Every era of Taylor Swift's street style, ranked (2024)

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7. The "Reputation" era

When Swift reemerged from her self-imposed exile, she had strategically embraced the public's suspicions about her personality — dramatic, calculated, salacious — and absorbed them into her art. The Reputation Stadium Tour was full of snakes, satire, and over-the-top theatrics.

Unfortunately, this bled into Swift's street style in a chaotic way. Throughout 2017 and 2018, she wore a lot of loud prints and shoes with cheap-looking studs.

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6. The "Lover" era

Swift elevated her street style slightly when she transitioned from promoting "Reputation" to "Lover," trading blacks and grays for pinks and pastels.

But sadly, the busy patterns stayed put. Even though florals are better on Swift than animal prints, it's still not her best look.

Swift also wore a lot of shiny fabrics and sequins in 2019, which were fun and nostalgic, if a bit on the nose.

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5. The teen years

Throughout her first few years in the music industry, making a name for herself in Nashville and beyond, one could describe Swift's style as girl-next-door whimsy.

Of course, she was still very young at the time; Swift was only 16 years old when she released her self-titled debut album in 2006. Fittingly, her everyday outfits tended to be cozy and feminine: think baggy sweaters, flat shoes, and sundresses.

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4. The "Red" era

Swift thankfully wasn't trailed by the paparazzi much during her teen years, but she became a tabloid fixation during the "Red" era, presumably fueled by public outings with stars like Dianna Agron and Harry Styles. (Photographers love a two-for-one celebrity deal.)

In those days, Swift preferred a sort of '50s housewife vibe, often donning knee-length A-line skirts, polka dots, and flimsy little cardigans. Her outfits were almost emphatically uncool, but that's why they worked. In those days, part of Swift's appeal was that she cared more about staying earnest than being trendy.

Particularly in late 2012, around the release of "Red," Swift's street style also had a distinctly autumnal vibe — which complimented the album's sound beautifully.

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3. The alleged "Karma" era

According to Swiftian lore, there is a lost album from the time between "1989" and "Reputation," which some fans are convinced was meant to be titled "Karma."

Whether or not this fabled album was actually recorded in 2016, one thing is for sure: Swift was serving looks that year.

After Anna Wintour convinced Swift to chop and bleach her hair for the cover of Vogue, the singer began experimenting and deviating from her typical style. She showed up to the Met Gala wearing black lipstick and donned leather jackets to prowl the streets.

This is a version of Swift we had never seen before, and are unlikely to ever see again. ("Reputation" may have been an attempt to recreate it, but ended up feeling more kitschy than badass.)

The platinum-blonde bob is controversial among Swifties, but for my money, it inspired one of the most exciting transformations in Swift's career. If "Karma" exists, I bet it's a rock-infused fever dream.

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2. The "1989" era

In late 2014 and through 2015, Swift was all about sleek lines, miniskirts, checked prints, and pops of color.

She had recently moved from Nashville to New York City and pivoted from country to pop with "1989," her showstopping fifth album. Naturally, she adopted a personal style to match. Her outfits were polished, mature, and, dare I say, iconic.

Maybe you had to be there — with "Blank Space" blasting in every grocery store, paparazzi photos of Swift plastered on every magazine cover, and even the most stubborn skeptics humming "Shake It Off" in the check-out line — but it felt like the start of something huge. And it was.

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1. The modern "Midnights" era

Swift's personal style during the "Midnights" era has been dominated by baseball caps, chunky shoes, and relaxed silhouettes so far. She has also been favoring neutral colors (black, white, navy) and chic basics.

In between stops on the Eras Tour, Swift has been photographed in New York City (typically coming and going from the recording studio because she hates to sleep, I guess) rocking outfits that prioritize comfort, yet still exude a sense of power.

During one concert, Swift told fans that she's "never been this happy." She has also described the Eras Tour as "the most meaningful, electric experience of my life so far."

This contentment seems to have sunk into her aesthetic; there is a unique power that comes from feeling free, fulfilled, and confident in your own skin.