Taylor Swift Street Style: 1989 Era

The urge to cut my hair into a bob is overwhelming.

On the eve of 1989 (Taylor’s Version) being dropped, I thought it was appropriate to share a project I have been working on since 2020. During quarantine, I made it a game of trying to find items of clothing Taylor Swift has worn (in my size) on secondhand online stores (namely Poshmark, thredUP and Mercari). Finding an exact item online scratches an itch in my brain. I’m like a pirate hunting for treasure. I’ve done this series for almost all of her other eras (click here to check out Fearless, Speak Now, RED, reputation and Lover) so of course I had to do an entire post dedicated to 1989. I’ve always admired Taylor’s ability to shift into different eras with her clothes and hairstyle. I think her 1989 street style is the most recognizable of her eras and had the most intention and planning behind it (who leaves the gym in 6 inch heels?!) So allow me to transport you back to 2014 & 2015 as we dive into what made her 1989 era so unique and where I found these outfit pieces, incase you feel like recreate some of these looks too.

As I continue to make these posts, I really start to understand how quickly trends and styles evolve over the years. I either thrifted or already owned everything you see in these posts. However, I did try to include some affiliate links to items that are currently available online that look similar to what I/Taylor is wearing in these photos.

I also wanted to add that I am selling a bunch of the items you see in this post on my Poshmark!

I want to add a small “disclaimer” (if you can even call it that) that I am a size US 12-14. I have a pretty strong guess that Taylor was not that size when she wore all of these outfits. This is not meant to be a “Taylor Swift’s style shown on midsize girl” case study. I’m a firm believer you can wear whatever you want, whenever you want. But I wanted to add this because I know I look nothing like Taylor Swift and I think it’s pretty bold of myself to put a side by side comparison of the two of us on the internet. But I loved putting these outfits together and taking a stroll down memory lane in order to put everything together. And also, when I say “it’s the same dress” I don’t mean the exact same dress straight from Taylor’s closet. I mean the same brand and design, just in my size.

Outfit #1

I have been on the hunt for this dress for so long! This outfit is very special to me because Taylor Swift wore this outfit in NYC the day she performed in DC for the 1989 World Tour show I attended. I remember seeing these pictures on Twitter and thinking “why is she in New York? I’m literally at the stadium in DC right now.” I also remember everyone freaking out that this outfit was very “Speak Now” era because of the headband, vintage style heels and the mystical essence of the dress. I love boho Taylor! So after searching high and low for this dress on Poshmark, I finally found it in the color I wanted. I am currently selling it on Poshmark for anyone who is interested. If you’ve seen my other recreation posts, you may recognize the sequin bow headband I’m wearing from this post.

Outfit #2

I was so happy to find this skirt on thredUP! I randomly stumbled upon it while browsing and immediately added it to my cart. And of course, I am reselling it on my Poshmark. In my opinion, this is a very recognizable 1989 era look. We all know this girl loved flare skirts and crop tops back in the day. This is so quintessentially girly and preppy, which is only slightly out of my wheelhouse. But we love a “good girl faith and a tight little skirt” moment.

Outfit #3

I am so glad I kept this skirt from 2016. This is an outfit straight from my own closet, even if I haven’t worn it since college. This skirt was definitely very trendy back then (every hot girl wore this skirt for Thanksgiving, at least once, right?) so I feel this is an appropriate point in this point to mention that while Taylor’s style tends to be very “trendsetter”, she and her stylist definitely take cues from what is popular at the time. But you can also bet that Taylor can always throw in those grandma-looking oxford shoes to really embrace her own personal style.

Outfit #4

I love how much Taylor loves Free People. Since the Fearless era, Taylor has worn Free People countless times. I think this dress is both boho and feminine, but also such an effortless look. Boho Taylor is one of my favorite Taylors. This dress is also very easy to find on a secondhand shop (in multiple colors) but I do want to add I am also selling mine.

Outfit #5

One of her best looks from the 1989 era! She wore this outfit walking through Central Park with a writer from Rolling Stone for her 2014 Cover Story. The pop of pink in the shows is my favorite part, and the Starbucks cup is a paid actor. I have been holding onto this outfit since 2020. I was so happy to find it in my size on Poshmark, and I have just been waiting to do a full post like the one you’re currently reading. This outfit was especially hard to find dupes and similar skirt sets (but I am selling mine on Poshmark!)

Outfit #6

Taylor wore this outfit after seeing the 1975 in LA. You may remember that Matt Healy wore a 1989 t-shirt during one of his shows back then. I have no idea what went on between them, but I obviously I had to replace the 1975 shirt in the OG photo with my 1989 tee. This outfit is giving very much 2014 Tumblr vibes (the girls who get it, get it) and I wouldn’t be surprised if this exact look made a comeback in 2024.

Outfit #7

Alexa, play “Welcome to New York”. Taylor really does love repping NYC, and this Brandy Melville sweater is a great cross between “new to town” to “preppy Hampstons gal”. Very cute and very easy to recreate. I think I would like this outfit more if I was a New York girlie. If you consider yourself to be, you can buy this sweater on Poshmark. And of course, the oxford heels make another appearance.

Bonus Outfit

If you are aware of the history and backstory of this sweater, you may be eligible for compensation. Taylor has worn this Genuis sweater during multiple eras, but she infamously lent it to Karlie Kloss during their Big Sur trip. I decided to use screenshots of this IG video of Taylor wearing the sweater while blowdrying her cat to showcase this sweater, because to me, this sweater is very symbolic of this era. It’s a blurry video, but I wanted to show off that I own this one. I can’t decide if I want to part with it or not…

Which is your favorite outfit? Let me know in the comments.

Thanks for reading! xx