Whether you’re looking to get that red-lip classic thing and/or a tight little skirt, here are some of Taylor Swift’s most iconic outfits over the years — plus where to steal each look. You might wanna get a blank space to write stuff down, so you’ll never go out of style.

With the rerelease of her Grammy Award-winning album Fearless, Taylor Swift’s version gifted us with six brand new tracks straight from her vault. That throwback got us thinking — perhaps we, too, should journey back through the years and check how Taylor evolved, not just in her sound, but in her style choices as well.

Protip: Her tunes were pretty much the soundtrack to many of my best high school years, and I’m sure they were yours too! Get the most fun out of this read by blasting your favourite Taylor Swift track as you scroll through the article.

Nostalgia… Ready for it?

Self-titled Album (2006)

It wasn’t her rendition of The Star-Spangled Banner at a Philadelphia 76ers basketball game that got her the contract with Big Machine Records. Rather, it was a performance at The Bluebird Cafe in Nashville that gave her the big break she needed. Rock that same girl-next-door look with an embroidered frock and curly waves — brownie points for cute guitar straps.

Credits: Billboard

Get the look: Love Bonito’s Blyana Jacquard Camisole Dress from S$57.

Fearless (2008)

It was with Fearless that Taylor first tried her hand at producing records — and it paid off, earning this album the coveted spot of the best-selling album in 2009. Trade-in those short skirts and t-shirts for a luxe ruched gown that will definitely catch the attention of your crush (and everyone around you) whether you’re on the football field or the bleachers. Give a nod to the queen of pop with a silver embroidered headband for extra oomphf.

Credits: Hollywood Reporter

Get the look: Farfetch’s Alexander McQueen Ruched Detailing Strapless Gown from US$3700 (~S$4900).

Speak Now (2010)

Taylor’s third album was the sum of her country roots, heartfelt songwriting and glam pop-rock production. Unlike the past two albums, Taylor wrote the entire album on her own. And what says a renewed sense of individuality better than a glittery 1920s-inspired flapper mini dress? 

Credits: Nashville Lifestyles

Get the look: Lulus’ Get in the Groove Champagne Sequin Fringe Bodycon Dress from US$86 (~S$115). 

Red (2012)

In an interview, Taylor mentioned that her fourth album was born out of an influx of emotions that had expanded since her earlier days of dole-eyed fairytale-d innocence. They now took on a fiery red hue, “spanning from intense love, intense frustration, jealousy, and confusion”. The next time your emotions turn red, channel all that inner angst into your #ootd — don’t forget to tie the look in with Taylor’s signature bright red lipstick. 

Credits: Billboard

Get this look: ASOS’s Iridescent Sparkle Long Sleeve Top from £55 (~S$102), Zalora’s High Waist Shorts from S$25.

1989 (2014)

If Red was the angsty teenager, 1989 would be the mellowed-out cool young adult of Taylor’s discography. She no longer feels the need to express all her emotions in song like in Red, but rather, she’s now able to feel it but take on the observant role of a nonchalant bystander. Her fifth album is her rebellious response to critic’s feeble attempts to shame her for dating too many men. Switch things up with a shorter playful bob and shake off all those haters in this fun two-piece retro plaid set. 

Credits: Rollingstone

Get the look: Amazon’s Romwe 2-Piece Crop Tank Top with Skirt Set from US$10 (~S$13).

Reputation (2017)

Taylor’s sixth addition to her grammy-studded discography kept fans and critics who thought they knew her guessing. While it comes across as a little petty, like a scorned lover scratching up her ex’s car, Reputation painted Taylor in a whole new aggressive light and furthered secured her spot as the queen of modern pop. Get Taylor’s bad-and-boujee look with this beaded bodysuit and crimson lipstick, attitude sold separately.

Credits: thelineofbestfit

Get the look: AKIRA’s Never Going Home Beaded Long Sleeve Bodysuit from US$49 (~S$65).

Lover (2019)

The New York Times described Taylor’s seventh album best as “a recalibration, playing to her old strengths while hinting at new paths forward”. If the old Taylor had died in Reputation, Lover was her resurrection — but better and stronger. Her fun anthems now had an edge to them, these love songs were now coated in the wisdom that she had gleaned over the years. Nothing says “make love not war” like this tie-dyed fringe jacket and shorts. 

Credits: NME

Get the look: ASOS’s Blank Nyc Tie Dye Fringe Denim Jacket from £109 (~S$200), Shein’s Knot Waist Tie Dye Dolphin Shorts from S$9. 

Folklore (2020)

Moody, cinematic and indie — Folklore was an enchanting melancholic shift that pairs her heartfelt songwriting with strings and guitar loops. Round up some friends, rent a caravan and head into the forest for Folklore vibes. Complete the look with an oversized sweater but prepare to get those white sneakers muddy. 

Credits: Entertainment Weekly

Get the look: ASOS’s New Look Rugby Collar T-shirt With Heart Embroidery In Black Stripe from £12 (~S$22), Uniqlo’s Ezy Flannel Ankle-length Pants In Check from US$40 (~$53).

Evermore (2020)

Shortly after Folklore, Evermore surprised fans with its release. Pitchfork described Evermore as a companion album to Folklore, built from the same general sounds and personnel — with its goal not being the recapturing of folklore’s cabin getaway-type glow but rather, “to extend her stay for another season”. 

Credits: New York Post

Get the look: ASOS’s Liquorish Boxy Straight Coat from £52 (~S$96). 

Fearless (Taylor’s Version) (2021)

The first of six remakes, Fearless (Taylor’s Version) is the singer-songwriter’s way of reclaiming legal ownership of her music. There are clear differences, whether that be in its inflexions, tone and depth, as well as clarity of instrumentation — but more importantly, this version of Fearless is a revisitation of old memories by a more polished and stronger Taylor. 

Credits: Rolling Stone

Get the look: Beachsidebunny’s Lucent Bohemian Wrap Dress from S$100.

Even If It’s Just In Your Wildest Dreams

You can now be in Taylor Swift’s Squad — or at least look the part anyways. If you noticed, we’ve kept the ASOS price listings in GBP to help you save some $$ (as well as any potential teardrops on your guitar). Just remember to checkout with your YouTrip card  to score more with our sweet Wholesale Exchange Rate. Don’t forget to check ASOS Promo Code Singapore for promo codes too!

If you still haven’t gotten your free YouTrip card yet, use promo code <BLOG5> to sign up and receive a free S$5 in your account. 

For more great tips and guides like this, join our Telegram Community (@YouTripSquad) and subscribe to our free weekly newsletter here or down below!

Related Articles

BTS’ Jungkook: 4 Products That The K-Pop Star Accidentally Helped To Sell Out

Netflix’s ‘Bling Empire’: Here’s How You Can Recreate These Iconic Looks On A Budget

Reverb: Beginner’s Guide to Online Shopping for Acoustic, Electric & Used Guitars

^{*All currency conversion rates are accurate to the nearest dollar on 20 April 2021 SGT 16:00. Top banner image from Bandwagon Asia.}