All of Taylor Swift's Best Fashion Eras, From "Red" to "Midnights"

Published on 6/14/2023 at 7:10 PM

Taylor Swift has had many a style evolution — and fans have breathlessly followed each one. When the "Bejeweled" singer initially stepped out in boho dresses and cowboy boots, Swifties immediately began doing the same. And when she entered her preppy early-aughts-inspired era in knee socks and miniskirts, her supporters followed suit. Over the course of her nearly 20-year career, Swift's fashion has run the gamut from princess moments to sultry evening dresses, embellished bodysuits to naked dresses. As far as inspiration, the 33-year-old star looks to a variety of muses, including preppy schoolgirls and early-aughts teens.

When Swift finds her uniform of sorts, she sticks with it. And the acclaimed songwriter is famous for marrying those fashion moments to eras in her career, which also coincide with her albums. She playfully nodded to this phenomenon with the Eras Tour, where fans have been re-creating past aesthetics with their concert outfits. Drawing from the most iconic Swift outfits, attendees may embrace the snake theme as a nod to her "Reputation" era or gold sequins to reference her current "Midnights" era.

It also helps that the superstar loves to wear accessible fashion brands. Swift's street style looks often include a piece or two from retailers her fans shop from often, including Reformation and Polo Ralph Lauren. Swift's looks for star-studded events, like the VMAs or the Met Gala, are decidedly more high end. Take her Oscar de la Renta dress at the 2022 MTV VMAs or her Balmain dress at the 2018 AMAs; both are runway ready and glamorous, like most of Swift's red carpet outfits.

So with her current world tour in full swing, it's time to take a walk down memory lane with Swift's fashion moments over the years — from the red carpet to the streets of New York City and everything in between.

Taylor Swift at the Grammy Awards, February 2023

At the 2023 Grammy Awards, Taylor Swift hit the red carpet in a navy crop top and skirt designed by Roberto Cavalli and oversize statement earrings and rings from Lorraine Schwartz.

Taylor Swift at the MTV VMAs, August 2022

Taylor Swift rocked a take on the naked dress at the 2022 MTV VMAs in an Oscar de la Renta chain-link minidress that was totally sheer, save for the allover embellishment. Her jewelry was by Lorraine Schwartz, and her heels were from Christian Louboutin.

Taylor Swift in NYC, June 2022

Taylor Swift borrowed from the boys with a Max Mara suiting look in NYC in June 2022, choosing to wear a waistcoat with nothing underneath. She wore it with Vrai earrings and rings, along with Prada pumps.

Taylor Swift at the Grammy Awards, March 2021

For the 2021 Grammy Awards, Swift went for a spring theme, slipping into a gorgeous embroidered floral dress from Oscar de la Renta. She paired the look with pink ankle-tie heels from Christian Louboutin and Cathy Waterman jewelry.

Taylor Swift at the American Music Awards, October 2018

Taylor Swift channeled a disco ball at the 2018 AMAs, dressed head to toe in Balmain with a metallic minidress and thigh-high boots, styled with Lorraine Schwartz jewelry.

Taylor Swift in NYC, July 2018

Taylor Swift's summertime take on the Canadian tuxedo consisted of a Madewell denim crop top and black denim Ksubi shorts. She kept it casual with a pair of white sneakers from Golden Goose, Jimmy Choo sunglasses, and a Christian Louboutin backpack slung over one shoulder.

Taylor Swift at the Met Gala, May 2016

Going for a futuristic look for the Met Gala that she hosted in 2016, Swift slipped into a cutout metallic minidress from Louis Vuitton with black heels that crisscrossed their way all the way to her knees. Her jewelry was designed by Eva Fehren, Massia Cielo, and Borgioni.

Taylor Swift at the Grammy Awards, February 2016

Taylor Swift went for full-blown color at the 2016 Grammy Awards, dressed in a Versace crop top and high-waisted ball skirt with an up-to-there slit that showed off the built-in briefs underneath. On one hand were two rings from Ofira, while the rest of her jewelry was designed by Lorraine Schwartz.

Taylor Swift in NYC, September 2014

Taking her white kitten for a stroll in NYC, Swift went for a schoolgirl-inspired look, slipping into a plaid miniskirt from RD Style, a white top from Free People, crocheted knee socks from Tabbisocks, and pumps from & Other Stories.

Taylor Swift in NYC, August 2014

Taylor Swift loves a matching set, and she rocked a sheer striped floral miniskirt and cropped tee from H&M with Elie Saab heels in New York City in August 2014.

Taylor Swift in NYC, July 2014

In the mid-2010s, Taylor Swift loved a Reformation moment, and this look was no exception. In NYC in July 2014, she wore a shorts romper from the brand with Gucci pumps and a neutral handbag.

Taylor Swift in NYC, July 2014

Taylor Swift was ladylike with a twist while in New York City in July 2017, wearing a polka-dot slit pencil skirt and matching crop top, both from Reformation. On her feet were Pikolinos heels, and she carried a bag from Kate Spade.

Taylor Swift at the Met Gala, May 2014

A longtime Met Gala attendee, Taylor Swift leaned into the couture angle for her Charles James celebratory evening in 2014, wearing a custom Oscar de la Renta gown, Lorraine Schwartz jewelry, and Christian Louboutin heels.

Taylor Swift at the CMT Music Awards, April 2007

In a posh princess moment, Taylor Swift hit the red carpet at the 2007 CMT Music Awards in a BCBG Max Azria sequined tulle dress.

Taylor Swift at the Academy of Country Music Awards, May 2006

At the 2006 Academy of Country Music Awards, Swift leaned into her bohemian Southern roots with a printed handkerchief halter dress from BCBG Max Azria, styled with cowboy boots.