Taylor Swift released her first album nearly two decades ago, and since then she’s gone on to record 10 more — earning her a total of 14 Grammys. Having attended the annual music event almost a dozen times, she’d had plenty of glamorous red carpet looks throughout the years. And looking back, her best Grammy's beauty moments show her journey from country pop ingenue to the mega star we know today. While she’s stayed true to many of her signatures in terms of hair and makeup, Swift has never been afraid to switch things up — much like she does with her music.
Swifties know all too well (wink wink) that when the singer/songwriter puts out new music, the sound is just one element of a bigger picture. From Speak Now to Reputation to Folklore and beyond, an entire mood and persona is created, and her image reflects that. Because of this, every time she steps out at the Grammys, it could just be a clue into her next era. And that’s what always makes her one to watch at the awards show year after year.
Of course the The Tortured Poets Department singer — who is up for a total of six awards at this year’s Grammys — has her favorite looks, and they can be hard to part with. For example, her the winged liner she’s been wearing for over 15 years, or her no-fail red lipstick (current fave being Pat McGrath's LiquiLUST Legendary Wear Matte Lipstick in Elson 4, FYI). But in between there’s been blunt bobs, braided updos, and metallic eye makeup that proves she’s always evolving. While you wait to see what beauty look she reveals next, enjoy a trip down memory lane that just might inspire you to enter a new beauty era.
Side Swept Baby Braids, 2024
Dressed in a Reputation-coded black and white look, Swift attended last year’s ceremony in an asymmetrical hairstyle with itty-bitty braids throughout. She also switched things up with a burgundy lipstick that’s a few shades deeper (and moodier) than her go-to red.
Midnight Eyes, 2023
Just a few months prior to the 2023 Grammys, Swift had released Midnights, and her starry nights-inspired look seemed like a direct nod to her new music. As for her glam, she wore her signature blue-red lipstick with softly smoked navy eyeshadow and her hair in a top knot with blunt bangs.
Petal Pink Makeup, 2022
The Evermore singer wore a face full of soft pink monochromatic makeup with a wispy updo that created a whimsical and romantic mood alongside her flower embellished mini dress in 2021.
Banged Bob, 2016
One of Taylor’s most dramatic hairstyles to date was the sharp bob she wore to the 2016 Grammys, which she paired with a coral-colored lipstick that perfectly matched her Versace tube top.
Pretty Ponytail, 2014
To balance out the edginess of her metallic mesh Gucci gown, the Red singer wore her hair in a perky, mid-height ponytail with side swept bangs.
Crown Braid, 2013
Nominated for “Safe & Sound” from The Hunger Games, Swift attended 2013’s ceremony in a head-to-toe goddess look that included a white J.Mendel gown and a delicate crown braid.
Metallic Eye Makeup, 2012
Swift is a fan of matching her eye makeup to her ensemble — especially when it comes to her Grammys glam. And that’s exactly what the “Mean” singer did with her gorgeous gold eyeshadow and beaded Zuhair Murad gown in 2012.
Romantic Updo, 2010
These days, Swift tends to wear straighter hairstyles, but earlier in her career she defined her natural curls more often. That includes the Fearless singer’s romantic, asymmetrical bun from 2010.
Signature Cat Eye, 2009
Taylor Swift is practically synonymous with her flicked liquid liner, so it was kind of a major beauty moment in 2009 when the Speak Now singer wore it to the awards show for the very first time.
Lavender Eye Shadow, 2008
Another matchy-matchy moment, the Best New Artist nominee attended her first-ever Grammys sporting sparkling lavender (haze) eyeshadow that complemented her strapless satin gown. And what would a best-of beauty list be without her spiral curls?
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