This Season, I’m Looking To These Holiday Icons For Style Inspo

‘Tis the season to take your style game to the next level. While many may be turning to TikTok for all their holiday outfit inspo, this fashion editor is looking to the past — both distant and not-so-distant. Yes, as an avid pop-culture fanatic, I’m finding the best inspiration — and the most varied — in the holiday season’s most iconic It girls. Longtime seasonal sensations, from Judy Garland to “Queen of Christmas” Mariah Carey, are lighting up my creativity with their glitz and glam from decades of yore.

The beauty of going down memory lane is that there’s so much to glean in terms of aesthetic. Garland’s sweet, turn-of-the-century style in the holiday classic Meet Me in St Louis, is ideal for coquette and cottagecore lovers alike. Those with a flair for retro-glam, and any sort of animal print, should look to “Santa Baby” singer Eartha Kitt, whose renown extends past her distinctive, purring voice. And, of course, one can’t discuss the Christmas holiday without bringing up the aforementioned Carey. While the singer’s seasonal streak is still going strong today, it’s spanned decades, dating back to her first holiday album, Merry Christmas, which included the winter mega-hit “All I Want For Christmas Is You.”

“Each year, this woman makes money in droves because people cannot get enough of her holiday spirit — she wrote all the original tracks on her holiday album herself and every November, ‘All I Want For Christmas is You’ shoots up the charts as people prepare for her to declare, ‘It’s tiiiiiime,’” says beauty editor and pop culture aficionado Kirbie Johnson. “Everything this woman does around the holidays has a touch of fairy dust.” Like her songs, Carey’s style power hasn’t wavered for 30 years, thanks to her love for glitzy, fitted gowns and sparkling accessories (perhaps it’s all that fairy dust, no?).

Ready for a visit from the divas of Christmas past (and present)? Scroll ahead for the five holiday queens guiding my style choices this season.

Judy Garland

Although Garland’s star was originally set with her role as Dorothy in The Wizard of Oz, her status as a holiday icon came with Meet Me in St. Louis, where she first introduced the world to the legendary song “Have Yourself a Merry Little Christmas.” Donning a rich red puff-sleeve gown with a sweetheart neck, a string of pearls, and silk gloves, Garland was the original pioneer of the uber-popular cottagecore aesthetic. This is the image that’s now splashed on nostalgic seasonal items like tree ornaments and holiday cards.

In general, Garland naturally embodied the Old Hollywood glamour that people associate with the warmth and elegance of the festive season. Her looks were refined yet approachable, with a mix of sparkle, tailored silhouettes, and soft curls that evoke vintage Christmas charm. Yes, please.

For holiday 2024, lean into the throwback vibes via a classic red dress with exaggerated sleeves, cinched waist, and flared skirt (midi or mini). To really drive the sweetness home, pair the look with lace ankle socks, Mary Janes, and a hair bow. Do Judy proud.

Eartha Kitt

Arguably the original sex symbol, Eartha Kitt’s “Santa Baby” is inescapable this time of year — you can’t enter a department store or market without hearing that familiar baritone opening. Love it or hate it, it’s truly iconic, hence it’s been re-created and reimagined dozens of times by singers like Madonna and Kylie Minogue, all attempting to capture the effortlessly sultry essence of the cheeky tune. The thing is, a crucial component of the magic of the song is in its original singer, whose natural sex appeal solidified her as a cultural and style icon.

“When I sat down to watch a Kitt performance from 1953, it became immediately obvious that it’s nothing like the ‘Santa Baby’ I had come to know and loathe,” recalled writer Caroline Framke in a 2013 article for the AV Club. The journalist went on to describe Kitt as “electric,” in the sense that “if you got too close, you’d feel the thrill of a static shock merrily buzzing through your fingertips.”

Indeed, in the original video recording, Kitt is wrapped in a white fur that serves as a sort of blanket-dress hybrid, revealing her shoulders and most of her back. She’s wistfully looking out a snowy windowscape, belting a wishlist of sables, yachts, and convertibles out of her ruby-red lips while insisting she’s been an “awful good girl.” Electric, indeed. This picture is essentially what rocketed Kitt to pop-culture icon status: her penchant for audacious, sexy, and luxurious looks and fearlessness in showing a bit of skin. Some of her style signatures included fur coats, leopard print everything, body-hugging cigarette pants, and the long strand of pearls she wore with even the simplest of looks to add a touch of glam.

If you, too, are looking to up the ante on your holiday smolder, perhaps take a page from Kitt, and go for bold.

Catherine O'Hara

Kevin! While not the most obvious one on this list, one can’t deny the holiday appeal of Catherine O’Hara in the first two Home Alone films. In addition to being the quintessential movie mom — despite, you know, leaving her 8-year-old at home alone — her wardrobe in the inaugural 1990 film was truly chic. Set in the midst of a Chicago winter, O’Hara’s ensembles as Kate McCallister were chock full of sleek ‘90s staples like chunky cable knit sweaters, neutral longline overcoats (accented with printed silk scarves), and tailored chinos and pleated trousers.

As a child, I didn’t put much thought into O’Hara’s style moments as she just personified the typical ‘90s mom. However, some 30 years later, I can’t get enough of her fashion formulas. In fact, her looks very much align with the sweeping menswear trend that’s hitting hard this fall. Yes, It girls like Hailey Bieber, Ciara, and Kristen Stewart are all current champions of the androgynous aesthetic. But, never forget who walked so they could run: Ms. O’Hara.

For holidays on the road or more laid-back seasonal affairs, Kate McCallister’s wardrobe is definitely one that will serve you well, as it’s as practical as it is chic. You likely already have a number of the essentials sitting in your closet. For the 21st-century holiday, try elevating the chino-infused outfit with some of-the-moment slouchy ankle boots and trousers in a trendy shade like chocolate or heather gray.

Dolly Parton

“Dolly Parton is holiday personified,” says Johnson. “Her wit, beauty, and generosity make everyone smile; her wigs are gifts in themselves. I think of her holiday party look in Steel Magnolias at least once a month.” Yes, Parton’s fur-lined white holiday party sweater in the 1989 classic has forever committed her to memory, but she’s also made seasonal style magic on her own accord. Ever the rhinestone cowgirl, one can always count on the singer for a thigh-skimming A-line mini dress, a luxe pair of Western boots, and — of course — sky-high hair. What else would one wear when belting out a Christmas classic?

And while this is all enough to cement Parton in holiday history, Johnson explains that her seasonal connection to Parton hinges on the singer’s ability to sing “one of the saddest Christmas songs of all time” — a song that wasn’t meant to be holiday-adjacent to begin with. “It’s from a Broadway musical-turned-movie about a brothel,” explains Johnson. “‘Hard Candy Christmas’ brings grown men to tears (if you believe the YouTube comments). It’s a tender song about finding the sweetness in the small things and persevering through difficult times, a sentiment that’s just as relevant now as it was in the early 1980s [...] Of course Parton would be the only one able to weave a number from a musical with ‘whorehouse’ in the name into the fabric of Christmases past and present.”

Mariah Carey

“She is Christmas,” says podcaster and pop culture expert Danny Pellegrino of the music legend whose holiday reign dates back to the ‘90s and only gets more prolific with each coming decade. (“All I Want For Christmas Is You” has sold 16 million copies worldwide to date, making it one of the bestselling digital singles of all time).

“Did you know she is a credited writer on ‘Where Are You Christmas?’ the Faith Hill song from 2000’s How the Grinch Stole Christmas?” Pellegrino adds. “That song is a soft-rock staple that consistently plays on holiday radio and very few people even know Mariah had a hand in it, which proves even her lesser-known Christmas output hits. I keep hoping for Mariah to find and release her original demo of the song.”

Carey has rightly capitalized — and monetized — on this niche success via multiple holiday albums and annual live performances, including 2024’s Christmas Time tour, which runs from Nov. 6 through Dec. 17. Last year, Carey even produced a viral social media video that shows her defrosting after Halloween, signaling the start of the holiday season. The singer steps out of a cracked ice encasement in the festive garb she’s now known for, darling. Yes, these days, you can always find the diva in her signature form-fitting glitzy gowns, voluminous waist-skimming curls, and sky-high stiletto heels. But, if you want to channel the singer’s ‘90s style, a festive red bomber thrown over a fuzzy cropped cardigan and straight-leg denim will also do the trick.