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!

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.

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.

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.

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.

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.

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.

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.

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.

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