How to Decode Taylor Swift’s Style, From Backward Outfits to Reputation Red Herrings

Getty Images; Design by Channing Smith

For fans in the know, decoding a Taylor Swift outfit is nearly as thrilling as parsing her lyrics or Instagram captions for clues. The cryptic queen leaves subtle (and not-so-subtle) messages everywhere (remember five holes in the fence?)—so why not her clothes too? With stage-managed pap shoots and unmarked sponcon more prevalent than ever among celebrities, Swift clearly knows that people will pay attention to what she’s wearing.

Fashion has become its own vertical in Swift’s universe, with The Cut asking “why Taylor Swift Dresses Like That” while The Independent chalks up interest in Swift’s style to sexism. By any measure, Swift is gorgeous and stylish. But in the hypercompetitive and appearance-obsessed strata she inhabits, there is no room for error…and Swift apparently errs so much that a certain corner of the internet has branded her Allergic To Serving. There is even an Instagram account dedicated to Photoshopping her into more fashion-forward looks, and you can find accounts like the self-described Swiftologist “brutally reviewing” both her street style and red-carpet looks on YouTube. (For my money, the most objective overview of her fashion journey is from the always excellent account ModernGurlz.)

To gain a deeper understanding of both Swift’s fashion sense and how she positions herself within the broader style discourse, I spoke with the only woman who may know Taylor’s style better than Taylor herself: Sarah Chapelle, the creator and operator of @TaylorSwiftStyled and author of Taylor Swift Style: Fashion Through the Eras, which hits shelves this October. Tl;dr she’s the one who found all the Tortured Poets Department clothing Easter eggs.

“Taylor Swift Style is the definitive Swift style Bible,” Chapelle tells me. “It tells the fashion story behind every single Taylor Swift album and her musical and sartorial evolution, and it’s based on my own content archives and extensive research, accompanied by over 200 photographs of Taylor’s most fashionable moments.”

Like Swift herself, Chapelle is thorough and eagle-eyed…some might say a fanatic. She writes long, thorough captions to help followers interpret Swift’s clothes and patiently answers questions about all things Taylor from an educated, not a stan-crazy perspective. Most helpfully, she finds affordable dupes for many of Swift’s items. Have I purchased boots worn by Taylor and identified by Sarah? No. But I asked for them for my birthday.

Just before the release of TTPD, Chapelle and I caught up over Zoom. And Tree Paine, if you’re reading this, please take her words seriously. She knows what she’s talking about.

Glamour: What is your process? Do you have Google alerts when Taylor gets photographed? How does a person run a Taylor Swift style account and identify all this stuff?

Sarah Chapelle: I follow a lot of really awesome update accounts. There’s Google alerts, there’s tweets that come through, and even good old-fashioned Swiftie group chats. In terms of my process, I’ve been running @TaylorSwiftStyled for almost 13 years now, so I have it down to a science and an art. There are a lot of brands that she continues to return to…so when she’s out and about, it’s easy to decipher, like, “Oh, that fit and flair cut and that particular color looks like a Reformation dress.” Or, there’s a certain cut of denim or trendy silhouette that indicates it’s probably Free People. And so begins the process of combing through all of these different retailers’ websites until I find the exact match.

What I hope is the extra something that I bring to the table is the power of the caption and being able to contextualize what a clothing choice means in the Taylor Swift cinematic universe. What does this bag represent? Maybe the last time she carried it was like 2014, and that’s a worthwhile thing to bring up. She’s the type of person who loves to repeat things and recycle accessories. That repetition is something that fans resonate with because it’s like, “Ah, someone else who gets their cost-per-wear down by re-wearing and repeating pieces in their closet like a normal person.” It’s sad that’s notable as a celebrity, but the fact of the matter is that, yes, it’s notable.

So then, how do you think she gets dressed in the morning? I wouldn’t put it past her to be sitting there with a grid of: “When was the last time I carried this bag?” Or do you think she has someone in charge of that?

I suppose it’s an open secret that most celebrities, even in their daily lives, are intentionally styled, and Taylor does have a style team. However, I do think Taylor has uniquely positioned herself as the arbiter of her public image and somebody who cares very deeply about the intention in which she shows up in the public eye. As a medium of communication, her fashion is a tool that she likes to wield and utilize. Whether that means distinguishing eras over the course of her career or sending red herrings to fans to drive them into a frenzy. We now know that the usage of green earlier this year, pre-Grammys, and even the Jimmy Choo, Jean Paul Gaultier collab boots that she wore that had snakes on them, were an intentional misdirect hinting at Reputation TV. Which was very tricky of her.

But in terms of how she ends up getting dressed, I feel like this is a Cher Horowitz-meets-“Mastermind” situation where one can barely fathom the depths of her closet and how she goes about intentionally or passively selecting what she chooses to wear that day.

How much jewelry does she own versus what is lent to her? Does this apply to other pieces of her wardrobe?

Based on my knowledge of the industry and how it typically works, I assume that most of her red-carpet jewelry are loans. I also assume that many of her outings are styled with smatterings of personal pieces that she herself has acquired. I know it seems farfetched, but I do think she actually does a small amount of shopping on her own, which I think is a key part of her appeal. That quirk factor to her outfits. The personal whimsy she sometimes brings to her styling.

A lot of celebrities at her level have contracts with certain brands, though mostly it’s actors who do a lot of red carpets. Taylor has the freedom to wear Chanel one day and Prada the next day. Has she ever really picked a brand or partnered up with a designer?

Not to an explicit extent where she’s a contracted ambassador for a brand. So there’s a certain, I guess, authenticity to what she wears, wherein she will just simply wear what speaks to her. I love that, whether that’s a Gucci bag or an Urban Outfitters top, it’s whatever speaks to her that moment. I think that’s very admirable and cool.

We know that she does have fashion connections. Stella McCartney is a notable one—she’s gone so far as to name-drop Stella in her music, and she did the Stella McCartney merchandise line for Lover.

It’s funny you mentioned Gucci. While I was looking through your book, I thought, “She should only wear Gucci.” Every time I thought she truly hit the nail on the head, that was the brand.

There’s been so many instances where I have discovered that my sweet spot for Taylor is the Gucci column gown. It’s fantastic on her.

In terms of future brand ambassadorships, I strongly feel like the brand that would “get” her the most is Ralph Lauren. She’s carried many, many Ralph Lauren bags over the course of her career. As a brand, from an ethos perspective of tapping into that sense of everyday Americana luxury, that definitely feels very Taylor and could be really cool.

Speaking of partnering up with designers, do you think she’s going to go to the Met Gala? She doesn’t have to perform again until the ninth and it’s on May 4.

She technically has availability in her calendar to go. It’s whether she wants to prioritize attending that is kind of up in the air. I can understand why she’d want to go to Coachella because even though that’s a very public event, she’s able to hear live music, enjoy herself, feel freedom and fun, and go out and support her friends who are performing. But what does the Met Gala provide for the world’s most famous superstar at this point in time? That’s the question. I would love if she attended. Love it.

Moving onto some of her more questionable sartorial decisions, what do you make of her wearing stuff backwards? Because she’s done it a number of times. That’s got to be her decision, right? No one’s telling her to do that.

The fact that I have enough posts to fill a dedicated tag on the blog with pieces that she’s worn backwards is very amusing. She approaches her style with so much intentionality, but I don’t think these were instances of her wearing things backwards with intention. I think they were just very comedic oopsies.

You think she thought she was wearing them the right way?

I mean, who hasn’t experienced getting to the end of the day and realizing that your shirt is on backwards? Again, speaking to the relatability that is Taylor Swift; who has not, at one point in time or five points in time, experienced accidentally wearing something backwards?

What do you say to the discourse among non-Swifties that fashion is one area where she’s weaker? Even as a fan, I don’t think of her as super fashion-forward—but it’s okay because she’s not trying to be. She’s so good at almost every other aspect of being a celebrity.

Generally speaking, what draws people to Taylor’s fashion is not for looks that challenge trends or push the needle, and that is okay. I mean, Taylor Swift made headlines when she cut her hair into a bob. That was a huge, earthquake-level change in her cinematic universe. Compared to most celebrities, who often dye their hair between every other project or cut bangs or change their hairstyle on a whim, that was a magnitude-level shift that indicated a huge change was happening.

How would you describe her Tortured Poets style? I’m having trouble separating it from her WAG style, and I feel like it’s notable that she’s been actively wearing another person’s brand and advertising for Travis and the Chiefs with her clothes.

This is possibly the first time for an album rollout where there hasn’t been the anticipated volume of aesthetic output in relation to that era’s established aesthetic. This is probably the least amount of era-aligned outfits that we’ve had in the lead-up to an album, which is very interesting.

There is a “tortured poets” aesthetic that is very Dark Academia, literary, kind of like a more elevated version of the schoolgirl outfit accessories that she’s liked for a very long time. There are many instances from Fearless to Speak Now, and even into 1989, where Taylor loves a heeled loafer. She loves a pleated, flippy plaid miniskirt. Even in the 1989 era, she loved a knee-high sock. These aren’t necessarily new items for her to be wearing, but the way that they’re packaged in this poets filter feels a little bit more tortured, a little more anguished and dark and introspective.

This distinction between the few outings that we’ve had in contrast to the album is a subconscious reminder of, “This is what I went through, and I’m thankfully not in that place right now. So bear that in mind when you listen.”

If you’re speaking to a casual fan, someone who watched The Eras Tour on Disney+ but didn’t go in person, what would you say are the beginner level things to look out for when analyzing a Taylor Swift outfit? Do they all have Easter eggs, or are we just looking at vibes?

The most important thing to know is that context matters. You can’t really analyze her looks within an isolated bubble. You need to understand where she is and why she’s there. I don’t think that you can look at her Coachella outfit, for instance, and find out much about her intentional approach to style. You need to understand that she’s at a music festival with her boyfriend to support her friends. It’s most likely that she’s seeking comfort, function, cute festival vibes, and there’s not much to pull apart there. Sometimes there may not be a meaning beyond the logistical requirements of that day.

If you could give her one piece of style advice, what would you say?

If she still has that green Ellie Saab bag, would she consider giving it to somebody who is a great admirer of it?

Which other celebrities are you following stylewise? Is there anyone you pay as much attention to?

I don’t pay this much attention to anybody else. In terms of celebrities whose fashion I have enjoyed watching as of late, Zendaya obviously comes to mind. Carey Mulligan’s recent award season was like chef’s kiss perfect for me. I loved watching that unfold. Blake Lively is always fun to watch. I really like Meghan Markle, Duchess of Sussex’s personal style. I like pretty much everything that Meghan wears.

If you had to describe Taylor’s style—in this current era, that is—what three adjectives come to mind?

Feminine, thoughtful, relatable.

Until her next reinvention.

Elizabeth Logan is a writer in Los Angeles. You can follow her on Instagram at @lizzzzzielogan if you don’t mind cat pictures.

Originally Appeared on Glamour