The Surprising Joy of Predicting Taylor Swift’s Wardrobe
All the times I correctly guessed what Taylor would wear.
You could say it’s been a week for predictions. First, I talked at length about what I envision for the next era to come. In that post, I walked you through my notes for the sound, style, and substance of what I hope for Taylor’s future album — complete with moodboards (plural!). Then, you all thoughtfully shared your own hopes for TS12 and kickstarted a conversation over in the comments.
Now, I want to look back at my own past predictions. Specifically, the ones that hit the mark. This was inspired by a reader who asked if I’ve ever been right in my fashion forecasting. Of course, I could write a much lengthier - and far funnier - newsletter dedicated to all the times I was very *very* wrong with my prognostications. We’ve all had our own version of Roses haven’t we? (if you know, you know). But I thought it would be enlightening to see those moments from my 13+ years of documenting Taylor’s style where my guesses, informed by my experience in closely following Taylor’s fashion journey, did ring true. I’ve always gone into any prediction with the objective of deepening community and encouraging conversation. The lead up to an album release, when the air is buzzing with possibilities that could take an infinite number of paths, is one of the most fun parts of engaging in fandom. It’s a collective Christmas Eve. It’s an ongoing virtual slumber party. It is these moments that remind me most of what we’re all here for: this art made by this particular artist. Being “right” is a bonus - if it comes at all. But it sure is fun on the rare occasions that it happens!
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Now, I’ll also supply an asterisk here that the following are what I consider to be personal wins. There are so many factors that need to align for a prediction post to have its fairytale moment come to life. For a 100% win, one needs to not only guess the right designer, but the right collection, the right look, and for the right occasion. The chances of hitting the bullseye that precisely? Quite a tall order! Particularly when you consider the added likelihood of a completely bespoke (aka custom) piece coming into play. Which makes any guess completely moot as the garment is crafted as a never-before-seen one of one design.
With that, here are the occasions when my guesswork came close enough where I felt a celebratory dance was warranted.
2016 iHeartRadio Awards
What I Guessed: Saint Laurent Fall 2016, Look 4
What She Wore: Saint Laurent Fall 2016, Look 20
Why I’m Taking The W: I thought we’d start off strong where I not only nailed the right designer, but also the right collection for the right occasion. In my original prediction I had noted, “This awards show will in all likelihood be the final push from Taylor for the 1989 era. As her promise to deliver on ‘80s style for this era has been somewhat lacking, I can’t think of a more appropriate time to deliver some fashion inspired by that era. Especially after recently attending Lady Gaga’s 30th where the birthday girl herself wore something from this show.” Taylor’s stylist, Joseph Cassell, even gave me my flowers for this one. What a feat! As an extra dig, this exact jumpsuit was on my list of rejects from when I was making this prediction post (so close!). A win this close? I’ll take it.
Rep Room
What I Guessed: Ashish Spring 2018, Look 16
What She Wore: Ashish Spring 2018, Look 16
Why I’m Taking The W: I actually did guess that Taylor would wear this exact look - I just anticipated it for a different moment. Specifically, on stage at the reputation Tour! My logic, as per my original prediction post, was that it would be “a cheeky reference to Taylor’s overanalyzed love life.” Instead, we got Taylor wearing it while backstage of the very same tour while greeting fans during her one of her post-show meet and greets. At the time, Ashish was a brand Taylor was wearing often. Their oversized baggy silhouettes worked well for the toughened image of the reputation era while their impeccable sequin work tapped into a forever Taylor staple: sparkles. You might remember their rainbow sequin pieces from the reputation album photoshoot or the “End Game” music video. This is a great example of Taylor building a visual identity through repetition. Repeating certain style elements, or continuously turning to a signature designer for outfits, is how one builds a recognizable, clearly defined aesthetic. To the point where it, literally, takes the guesswork out of things.
2019 Vanity Fair Oscar Party
What I Guessed: Ralph & Russo Spring 2019 Couture, Look 30
What She Wore: Ralph & Russo Custom
Why I’m Taking The W: This was another example of the right designer at the wrong occasion. But one I was particularly proud of! I originally guessed that Taylor would wear this pastel confetti gown to the 2019 Grammys. She instead wore it to the Vanity Fair Oscar party — an event she’s attended a number of times (which I’ve also broken down here on Liner Notes). There’s an effervescence and a joy to the look that fits right into the cotton candy aesthetic of Lover but that also works as a party dress, particularly as a guest. The saddest part? We never got full, high quality images of this frock in all its glory. Taylor skipped the red carpet (her boyfriend at the time, Joe Alwyn, did pose on the step and repeat) but, luckily for us, she later posted this “getting ready” photo on Instagram before presumably heading out the door.
folklore: Long Pond Studio Sessions
What I Guessed: Stella McCartney Pre-Fall 2020, Look 3
What She Wore: Stella McCartney Pre-Fall 2020, Look 3
Why I’m Taking The W: Once again - right designer, right look, wrong moment. At this time, Taylor was leaning heavily into chic outerwear by the British designer Stella McCartney. So much so that for both covers of her 2020 surprise album drops, folklore and evermore, Taylor wore coats by Stella. Based on this precedent, I had guessed that Taylor might wear this geometric print from Stella’s Pre-Fall 2020 collection for the 2020 Sundance Film Festival — an event notorious for its requisite for warm weather dressing. Instead, Taylor pulled it out while speaking to the writing and recording process of folklore during its Long Pond Studio Session special. I thought this was a smart move as it deepened her established style aesthetic for the era. With so little opportunity in the way for live performances and promotion due to the required isolation of the COVID-19 pandemic, this created a bridge between the few assets of the era that Taylor could produce. This intentional choice created a through-line between both the surface level packaging and behind-the-scenes deep dive of the album. This is of particular significance when we recall that Taylor was her own stylist during this era - conducting all her own fashion pulls, hair, and makeup - making this a time period when the distillation between her artistic vision and execution was at its purest.
2021 Grammys
What I Guessed: Oscar de la Renta Pre-Fall 2021, Look 11
What She Wore: Oscar de la Renta Fall 2021, Look 1
Why I’m Taking The W: For the abbreviated ceremony of the 2021 Grammys, I correctly guessed the designer and the occasion but not the exact look that Taylor would wear. The logic behind my choice? Taylor was a proven fan of Oscar de la Renta’s elegant, feminine pieces and I wondered if - on the precipice of winning a momentous third win in the Album of the Year category - she might reference Fearless. Not just because it was her very first AOTY win from the 2010 ceremony but also because it would be a visual opportunity to reference it as the first instalment of her re-records project. Taylor instead opted to lean into the folklorian image of a beautiful flower-covered wood nymph which played beautifully. I’m grateful that a bow detail showed up somewhere in the ensemble - if not in the form of this yellow gown’s dramatic halter bow but in the sweet ankle ties of Taylor’s Christian Louboutins.
Eras Tour Movie premiere
What I Guessed: Oscar de la Renta Spring 2024, Look 37
What She Wore: Oscar de la Renta Resort 2023, Look 6
Why I’m Taking The W: Another moment where I guessed the right designer for the right moment, incidentally another Oscar de la Renta gown, but the wrong look. But where my prediction really got it right? The styling! Originally I had suggested the look be completed with a “red lip and pinned faux bob with tons of bangles and chandelier diamond earrings … for an old Hollywood glam feel.” Check, check, and check! The other description from my original post that tickled me? “There’s just something about the flapper fringe, the sparkle factor, the vintage-esque tasseling … that screams Taylor. Perhaps because it’s [because of the] retro, Gatsby-like energy.” The thought has never been more relevant!
2025 Grammys
What I Guessed: Vivienne Westwood Spring 2025, Look 48
What She Wore: Vivienne Westwood Custom
Why I’m Taking The W: Given that Taylor’s look was custom, this truly was as close as I could conceivably get for the occasion. Between the asymmetric draping detail and corsetry, I definitely picked the absolute closest option from the runway I could. But what I was really pleased about? I once again nailed the styling! In my original prediction, I noted how “overdue” we were for an official Vivienne Westwood red carpet appearance and that I could imagine that “a pearl and diamond necklace or (gasp) a body chain would underscore the era’s aesthetic from its tour costuming while also being appropriately sensual.” Enter: A custom Lorraine Schwartz thigh chain! So much of the art of getting dressed is in the details. A look can be made or missed depending on the hair, the makeup, the jewelry, the accessories and even the posing the wearer actions on the red carpet. It’s why fashion is not meant to be static. It’s a wearable art form that reaches its full possibility when it cradles a live human form.
And now for some honorable mentions of the times when my guesses weren’t, shall we say, quite as right as I’d imagined. Hah!
For the 2014 American Music Awards, all four of my picks were of the short and sassy variety. In my post, I cited the fact that “over-the-top gowns aren’t usually the norm” for Taylor at this more laidback and fun awards ceremony. The time period, firmly at the start of the 1989 era, also took into consideration “Taylor’s latest love for cut outs, crop tops and short hemlines” in my choices. While none of my picks even came close to resembling Taylor’s final styling, I still feel like I “won” the night. Why? Well, Taylor’s ultimate wear of an emerald green Michael Kors gown remains one of my all time favorite red carpet moments ever. Naturally, because of its greeeeeeeeen hue. It’s proof that sometimes reality can be better than what we imagine and there’s a joy to being wrong and simply feeling grateful to be along for the ride. To paraphrase a certain poet, I was wrong but I can’t help but feel like there was nothing more right!
I once predicted an over-the-top “London Boy” number for the eventually cancelled Lover Fest performances. My predictions were replete with calls for “the cheesiest, most over-the-top and obscene reference to all things London for this.” Going on to say, “I need a caricature of Idris Elba riding a scooter blasted onto the big screens. I need Big Ben and double decker buses to hit me in the face during this performance. MAXIMUM CHEESE!” Very laugh-worthy!
It was reported ahead of the 2014 Met Gala that Taylor would be a guest of designer J. Mendel. Consequently, my choices were all ballgowns by J. Mendel (another early favorite designer for Taylor) that best reflected the signature exquisite tailoring of the gala theme honoree designer Charles James. In my prediction I correctly acknowledged Taylor would “likely be wearing a custom ballgown to properly honour the designer behind this year’s theme.” But where I went awry was that her gown of choice ended up being a pink confection by a completely different designer: Oscar de la Renta. Ten years later, that dress would go on to serve as the cover of my very own book Taylor Swift Style: Fashion Through the Eras (Psst: It’s 50% off here!). A great mistake that ultimately led to something great.
📚 Now I’m Covered In You: I wrote a newsletter that walked through the arduous (and hilarious) process of designing the cover of my book Taylor Swift Style.
Honorable Mention
“Cassandra”: It all started with a bag. Back in November 2023, Taylor was spotted out to dinner in New York City with Eras Tour opener Gracie Abrams. On her shoulder - peeking out from behind a navy coat by Gant - was a chain strap bag by Saint Laurent with the style name “Cassandra.” In my original post, I pondered whether “Taylor felt kinship to a bag that also shared a name with Cassandra, of Greek myth fame who was doomed to utter prophecies that no one would believe. The poetry of that possibility really strikes me as it feels almost assured that the next (Taylor’s Version) re-record release will be reputation - an album that of course has roots in a famed phone call gone wrong where Taylor told the truth and no one believed her. Too stretchy? Or totally plausible?”. A few months later in April 2024, Taylor included a track on her newly released Anthology album titled “Cassandra” - an ode that used the aforementioned Greek myth as a backdrop to contextualize Taylor’s experience during the reputation era. Another seven months later (and nearly one year to the day of the original candid) and I would be present at Night 5 of the Eras Tour in Toronto, ON to hear the first (and only) live performance of “Cassandra” during the Surprise Song section of the tour. Goosebumps!
I hope that dig through Taylor’s — and TSS’ — fashion vault was an interesting one. I also hope it demonstrates the depth of thought that goes into creating a prediction post and the degree of consideration I put into them. Having documented her fashion so extensively for so long, Fashion History is one of my favorite niche topics. Fashion, like all art, doesn’t exist in a vacuum. When used intentionally, as Taylor has adeptly proven she loves to do, it can be a very effective communication tool. If you’re ever interested in a particular moment in Taylor’s history you’d love an in-depth reflection on, I’d love to either hear from you using my TSS Flashback Google Form!
Love your substack page
Such a fun read as usual. I will read ANYTHING you write❤️🔥