Unpacking Taylor Swift’s Style: Past, Present, & Future

With nearly a quarter of a million devoted Taylor Swift fans and fashion girlies following her on Instagram, plus a blog and an upcoming book titled Taylor Swift Style making waves, Sarah Chapelle’s love of the record-breaking Grammy winner and her ever-changing aesthetics transcends that of your average Swiftie. The 31-year-old is a writer from Vancouver, Canada, whose first listen to “Our Song” would eventually spark the creation of a platform that goes beyond typical fan fodder.

Chapelle describes her 12-year journey highlighting Swift’s every look as “critically kind fashion commentary,” though she doesn’t have a formal background in fashion. “I’m just a girl with a passion and a strong Wi-Fi connection, living the dream,” she tells Elite Daily.

If you’re familiar with her IG posts, which often arrive in her followers’ feeds mere minutes after the “Is It Over Now?” singer steps outside, you know Chapelle has a gift for writing about clothing. Her in-depth analyses of Swift’s outfits are almost as poetic as the pop star’s lyrics.

What you see as a result is a combination of years of practice and endless research.

“I spend hours looking at the latest runways, keeping up with fashion events, and familiarizing myself with the brands that Taylor reliably loves and wears,” she says. “What you see as a result is a combination of years of practice and endless research.”

While the content creator delivers her opinions on Swift’s style choices, they are contextualized within the moment and considerate of what Easter eggs she might be leaving for her fans. Chapelle’s most opinionated posts (aka the ones with ’fit descriptions that hit the caption limit) are the ones that give her the most pride — and those are usually the same posts that resonate most strongly with her followers, garnering the most likes, comments, and overall engagement.

If you’re curious about the “Karma” crooner’s recent foray into Reputation (Taylor’s Version) looks, her Chiefs game-day attire to cheer on boyfriend Travis Kelce, or anticipating the forthcoming costumes on the international leg of her Eras Tour, Swiftie style expert Chapelle has some ~thoughts~ on where Tay’s aesthetic is headed this year.

The following interview has been edited for length and clarity.

Elite Daily: We’re in the midst of your self-dubbed Roman Empire: Taylor Swift in green. What does the color signify to you?

Sarah Chapelle: I have loved seeing Taylor in green almost as long as I have been running the blog for. I have always personally coded her debut album to be more of a teal-green, which she hasn’t really been seen in lately.

One potential theory for Taylor’s recent green outfits reminds me of what a lot of fans were theorizing last fall, when Taylor’s outfits alternated between blue and black as she headed into a recording studio. It’s definitely possible that she’s cluing us into the fact that, while 1989’s signature era was associated with blue, her studio forays were to record the forthcoming Reputation (TV), represented by black. [Mind you, this was before anyone knew of The Tortured Poets Department.]

So, if we want to continue that alternating theory, that could certainly be a spillover into this year.

ED: Besides the colors, what are the most obvious Easter eggs you can point out in recent history?

SC: I think the clearest and most transparent were her Jimmy Choo x Jean Paul Gaultier boots she wore on Jan. 10.

The boots share a similar font style with what most people would recognize as being from the Reputation album, and they also obviously feature snakes coiled around the top of the boot shaft. When you pair it with an undeniably snake-like velvet green dress, it feels like a green flag, if you will, for Reputation (Taylor’s Version).

ED: Swift’s football fashion is also having a moment. What’s your take on her Chiefs game style?

SC: I think these sportier pieces really only truly make sense in the context of where she’s wearing them. We’ve seen her in the past wear athleisure looks when she’s entering and exiting gyms, in workout gear like leggings and sneakers. But her attendance at Chiefs games really does feel like a fun new exploration of her style as a proud and excited spectator who wants to dress the part.

Obviously, there’s an added layer of the other players’ significant others and kind of joining their pre-existing world of fashion. The players themselves, as well as the partners of the players, often match on game day. It’s like a team spirit thing, which I think is fun.

ED: Taylor’s also recently taken to the miniskirt trend. Do you think this is a reference to her sartorial history?

SC: Taylor’s worn and loved miniskirts over the years of her fashion evolution. I think it speaks to one of her consistent core fashion tenets, which is traditionally feminine.

She’s worn plaid and schoolgirl-esque minis, which have been mainstays since her younger days, and skater silhouettes coordinated with matching crop tops in the heyday of 1989 — and then even into Reputation, when we saw her wear miniskirts in camo, distressed denim, or army green with shirtwaist detailing.

ED: What do you think about the brands and designers she’s been wearing lately? Any theories?

SC: Taylor’s recently taken to wearing a lot of pieces from The Row, Mary-Kate and Ashley Olsen’s brand known for timeless takes on quiet luxury. Given the twins’ reclusive nature, and the fact that The Row was branded intentionally as a desire to place the focus on the fashion (aka the work and not the famous names behind the brand), I can see how that ethos might resonate with Taylor. Right now, she’s going about reclaiming a large portion of her work and defining success in her music.

ED: And her moments in platform Oxfords?

SC: Platform loafers and Oxfords are a very familiar shoe silhouette that Taylor’s worn and loved since she started incorporating vintage and mod pieces into her style circa 2010. Her relationship with heels, though, really came into being around 2008, when the heel replaced the cowboy boot as her favorite shoe of choice.

In the past, she said it was empowering to grow to love a heel, because she used to be insecure about emphasizing her height. [She’s 5-foot-11.] To me, heels symbolize a person who feels comfortable and confident in themself, and who’s unafraid to quite literally take up space. I think that’s been transformative for her as she progresses through her career, becomes more and more famous, and grows confident in not just herself, but her fashion and style.

ED: What other types of silhouettes do you think we’ll notice in her wardrobe throughout 2024?

SC: I expect we’ll continue to see costume variations pop up on the Eras Tour when she returns to the stage in Tokyo this month, and I look forward to dissecting how she plans to modernize, but also honor the original photo shoots for Reputation and her self-titled album when their respective re-recorded versions are announced.