'Tis The Season

How To Recreate Taylor Swift's Best Holiday Looks Over The Years

For way less.

by Marilyn La Jeunesse
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To me, Taylor Swift is the epitome of holiday dressing. She’s proven time and time again that she can nail every single cold-weather outfit. From a cozy night indoors to an epic New Year’s Eve bash, her winter style is, in my opinion, where she truly shines.

Investing in a good pair of black knee-high boots is the first must-have for the ultimate wintertime Swift look. The second is to remember that there’s no such thing as too many sparkles — at least not ahead of the holidays, that is.

Below, you’ll find Swift’s best holiday looks and how you can recreate them for way less.

Cozy Holiday Bundling (2023)

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Last year, Swift braved the Boston cold to support her boyfriend, Travis Kelce. She paired her custom-made knit beanie with a gray Chiefs sweatshirt and a perfect plaid skirt. Not pictured are a pair of tights to keep her legs warm and, most likely, a pair of her trusted knee-high boots in black, of course.

Feeling Unmoored In December (2020)

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On Dec. 11, 2020, Swift released her ninth studio album, Evermore. Along with it, she gave us the ultimate casual December outfit: an oversized plaid maxi coat, a cozy black sweater, and *gasp* black skinny jeans. Regardless of your stance on the beloved millennial staple, you have to admit that the icon makes them look chic.

Do The Jingle Bell Rock (2019)

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If there’s one thing Swift is going to do, it’s serve lewk after lewk at the annual iHeartRadio Jingle Ball. In 2019, she rocked (get it?) this epic black sequined dress with hints of Christmas red and green delicately sewn into it. She paired the sparkly mini with a nameplate necklace, a pair of rhinestone fishnet tights, and over-the-knee boots to complete the ’fit.

Bored At The Holiday Party (2019)

The holiday party might be boring, but Swift’s outfit is far from it. She rocked this sparkly holiday look in 2019 in a photoshoot with British Vogue. Who would have thought you could match duller greens and reds with an unmissable silver sequined shirt? Not me, but I’m glad the stylist on this set did, because it served.

Pop Princess In Plaid (2014)

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Plaid is another one of Taylor’s favorite go-to holiday patterns. This holiday outfit from the iHeartRadio Jingle Ball is so perfectly 2014 that it hurts (in a good way, of course). Not only are the pants high-waisted with a tight taper at the bottom, but she’s rocking a micro crop top and black booties.

Champagne Problems (2014)

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While performing at Moet Chandon’s New Year’s Eve party in 2014, Swift proved there’s no such thing as champagne problems when you wear enough sequins. Once again, in true 2014 fashion, she rocked a micro crop top with a pair of high-waisted skinny pants and ankle booties. I fear she ate with this one.

Fringe (Taylor’s Version) (2009)

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Picture this: It’s December 2009, and you’re in the crowd at Jingle Ball. Swift just released Fearless and is a relatively unknown star. You’re the first to see her in a fringe sequin mini dress, which will become a staple throughout her career. Life is good.

Rockin’ Around The Christmas Tree (2007)

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In December 2007, shortly after the release of her self-titled debut album, Swift had the honor of singing at the 75th annual Rockefeller Center Christmas Tree Lighting show. She paired this epic floor-length ivory coat with a black mini dress, her signature fishnet tights, and black knee-high boots. While you can easily recreate this look for way less, I regret to inform you that her iconic sparkly guitar is much harder to find.