The Moments I Knew: Taylor By the Eras, A Fashion Timeline
The Moments I Knew: Taylor By the Eras, A Fashion Timeline
A peek into the context, commentary, and pretty photos in my book Taylor Swift Style
By its subtitle, I’m sure you can imagine that Taylor Swift Style is a journey through all of Taylor’s eras. I wanted to write a book that definitively captured both her musical and sartorial evolution and demonstrated how the two work in tandem to communicate a message from one of the savviest pop stars of our modern age.
Today, I wanted to pull back the curtain on a few of the looks from Taylor’s life to map them on a timeline of moments from when I “knew” something different this way was coming.
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Fearless > Speak Now. May 19, 2010
At this junction, Taylor was on the cusp of completing the Fearless Tour (its final date would be just a month later in June 2010). The fashion between Fearless and Speak Now are often where lines get the blurriest for people, even myself. They both are anchored in a girlish sensibility of clothing, inspired heavily by the whimsy of fairy tales. But there were a few key departures in terms of accessories, colours, and fabrications.
For me, the tipoff here was the headband placement. I like to call it a “forehead belt” if you will. Plus we’re clearly starting to push into the later-aughts/’10s trend of unnecessarily belting random items. The swap from a peep toe platform (something she started to wear during Fearless in favour of her previously loved cowboy boots) to vintage-looking Chelsea Crew character heels also tells a lot. Lastly, hindsight gives us the gift of clocking the Speak Now purple of her tiered Free People skirt. The skirt, especially, feels like you could draw a direct line from it to the fluffy, tulle Giambattista Valli confection on the Speak Now (Taylor’s Version) cover, right?
Taylor herself described the Speak Now album as one written primarily on the road when she didn’t have any co-writers at her disposal. “It didn't really happen on purpose, it just sort of happened. Like, I'd get my best ideas at 3:00 am in Arkansas, and I didn't have a co-writer around and I would just finish it,” she once described to The Boot. While perhaps we always knew, we certainly know now that Taylor rarely does things without a purpose. In 2019, she would clarify during her Billboard Woman of the Decade speech that part of her entirely self-written efforts was in response to sexist lines of questioning that someone that young and that girlish could not possibly be writing her own songs without serious assistance from more experienced pens. “All of a sudden they weren’t sure if I was the one writing the songs because sometimes in the past I had had co-writers in the room … I decided that I would be the only songwriter on my third album, Speak Now … I decided I would be what they said I couldn’t be.”
Speak Now > RED. March 19, 2012 + May 28, 2012
Besides the moments captured of Taylor with Conor Kennedy at the sprawling Kennedy Compound in Hyannis Port, MA engaging in wholesome moments of ocean frolicking in ruched one-piece swimsuits or strolling along sidewalks in demure vintage dresses, there were a few other tip offs through the spring of 2012 that something different was coming.
The ones that stood out most to me were the two below.
The first, a cap-sleeved rose-print dress by Australian-designer Alannah Hill. Taylor had quite literally just completed the Oceania leg of the Speak Now Tour. The colours, the mod silhouette, the string of pearls, the French Sole velvet loafers all seemed new to me. While Taylor had certainly begun dipping her toe into vintage or vintage-inspired pieces during the Speak Now era, it’s RED that really became known for its retro “grandma” styles. In her 2022 NYU Commencement speech, Taylor said, "I had a phase where, for the entirety of 2012, I dressed like a 1950s housewife. But you know what? I was having fun. Trends and phases are fun. Looking back and laughing is fun." I also thoroughly enjoyed the diplomacy on display here, giving a final tip of her cap to Australia by wearing a design by one of their talents.
The second is this recording studio outing in May 2012. Besides the fact that Ed Sheeran was spotted in Taylor’s tow leaving the studio so we can now piece together that this was the day when “Everything Has Changed” was recorded, I wanted to draw attention to some of the key retro pieces on display here. Note the continuation of the aforementioned French Sole loafers from the Australian airport look. I also had to laugh at my original caption: “Two important things to note here. First: check those pants. Vintage indeed! Second: Album IV is still under way.” Album IV! GOODNESS! The polka dot cigarette pants did indeed feel very vintage to me. But perhaps most iconic of all? Those Ray-Ban Wayfarers, of course.
RED > 1989. June 18, 2024
In Taylor Swift Style (Book Version), I call this “the look that launched an era.” There’s a generous caption for this look in the book, so I’ll keep it short and sweet here and say that still to this day, it’s one of the clearest era kickoff looks that I can recall in my memory. Everything about this screams new and interesting and different. We had never seen Taylor dress like this previously.
The tops were cropped. The heels were sky high. The move to New York proved to be a major catalyst for the style and sound of the era to come.
1989 > reputation. February 24, 2016
I appreciate that in my original post for the Vetements boots she is wearing in this photo that I specifically called out how the dress itself might not be weird from Taylor - but the styling was. I even mentioned other pairs of shoes we might have typically, previously expected to see Taylor wear. Including a pair of Louboutin heeled oxfords or what I called her “standard” pair of simple, Rag & Bone ankle boots
Suffice to say, when we saw this all black look set off by a chunky pair of boots and a coconut bob that we knew something was up. In fact, when Taylor’s May spread with Vogue came out a few months after this in which several shots included these very same Vetements boots which she nabbed from the set I said, “I should have known after seeing these shoes that they were indicative of something Much Bigger going on behind-the-scenes for Taylor’s TS6 fashion.”
It’s worth noting though at this point in Taylor’s career she was soundly between projects and in a self-described point where for “first time in ten years” she hadn’t known what was “next”. At the time of this outing, she’d just put the 1989 era to bed a little over a week prior when she won Album Of the Year at the 2016 Grammys. So was this an intentional nod to an aesthetic to come? Or the low-stakes experimentation period she was seeking when she “decided that after the past year, with all of the unbelievable things that happened … I decided I was going to live my life a little bit without the pressure on myself to create something.”
reputation > Lover. March 14, 2019
As context, we were a few weeks fresh from Taylor’s cryptic palm tree post on Instagram which many (correctly!) interpreted as a “tease” for “TS7”. Proving that Swifties are like a broken clock - right twice a day. The stage was also set by Taylor’s Elle spread for April 2019. In it, she wrote a personal essay about the lessons she learned as she approached turning 30 while also not-so-subtly dropping lyrics in her captions with photos from the spread. By the time we got to the iHeartRadio Awards, the fanbase was primed for Easter Egg tomfoolery.
The butterfly Sophia Webster heels were the clear Egg on display here (which also got a cryptic mention in her Instagram caption from the day wearing a Gucci cardigan). The colour palette on her Rosa Bloom romper would become the basis for the technicolour pastel world of Lover.
evermore > Midnights. August 28, 2022
I typically require time to write my captions. It’s important to me and pivotal to the entire ethos of TSS that I give each look the same level of care and thought when analyzing them as Taylor does when crafting the image to communicate. With that in mind, I had the gift of being able to write my caption of Taylor’s diamond drip Oscar de la Renta dress worn to the 2022 MTV VMAs post-announcement of Midnight’s impending release.
That said, I can vividly recall seeing this dress and - amidst the comparisons to the diamond bathtub scene in the “Look What You Made Me Do” music video - remarking how different everything about the look felt. “This is a sartorial step in a fresh, new direction to reflect a new body of work and a new period in her life,” I wrote.
It set us up for an aesthetic that was dark and glamorous. As shimmering, ruminating, and captivating as the album that would follow.
Midnights > The Tortured Poets Department. February 4, 2024
If this fandom had a nickel for every time Taylor attended an award show thinking we would get reputation (Taylor’s Version) but we got a new album instead, we would have two nickels. Which isn’t a lot but it’s weird that it happened twice.
When Taylor appeared at the 2024 Grammys in custom Schiaparelli, many immediately began drawing comparisons to reputation. But this was one instance where - again - things felt distinctly different. But - again - I had the gift of having taken a beat to collect my thoughts and write a caption analyzing this look with the knowledge that The Tortured Poets Department was imminent.
In my caption I wrote, “The draping akin to tangled bedsheets, the Victorian cameo-esque appearance of the watch choker from afar, the dramatic opera gloves, the corset back, and the black and white colour scheme feel pulled from (or inspired by) what we now know is the forthcoming album formerly known as ‘TS11’: Tortured Poets Department. And if Taylor’s admission that this project has been in the works for the last two years is anything to go by, it also throws into sharp relief the schoolgirl plaids, the dark academia loafers, and the shadowy colour palette her street style has often centered on in recent months.”
I hope this post gives you a small glimpse into the level of deep research, expertise, nuance, and contextualization that I wrote Taylor Swift Style with (though of course the book covers debut through Midnights and the Eras Tour - leaving room for Poets to be Chapter 1 of Volume 2, perhaps).
The first week of sales is so vital to a book and its success. We only have a few days left to make an impact on the next bestseller list. If you’re interested in fashion history, nuanced analysis, and a definitive deep dive into the journey of Taylor’s fashion I would so appreciate your support of this book.