Taylor Swift’s style eras are as distinct as her albums — meet the Canadian documenting every outfit

Almost exactly 13 years later, and under a month out from the first Toronto Eras tour stop, Swift is the biggest pop star on the planet, several lifetimes away from doing department store step-and-repeats to hawk a $60 fragrance. As for Chapelle? That post grew into Taylor Swift Style, a “critically kind” corner of the internet where she IDs and commentates on every single item the artist wears to an audience of over 339K on Instagram alone.

This fall, Chapelle has turned those years of outfit analysis into a new book, “Taylor Swift Style,” a compendium filled with details that might surprise even the most seasoned Swiftie. Case in point: Some of the first gowns a teenage Swift wore on red carpets were made by her record label founder’s wife, a demonstration of just how “in the family” her early days on Big Machine were. It underscores how painful it must have been when, as Swift sees it, they betrayed her by selling her master recordings, which eventually led to her record-breaking Taylor’s Version re-recordings of those “stolen” albums.

“I started this blog as an intersection of my most primary interests: I’d already been a fan of Taylor’s music, and I was interested in style,” said Chapelle by phone from her home in Western Canada. “Particularly how as young women, we typically use fashion as an experimentation tool to carve out or figure out our identities.”

Like so many fans, Chapelle’s connection to Swift and her music is enmeshed in the fabric of her own life. Going back through the archives of her blog while writing the book felt like getting reacquainted with both Taylor’s and her own past selves.

“I can remember where I was, and even what I was wearing, the first time I saw the Red album announcement; she was wearing this scalloped, striped Anthropologie dress. I remember where I was when the ‘Look What You Made Me Do’ music video came out: she was wearing Louis Vuitton and Gucci and Christian Louboutin, and all these custom ensembles,” said Chapelle.

For Chapelle, who works a full-time job alongside spending hours tracking down the pieces Swift wears, this passion project is a “fandom within a fandom,” a space dedicated to exploring “how Taylor’s fashion and her music work in tandem to communicate this message about her art and her artistry to the world.”

Chapelle believes that visual identity is like the other side of a locket, and you need to look at the two sides together to see the full picture of what Swift is trying to convey. “We’re most familiar with these confessional songs about her life, but her style is the other half of that story.”

It’s why tracking Swift’s street style matters just as much as what she wears on the red carpet. “For Taylor, who has built a business on being personal, there are shades of cross-over in all of it,” said Chapelle. “You can’t say, ‘Oh that’s just the pop star side of her,’ or ‘This is who she really is.’ There are shades of realness to everything that she does, and that’s why she is as successful as she is. Everything is painted with this brush of authenticity that resonates with people.”

 These days, Swiftian internet abounds in outfit sleuths who hyper-fixate on the smallest details of what she wears, always hunting for clues about what she’s up to next. Chapelle tends to roll her eyes at the Easter Egg mania—“not everything is more than what it is,” she says — but she also appreciates the hints Swift does sometimes drop.

“Something I’m personally proud of is that I correctly interpreted the ‘Cassandra’ Easter Egg,” she said, referring to a track on Swift’s latest album. “She stepped out in New York City wearing this white Alaia shirt dress and a navy Gant coat, but what struck me most was the bag, which was by Saint Laurent and the style name was Cassandra.”

At the time, months before The Tortured Poets Department was released, Chapelle wrote an entire post about how the name sparked her curiosity. “I wondered if she resonates with that name because of the Greek myth of Cassandra, and how during the Reputation period she probably felt like Cassandra, doomed to tell the truth and have nobody believe her,” said Chapelle. She’s referring to the period when Kim Kardashian released what would turn out to be a doctored phone call between the two of them that framed Swift as a liar and hypocrite. “Cut to April when Tortured Poets was released, we have a song called ‘Cassandra,’ which is about this exact thing. Pat on my back, tip of my hat, I can retire now.”

While she doesn’t have a direct line to Swift, they have met. Chapelle was one of a hand-picked group of fans invited to a pre-listening party for 1989, hosted by Swift at her New York apartment. “She’s everything you would dream and hope,” said Chapelle, who also got to hold one of Swift’s famous cats.

She may be an author now, but Chapelle will always be a fan first. “I’m three years younger than her, and I feel that at every juncture in my life, there has been a Taylor song for it,” she said. “I’ve had the immense privilege of growing up in the ripples of her wake. My life would not look or feel the same, I wouldn’t understand it the same, and it certainly wouldn’t sound the same, without her music.”

Here, Sarah Chapelle’s guide to each of Swift’s distinct, album-defined style eras.

“She was a youthful country singer who had a very clear elevator pitch in the form of a look that communicated she was a teenage girl who sang country music. The quintessential outfit is a sundress and cowboy boots, like the BCBG Max Azria dress she wore to the 2007 Academy of Country Music Awards.”

“A more romantic and whimsical wardrobe, this is when we started to see a huge injection of sparkles and slow introduction of heels. There were a lot of ‘schoolgirl’ outfits when it came to street style. This was also the start of the bracelet stack, which is very funny now that we’re in our friendship bracelet era.”

“There was a slow incorporation of vintage pieces, feminine styles of the past but they feel a bit more elevated. The number one ‘Speak Now’ outfit is the Susan Hilferty halter chiffon dress from the tour. And she loved a graphic Wildfox sweater, brown leather saddle bags, headbands across the forehead.”

“This was uber-vintage, retro fifties housewife energy. Obviously lots of red, more vintage tea-length dresses, Ray-Ban Wayfarers, kitten heels. This was also the introduction of the bangs, the red lipstick and the winged eyeliner. I love the opening Red tour outfit, where she’s wearing coated leather shorts, a button-up, a hat and the red oxfords.”

“This was the big move to New York City, with matching separates like a crop top and skirt, high heels, designer handbags. It was very uptown girl en route to Bloomingdales, city chic, impeccably done. The outfit that comes to mind for 1989 is the one that set the era off, which is the marled pink Aqua co-ordinating set from June 2014. That was the first set she wore, and the second I saw that, I knew something was afoot.”

“Lots of black and camo and snakeskin, very bombastic and in your face. The top brands were Faith Connection and Aashish. The outfit that always comes to me is the Fausto Puglisi custom romper that she wore ahead of the New Jersey tour dates. It’s iconic.”

“Pastel, sparkles, rainbows, cupcakes, sunshine, tulle, tie dye, butterflies, dip-dyed hair. It was very fun and light and girly. The key designer in this era is Stella McCartney, because she had a big fashion collab with her. The outfit that kicked off this era is the Rosa Bloom romper that she wore to the 2019 iHeart Radio Awards with the Sophia Webster butterfly heels.”

“In the book I combine them into one chapter. It’s your cottage-core, literary friend who accidentally wrote a five-part novel in their spare time. It’s a plaid, ruffled Victorian blouse, gingham skirt, chunky boots. The key brands are more Stella McCartney, Magnolia Pearl and Free People. The album photo shoots are the strongest visuals from that era.”

“This is glam showgirl meets the seventies, high shine but with a dark glamour. She wore lots of vintage, Moschino, Acne Studios and Miu Miu. This is also when we were introduced to Pat McGrath’s Elson 4 lipstick.”

“It feels more elevated, sensual, vulnerable and womanly than I’ve previously seen in her style, in a way that underlines the very raw nature of the album. There are a lot of uncomfortable truths on Tortured Poets that she is comfortable exploring, saying ‘I am not a perfect person.’ That’s created a really interesting tension with her style. There are lots of bustiers and corsets, which are things that have origins as intimate wear, things you wear under your clothes but now they are the clothes.”