Taylor Swift Convinced Me to Wear Skorts Again

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Taylor Swift’s ongoing street style era has given her fans a lot to dissect. This is doubly true for me, a fashion editor and Swiftie of more than a decade.

I've followed the singer’s wardrobe evolution since I first downloaded Fearless (regrettably not Taylor’s Version) to my iPod in 2008. But I’ve been more interested in the amateur detective work that comes with listening to Taylor Swift's music, decoding the messages she bakes into her personal style, than copying any of her outfits myself. The “Anti-Hero” singer infamously hides clues about her upcoming work in unexpected places, including her necklace stack and bedazzled denim. Yet last month, I was compelled to actually buy an item out of Swift’s closet for the first time.

Between stops on her ongoing Eras Tour, Taylor Swift has been photographed in Free People skorts three times, all while visiting New York City. Twice, she’s worn the ultra-mini Heartbreaker skort (once in a denim that borders on black in May, then again in June). Third, she chose a denim wrap skort that goes by ‘Emmy.’

Skorts were not an item high on my list of nostalgic items to revisit in my summer wardrobe. Yet something about the way Swift first layered her initial Free People skort with a vintage NYU sweatshirt and sneakers from The Row compelled me to hit “Order.”

When the skort arrived three days later, I realized it was the initial styling that made me a skort convert. Swift has never been the type to walk into the studio in head-to-toe drip that’s entirely unattainable for her fans. She’s actually the ultimate appreciator of a high-low moment. Her wardrobe has lately included sprinklings of luxury designers she hadn’t worn as often in the past: several other pieces from The Row, a pair of Chanel loafers, some Cartier jewelry. She’s in her thirties and has the grown-up purchases to prove it, but she clearly appreciates finds from brands she’s worn all along like Free People, Reformation, and Dôen. It sounds familiar to me, a nearly-30-year-old who’s also making her first real investment purchases.

The skort may end up being a gateway copycat purchase. Since following Swift’s lead, my skort has mostly been the base of a throw-on-and-go outfit for running errands around my neighborhood, in a crewneck T-shirt and Staud sneakers. This week, inspired by sighting number two, I wore my skort to work from home with an oversized button-down. Instead of chunky loafers, I opted for a pair of Miu Miu ballerinas and ruffled ankle socks.

Now, I understand why a celebrity with a limitless wardrobe would wear this garment twice. It’s comfortable, functional, and ever so slightly aligned with fashion’s recent prep revival. (Some reviewers have found that the skort runs big; I actually ordered one size up from my usual. I have wider hips and wanted a few centimeters’ more hemline.) Mostly, I love that I can dress like myself in it and still ride a Citibike.

For Swift, the skort and its associated outfits aren't just an opportunity to quietly influence how her fans dress. The “Karma” singer once reflected in an interview that "going through phases" is her favorite part of fashion. "I love how it can mark the passage of time. It’s similar to my songs in that way—it all helps identify where I was at in different points of my life," she said.

How Swift’s recent skort trend will be defined in the arc of her career-long style evolution is far from decided. The Eras tour is just over halfway through its U.S. leg, with dozens of international dates stretching into next year. All these skort sightings took place in front of a recording studio–meaning they may or may not be associated with new music.

For now, for my own closet, I’ll always think of this Free People skort as a souvenir of the first leg of the Eras tour. I have a feeling I’ll wear it beyond this summer—whether or not I can secure tickets to her shows.

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