I Dressed Like Different Taylor Swift Eras for a Week & It Made Me Feel Fearless

Like many others, I was extremely excited for Taylor Swift to rerelease Fearless and to relive all that sweet, sweet 2009 nostalgia. To prepare for the new album, my friends and I have listened to hours of Taylor’s old music, debated cryptic messages in her social media posts, and even made a bracket ranking all of her songs — unsurprisingly, “All Too Well” was the winner. 

All this time digging into different Taylor Swift eras made me miss the sparkly dresses she wore in the Fearless era, the preppy pin-up look of Red, and the oversized grunge pieces of Reputation. I miss seeing her walk a red carpet or post a picture to Instagram as all of social media went crazy admiring a new look that she was trying out. In all of her eras, Taylor was a style icon — she still is! So I got inspired to recreate some of her most iconic styles with pieces from my closet. 

This was my time to pop on a red lip, tear through my closet and pick up a sundress or two at my local thrift shop, and try out a new Taylor fashion era for a week. Here are how the looks came out.  

  1. 1. Day one: Fearless era

    Taylor swift inspired outfit

    While my dream would be to buy one of those sparkly fringe mini dresses Taylor wore on tour, unfortunately, anything she would have worn was too expensive and impractical for a day on campus. Instead, I focused on her daytime looks which were mostly sleeveless sundresses.  

    This outfit was extremely easy to put together. I found this cute sundress at a thrift store for only $8 — a total steal — and paired it with brown heeled booties that I’ve owned for years. I hadn’t worn these shoes since high school, but when I went outside in this outfit I got two compliments on them, so I think they will reenter my rotation. If you want to go for some more Taylor authenticity, match your dress with a pair of cowboy boots. 

    Unlike many of her other eras, Taylor didn’t wear a lot of makeup back then, so I focused on my skin for an almost makeup-free look. All I needed was a sweep of a darker blue or purple-toned eyeshadow, black eyeliner, and a peachy pink lip to brighten my face. Overall, this was a look that I will definitely try again for days when I’ll be walking outside and want to keep it casual.

  2. 2. Day two: Speak Now era

    taylor swift inspired outfit

    I originally planned a second sundress look for the second day, but the weather became extremely cold, so that was no longer an option. Instead, I looked online for other looks that scream 2010 Taylor Swift that I could make out of my wardrobe — all I want is to recreate the Speak Now album cover, but alas. Then I came across a few of her flannel and beanie outfits and couldn’t help but fall back in love with them — just look how cozy they look! Overall, this was a really easy look to recreate: I just threw on a flannel with a coordinating slouchy hat and black leggings. I went through a huge flannel phase a few years ago, so this allowed me to raid my old clothes and also made me question why I stopped wearing them. Makeup really was mostly centered around Taylor’s iconic matte red lip. The rest of the makeup was relatively simple: just a tint of blush and black eyeliner.

    I loved this outfit because it was an easy look to spend the entire day in as I went to a coffee shop to study. Flannels are perfect fall and springtime pieces because you’ll look great while not having to worry about fixing your outfit the entire day. To elevate it a bit more, I would pair this look with a monochrome scarf (perhaps one that reminds you of innocence and smells like me). 

  3. 3. Day three: Red era

    Taylor swift inspired look

    This was easily my favorite look for the week because it felt extremely sleek and really pushed me out of my comfort zone. I really love a black, white and red color scheme, so this was a really nice way to experiment with these colors. I love the trendy mesh back to this button-down, and these black slacks with a pair of saddle shoes (I bought these on Amazon two years ago and wear them all the time!). Once again, I did a red lip — lip liner is key in creating a Taylor-esque defined red lip — and went a bit heavier with the eyeliner for this look for a more pin-up style. 

     Unless it’s cold, I never wear hats — this one I stole from my sister — so I felt a bit uncomfortable at first. However, numerous friends and classmates DM’d me on Zoom to tell me how much they loved my outfit of the day. This was the one look that I didn’t think I would want to repeat, but it gave me a new boost of confidence and I think I might wear it out or to my internship this summer. 

  4. 4. Day four: 1989 era

    taylor swift inspired outfit

    Not going to lie, when I was picking Taylor Swift eras I wanted to recreate, 1989 was the one that I could distinctly remember the least about in terms of Taylor’s clothing. However, after listening to the album again — “Clean” still slaps — and looking back at her outfits for this era, I got excited. I loved Taylor’s big sunglasses, red lips, and fun mock necks. 1989 era clothing was the one closest to what I wear usually, but it still gave me some inspiration to break away from the black turtlenecks that I wear daily. For this, I chose a pale pink mock neck and a patterned denim skirt because so much of this era was based around using classic pieces with a twist. This outfit could not have been completed without a pair of oversized sunnies and a classic red lip.

  5. 5. Day five: Reputation era

    taylor swift inspired outfit

    No iconic Taylor Swift eras challenge would be complete without a tribute to Reputation, the period when she totally reinvented herself. I based this look off the album cover, and it isn’t something that I would usually wear. I didn’t really love the off-the-shoulder sweater nor the choker — another piece stolen from my sister. I wore the oversized sweater as a dress like Taylor did throughout this era, and might do something like that again, but my warning is that you really have to check how oversized what you’re wearing is because what may be long enough when you’re walking around may be way too short when you lift your arms. Overall, this was fun to put on an edgier look, but going forward I think I’ll just listen to Reputation instead of mirroring the look again.  

  6. 6. Day six: Folklore and Evermore era

    taylor swift inspired outfit

    For my final day of the challenge, I was inspired by the Folklore cover art, but chose similar pieces in my closet that I wouldn’t have normally paired together. I haven’t worn this oversized navy sweater in years, and I layered it over a long floral dress. I had never thought to pair them and both had been under-appreciated in my closet since I bought them. I was a bit nervous about pairing the black floral with the navy, but I think they were a cute, casual look that I will definitely be repeating again. 

Final thoughts

This week, I was able to dress like one of my style icons and wear pieces from my closet in a way I never would have. Next time you’re considering trying out a new style, choose your favorite Taylor Swift era and go for it! I realized that just because a few of these looks were worn 10 years ago, that didn’t mean I couldn’t make a few adjustments and rock them in 2021. 

Too often, I’m caught up with trying a new trend and buying more new clothes that I forget the dozens of outfits I already own. This really inspired me to go back into my closet, toss out what I know I wouldn’t wear again, but also to find some hidden gems that just scream Taylor Swift. If I’m ever feeling like I’m bored of my closet, all I need to do is look up Taylor Swift fashion and I’ll find hundreds of different looks and hopefully, that’ll inspire me to look back into my closet and try a new pairing on and perhaps even play Fearless (Taylor’s Version) for the hundredth time.