It seems as though, for the last few years, no autumn has been complete without a Taylor Swift release. October 2022, Swift graced our ears with her 10th album, Midnights. The following year, she re-released Blank Space, and in November 2025, her 12th album, The Life Of A Showgirl, shocked us all with its unusually upbeat sound. This fall, Swift caught the music scene’s attention once again with the drop of her last album’s deluxe tracks, The Life Of A Showgirl: The Encore.
Since its release, The Encore has completely polarized not only “Swifties” worldwide, but also much of the pop culture audience. While some listeners may have preferred the four extra songs for their catchy melodies and striking lyrics, others were disheartened by the pop star’s departure from her usual nuanced and often prophetic songwriting.Â
I can’t say I particularly loved any of the new songs, but I do know that, whether society believes it or not, Swift is truly a poignant songwriter and the voice of our generation. To remind myself just how talented she is, I’ve been revisiting some of my favorite songs of hers that are not only lyrically complex, but also carry the moody, emotional, and transformative vibes synonymous with the fall season.
After all, what amplifies fall energy more than music?Â
- “cowboy like me” – evermore
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From her ninth album, Evermore, “cowboy like me” immediately catapults listeners into a sultry autumn day with its cathartic opening piano and guitar notes. Overall, Evermore is infused with a folk music tone, which listeners can recognize through the “warm” guitar notes and occasional harmonica.
Its unmistakable folk influence, coupled with the album cover’s autumnal imagery, offers listeners a familiar sound and the nostalgic sensation of a fall day. Not to mention, some lyrics, like “the skeletons in both our closets,” nod to the inevitable collapse of the vibrancy of summer and the impending gray of autumn.
- “Dear John” – Speak NowÂ
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Nothing says autumn to me quite like the velvety strum of an acoustic guitar. Pairing that with devastatingly heartbreaking lyricism is exactly what makes this song feel like fall to me. However, the song also connects thematically to the fall season. Autumn is often regarded as a time of change, not only in the leaves but in our lives.
“Dear John” tells the story of a saddening shift in a tortured relationship, underlining how sudden and abrupt change can be. Much like the greedy hands that strip away the bright green of summer and replace it with the deepening leaves of fall, sometimes the selfish hands of time snatch one’s love in a way that feels hasty.
The lyrical journey Swift takes us on throughout this song is so reminiscent of the achy change from summer to fall.
- “cardigan” – folklore
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The title of this song may or may not hint at the comforting feeling one gets when they listen to it. That same feeling seems ever-present during the fall season.
“Cardigan,” similar to “cowboy like me,” begins with a soothing piano riff before descending into lyrics about a love that can only be described as reassuring and familiar. Masked with a melancholy melody, “cardigan” tells the story of a warm love that feels like home.
To me, being able to return to something that feels like home in a time of uncertainty isn’t just something you can experience in a relationship; it’s also something the promise of a new season can offer us. Just as people yearn for summer and a season of adventure, we can also yearn for fall and a season of familiarity, like Swift’s “cardigan” love.
- “’tis the damn season” – evermore
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“Tis the damn season” is another track from evermore, and an automatically autumnal album, as I mentioned earlier. This song keeps the same folky mix of instruments as “cowboy like me,” similarly transporting listeners into a world of fall foliage. Moreover, this track invites themes of nostalgia and familiarity that remind us of the fall season.
This song is an honest take on returning to your hometown and all of the painful relationships that come with it. With mentions of the holiday season and a chill in the air, this track feels like a crisp fall weekend in your old town — and perhaps with an old friend…
- “All Too Well” – Red
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Last but not least, there’s no Taylor Swift song that’s a truer fall tune than “All Too Well.” “All Too Well” is a quintessential autumn song, filled with lyrics like “autumn leaves falling down” and “keep my old scarf.” The fall imagery is undeniable. The song hails from Swift’s fourth album Red, which, like evermore, carries fall vibes throughout, even on the album cover.
In November 2021, Swift released a 10-minute version of “All Too Well,” exploring a depth of fall that wasn’t reached before: the season’s unfortunate end. The new edition added the line, “I still remember the first fall of snow.” The first snowfall and the descent from fall into winter are not only a poignant metaphor for the way people change, but also the distinct heaviness of the end of fall.Â
From autumnal album art to lyrics that capture the season, these five songs are just a few of the many perfect for this fleeting time.Â
No one writes fall songs quite like Taylor Swift.
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