've collected some of the most iconic holiday looks of our lifetime. Here they are in all their glory. 

Mariah Carey, all I want for Christmas is you

Did you know Mariah makes $500,000 dollars every winter off of this song alone? That's because it is, indisputably, the best Christmas song of all time. And this video is just as legendary. It's shot like a home video, and Mariah is giving you girl next door realness, while still managing to be the top diva that she is. We don't know what we want more - the Miss Claus dress, the snow suit, or the red unitard with the white fur trim. Just, wow. 

Christine baranski in The Grinch


If Queen Frostine from the Candy Land board game were a character in a movie, she'd wear this look right here. But this isn't Queen Frostine, it's Martha May Whovier! And this looks screams "my uber rich husband died and left me everything and how DARE you show up to my estate unannounced. And on CHRISTMAS!" Her hair is perfectly blown out, her lipstick is an understated, the robe is expertly draped around her feet. Basically our life goal is to stay home forever and wear this every day. 

Sandra bullock in While You Were Sleeping

So ok...this one is actually us. The oversized sweater, the "mom jeans", that messy bun with the parted bang. It's effortlessly chill and cozy as hell with a smidgen of grumpy cat lady. And we heavily identify. This scene is us trying to be "hygge" during mercury retrograde.

N’Sync, Home For Christmas

Although we still don't fully understand the concept of a puffy vest in winter (it's just not PRACTICAL) we are still here for it's nostalgic value. The real showstoppers in this video, though, are the accessories. The headbands, the excessive use of goggles and that shiny green jacket/bucket hat combo...the late 90s were a truly wild time. Oh, and we gotta mention what's happening here with the hair. Not just frosted tips...but FROSTED DREADS. Was this actually a good look at the time? And another thing - was this video filmed with a green screen in someone's garage? We love it, honestly. 

Meg Ryan in When Harry Met Sally

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The New Year's Eve scene from this 1989 classic features our leading lady in a rooted golden blonde curly shag. And it's actually flattering and, in our opinion, very back. Paired with smoky eyeliner, peachy lipgloss, an off-the-shoulder dress and a faraway stare, you've got the perfect NYE look. Just add champagne. 

Winona Ryder, Edward Scissorhands

If you don't cry during this scene then you're dead inside. IT'S SCIENCE. Winona's strawberry-blonde fluffy hair and rosy makeup pair perfectly with her off the shoulder button down white dress. Off the shoulder was huge around the turn of the 90s! But the giant bow-like contraption attached to the left shoulder makes it really special. 

Sarah Jessica Parker, Sex & The City The Movie


SATC makes us laugh with what they consider "casual" clothes for their lead. In this scene, Carrie has been flopping at home all night and has just decided to run to Miranda's for the last minutes of New Year's Eve. So the idea is she's wearing her "chill" NYE look: expensive ass pajamas that may not even be pajamas, a fur coat, pearls, white gloves and booties, a sequined beanie and a sparkly purse. It's lazy and extra at the same time, and for that reason we love it. I mean seriously, SJP's hat here is ten times more fun to look at than the actual ball in Times Square. It's iconic as hell.

TLC, Sleigh Ride

TLC was always fashion goals, and they didn't disappoint in their Christmas classic. Their trademark oversized jackets, gold hoop earrings, and overalls of course make an appearance, but the all white outfits covered in red and green spray paint are a cute holiday touch. Makes us want to drive around in a decorated convertible and bring holiday cheer to the neighborhood. 

Catherine O’Hara in Home Alone 2

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Please look at this haircut! 1992 was such an amazing time for short women's do's, and this color with those big gold (probably clip on) earrings reminds us of our moms' casual day looks when we were kids. Should we bring back the curled bang? Maybe when shoulder pads come back! 

the Mean Girls "jingle bell rock" scene

Throwback to the time where girls wore camisoles as straight up shirts and flatirons ruled the world: 2004! This movie somehow feels contemporary despite coming out 13 years ago, but the outfits remind us of high school so, so much (remember flared jeans and those off-the-shoulder three quarter length shirts with the initials on the shoulder??) That said, if you ask us, a red pleather mini skirt is in style every Christmas, just like this iconic dance number. 

Jack Skellington, Nightmare Before Christmas

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Jack Skellington is goals! He made this entire winter look out of things he found in his apartment just so he could follow his dream of being the next Santa! When will your fav? Yes, this movie is animated, and yes, he's also a skeleton...but this fitted goth holiday look is inspiring us right now to get creative and follow our bliss even if it means potentially ruining Christmas! 

Lizzie McGuire, I Want Candy

Hilary Duff and since-cancelled pop star A*r*n C*rt*r took us on a little holiday ride in this early 2000s middle school cover of "I Want Candy" for Lizzie McGuire. When this aired in 2001 we were shopping exclusively at Old Navy and Limited Too which, if you recall, were stocking TONS of metallics and glittery items at the time. We were attempting to recreate Hilary and LaLaine's looks here, but it usually ended up with us wearing way too much frosted lip gloss to the winter school dance. 

Spice Girls

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Iconic all-white ensemble alert! This late 90s shoot is everything we want to be this winter, with the exception of the piece-y bangs on baby and those two blonde chunks framing Ginger's face (although Kat did do this to her hair in 2002. But that's neither here nor there!) Mod dresses, platforms boots, those jackets we all got from Delia's that had the fur trim...nothing screams "winter wonderland in the parking lot outside a dirty nightclub while on ecstasy at 4 am" quite like these ensembles. Ah, memories.

Destiny’s Child, 8 Days of Christmas

Two words: Beyonce's. Bangs. The girls look beautiful in this video even if they are inexplicably raiding a toy store after hours while also macking on guys. Michelle's outfit is surprisingly our favorite in this video. Those flared low-rise pants and fur-trimmed crop top are beyond flattering and make us miss those bare-torso days of the late late 90s. 

Miss Piggy, Muppet Family Christmas

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Last but not least, we have to include a puppet icon: Miss Piggy from the Muppet Family Christmas. Just pause and let the 80s wash over you. We're going to go get perms. 

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