It’s no secret that Taylor Swift and fall go hand in hand. While we’re big fans of her music year-round (duh), a majority of her albums just deliver a different listening experience when the leaves are changing and there’s a crisp chill in the air. Of course, the fact that many of her songs reference fall-oriented outfit pieces nudges that notion along too. The cardigan, a red scarf—what’s next, a chunky lug-sole boot?
If you’re finding yourself searching for outfits to fill the fall days that we have ahead of us before winter hits, it’s time to have a little bit of fun. The best way, we say? Getting inspired by pop culture. And today’s deep dive is a history lesson in Taylor Swift’s album eras—and how you can turn each into a top-notch fall look.
We put our Midnights on pause long enough to go back and listen to Taylor’s discography to figure out how to draw inspiration from each time period—both in the music’s vibe and what she was wearing at the time. With 10 albums, we’d go ahead and say you have your looks planned for the next week and a half.
Taylor Swift
cardigan (plus) | dress (plus) | boots
Believe it or not, Taylor Swift’s self-titled debut album is almost 20—yes, 20—years old. Listening to it today still holds all the nostalgia and warm feelings now as it did when you heard “Tim McGraw” on the radio for the first time (we all remember where we were). From her long, curly tresses to her true country roots, this album is pure coziness wrapped in a bow.
Fearless
bodysuit (plus)| skirt (plus)| bag | boots
Taylor dropping Fearless (Taylor’s Version) last year was actually the beginning of a huge cultural reset. Not only did she allow us to relive our favorite songs of her in slightly updated ways, but she showed us how she took control of the narrative of that time in her life. Channel Taylor’s sparkly, Fearless tour era with silver details and black accents–both of which are perfect for fall (and happen to be trending this year).
Speak Now
sweater | blouse (plus) | trousers (plus) | coat (plus)| loafers
Drop everything now. Check. Meet you in the pouring rain. Double check.
Speak Now is the ultimate album to listen to when you’re romanticizing your life—which we recommend doing every day. The best way to do that? With some purple pants and a dreamy, corset-detailed top that screams “romance”—but not in a cheesy way.
Red
turtleneck (plus) | coat (plus) | jeans (plus) | boots | scarf
The fall album that started it all, listening to Red feels the same as running through multicolored leaves or transitioning from iced coffee to hot coffee on the first day below 60 degrees. We know, we know, the scarf is a metaphor, but today we’re taking it literally, and it just so happens to be the perfect topper to casual-cool look.
1989
turtleneck (plus) | jacket (plus) | skirt (plus) | shoes | tote
1989 is all about fun, flirty, carefree vibes, so of course a mini skirt is involved. To further emulate the era, we’re pairing it with slightly twee details that make it feel undeniably Taylor.
Reputation
tank (plus) | blazer (plus) | trousers (plus) | booties
We all recognize and appreciate the term “in my reputation era,” and this outfit encapsulates exactly that. There’s never a bad time to be going through yours, especially in the fall when you can wrap yourself in all the leather you can get your hands on.
Lover
top (plus) | coat (plus)| trousers (plus) | bag | loafers
Oh, Lover. This album is romanticism at its finest. It’s the album that unfortunately never got a tour (yet), but we visualized the best parts of the album with fur, frills, and pastels that embody the feeling of being smitten.
Folklore
cardigan (plus) | turtleneck (plus) | jeans (plus) | booties
We can’t stop thinking about the cardigan—and no, we aren’t talking about the song (though that wouldn’t be a lie either). We’re talking about the one from her beloved Cardigan music video. Perfectly boxy, cable knit, and oversized to a T, it’s the piece we want to live in in this fall.
Evermore
sweater (plus) | shacket (plus) | corduroys pants (plus) | clogs
Evermore‘s surprise drop was in chilly December, and the red plaid she’s donning on the album cover makes this era veer ever so slightly toward winter, but we aren’t mad about it. Emulate it to perfection in deep, rich tones and a shacket that you’ll never want to take off.
Midnights
polo (plus) | pants (plus) | sneakers
Yes, Midnights is bound to have some celestial style tied to it (especially when she goes on tour, wink wink), but if we’re taking cues from her Anti Hero music video, she’s saying to throw it back to the ’70s. To be honest, we’re expecting retro, Midnightcore vibes to be trending any minute now, so you might as well get ahead of it while you can.
