Taylor Swift's Style Evolution
From country princess to global sensation, Taylor Swift's style has evolved as much as her music. Here’s a breakdown of Swift's style over her 15 year career.
by : Heather Taylor-Singh- Dec 13th, 2021
In celebration of singer Taylor Swift’s 32nd birthday, we’re taking a trip down memory lane. Since Swift’s debut in 2006, she has had her fair share of fashion eras. From a country cutie with untamed curly hair and cowboy boots to a pop superstar taking over the music industry, she’s no stranger to a transformation. Most recently, she’s settled into a dreamy cottagecore aesthetic with sister albums, folklore and evermore – but for how long? Here’s a breakdown of Taylor Swift’s style throughout her career.
Academy of Country Music Awards, 2006
At 16 years old, Swift made her red carpet debut at the Academy of Country Music Awards in 2006. She’s wearing a floral halter dress from the BCBG Max Azria’s Spring-Summer 2006 collection with metallic cowboy boots, while rocking her blonde curly locks. This era of Swift’s style quickly earned her the nickname “America’s Sweetheart”—and rightfully so!
Grammy Awards, 2008
Swift’s first Grammy Awards was something to be celebrated. While she wasn’t nominated for any awards, she was a presenter. For music’s biggest night she sported a floor-length purple gown from Sandy Spika that features blue sparkly flowers on the lower half. It feels a bit more mature than her previous looks, but it’s still playful—especially with her bouncy curls.
MTV Video Music Awards, 2009
This night at the VMAs was memorable for a few reasons (think Kanye), including her many wins for her sophomore album, Fearless. Another reason was this sparkling Kaufman Franco toga-style dress. The one-shoulder moment feels extremely cool-girl, as Swift seemed to start experimenting with her style.
American Music Awards, 2011
Continuing in the trend of sparkly dresses, this gold strapless one from Reem Acra’s Spring 2012 collection is elegant and dainty. Paired with Swift’s straightened mane, she’s paying homage to classic glamour.
Street Style, October 2012
During the Red era of her career, Swift completely ditched cowboy boots and floral dresses in her everyday look. Instead, opting for stripes and polka dots, and of course, her ever-so-chic Charlotte Olympia cat flats. She wore very sophisticated silhouettes, replicating the retro styles of the 1950s. This mustard yellow cardigan, burgundy sweater top, navy polka dot pants combination embodies that—along with her pearl necklace which adds a layer of femininity.
MTV Video Music Awards, 2013
Paired with Swift’s curly up-do, this slinky navy dress from Hervé Léger by Max Azria is showstopping. Instead of going all out with a glittery number, this time it’s more subtle, with matching navy jewels sewn on the bodice of the dress.
Victoria's Secret Fashion Show, 2014
Strutting down the runway while singing tracks from 1989, Swift debuted at the 2014 Victoria Secret Fashion Show in a black bra top and high waisted shorts, which was layered under a lace overlay that extended into a glittery train that pooled at her platform heels. It doesn’t get sexier than this for Swift.
Throughout Swift’s 1989 era, she played with more mainstream feminine styles like crop tops and mini skirts. This black and white striped matching set from Alice + Olivia effortlessly showcases her newfound style. She levels it up with a mustard yellow Dolce & Gabbana shoulder bag and bubblegum pink Christian Louboutin heels.
MTV Video Music Awards, 2015
Continuing with the two-piece sets, Swift, who showed up with celebrity gal pals Selena Gomez and Cara Delevinge, pulled out a daring look for the 2015 MTV Video Music Awards. The jeweled toned houndstooth set by Ashish is a statement that feels very 90s. Paired with a dark cat-eye look, Swift shouldn’t be messed with.
Grammy Awards, 2015
Swift’s colourful red carpet style is once again on display at the Grammys—this time in 2015. This turquoise glitter gown from Elie Saab, looks like a modern princess moment with its high-low cut. She paired it with magenta platform heels, which is an expected colour combo, but on Swift, it works.
Met Gala, 2016
With bleached hair and a bold berry lip, Swift’s 2016 Met Gala look is arguably one of her most distinct style switchups. Serving as co-chair at the gala, Swift brought a strong contender for the Manus x Machina: Fashion in the Age of Technology theme. Wearing a custom Louis Vuitton silver snakeskin cutout dress with a pair of gladiator heels, Swift’s edgy look was seemingly a precursor to her next album, Reputation.
American Music Awards, 2018
Before her folklore track “mirrorball,” Swift was literally a disco ball in this Balmain mini dress and pair of knee-high boots at the American Music Awards in 2018. Her messy bun and retro shaped earrings tone down the look, but we can tell Swift and her stylist had so much fun planning this reflective red carpet moment.
Billboard Music Awards, 2019
Entering the Lover era, rainbows, glitter and frills were very popular in Swift’s style. This lilac frilly lace mini dress by Raisa & Vanessa is so feminine and sweet—it’s a welcome change from the dark, moodiness of the Reputation era (although both eras are incredible.) Paired with matching strappy heels, the only emotion we feel when looking at this dress is joy.
Grammy Awards, 2021
Channeling the cottagecore vibes of folklore (which won Album of Year) at the 2021 Grammy Awards, Swift is wearing a mini dress from Oscar de la Renta that’s completely decked out in flowers of every shape, size and colour. It’s another joyful look for Swift, that’s paired with light pink heels and light pink eyeshadow to match.
All Too Well: The Short Film Premiere, 2021
While celebrating the release of Red (Taylor’s Version) and All Too Well: The Short Film, Swift is sporting a maroon velvet suit from Etro’s 2020 fall collection. With a simple updo and plain black boots, the look feels extremely chic and sophisticated—Swift is channeling the intelligent businesswoman we know she is.
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