Taylor Swift's Style Eras, Ranked From Worst To Best

Each Taylor Swift album cycle has been marked by a shift her in style sensibilities. She knows how to take branding to the next level ad that's why, from the spiral curls to vintage dresses, Swift has evolved her persona with each new release. Her personal style has become inextricable from her art. And while Swift has been caught wearing her fair share of outdated trends, she remains serious style goals. In part, that's because her fashion choices have been shaped by the artistry of her albums, rather than trend cycles. "I think that as much as you should be creative and experiment, there are certain things I know are fads, and so I try to steer clear of most of the obvious ones," she told ASOS Magazine in 2014 (via Glamour). "I play the tape of my life forward and don't wear the things that my kids or grandkids will make fun of me for wearing."

But not all of her eras have been created equal and some of them have been more stylish than others. Her earliest style periods lack the power of her later ones, while others — we're looking at you "reputation" — prioritize making an artistic statement over flattering style choices. Swift isn't a necessarily fashionista. Of course, she works with a stylist. But her music is built on relatability and her wardrobe choices usually work to reinforce that persona. Still, when this delicately featured beauty gets it right, she gets it really right.

While this really only became an era in hindsight, the period certainly had its own look: curly hair, bohemian sundresses, and cowboy boots. These years, from 2006 to roughly 2008, are associated with Taylor Swift's first self-titled album and have come to be affectionately known by fans as the debut era. Swift got her start as a country music ingenue and, during these years, she looked the part. Her minimal makeup emphasized her youth and wholesome image, as did the age-appropriate sundresses. Her ringlets suited the romantic themes of her music, and this era gave us some of her Taylor Swift's most iconic naturally curly hair moments. Finally, her cowboy boots are giving major country star. "I get so excited about these [award shows] because I love to dress up," she told Entertainment Weekly in 2007. "But I wear cowboy boots so that when I walk down the stairs I won't fall."

During this period, Swift was firmly branded as a country star and had yet to refine a clear personal fashion style of her own. Instead, the pop star got a little lost amidst the contemporary styles of the time, including black eyeliner, aqua blues, and handkerchief hems. She looks pretty but never quite makes a powerful artistic statement through her style. Her styling is consistently youthful and charming, but it lacks the polish and impact of her later aesthetic eras.

After several years, during which she was largely absent from the spotlight, Taylor Swift returned to drop her sixth studio album, "reputation." The album, and its greater aesthetic era that lasted from 2017 through 2018, presented a Swift who was harder and edgier after surviving a public cancellation. Though it's arguable the singer was, at the time, a celebrity who was unfairly villainized for her mental health, when she finally did make a comeback, she made sure she wasn't letting anyone else define her. She abandoned the innocence and prettiness of her early eras for a new look that was edgier and bolder. Her styling choices featured darker colors like red and black, oversized hoodies, plenty of thigh-high boots, and a recurring snake motif.

In general, Swift made fewer public appearances during this period — in part due to her hyper-private relationship with then-paramour Joe Alwyn, but also because she was still grappling with the fallout from her 2016 feud with Kanye West and the ensuing cancellation. As a result, she offered up fewer street style and red-carpet looks to reinforce the "reputation" era — though, in a sense, her absence was an aesthetic choice to suit the album.

That said, when she did step out, her personal style choices included sexy silhouettes and dark colors that supported the album's branding, like the glittering red and black dress she wore to the New York City premiere of "The Favourite" in 2018. Still, this era feels a bit costume-y, in part because the villain persona Swift tried to put on doesn't feel genuine. The harsher aesthetic contradicts Swift's delicate beauty and natural coloring so in the end, she just looks like a kid playing dress up.

The Fearless era, the second of Taylor Swift's album-inspired aesthetic eras, lasted from roughly 2008 to 2010 and featured sparkling dresses, flapper silhouettes, and princess curls. Swift was still a country star at this time, quickly becoming a mainstream sensation thanks to hits like "You Belong With Me." She still sometimes wore cowboy boots but she was quickly shedding the casual styling of her "Taylor Swift" era for glittering ensembles that suited a rising star. But despite her fame, Swift's style still emphasized relatability. "I love sparkly headbands, so I go to the craft store and buy ribbon to make my own," she told Seventeen in a 2010 interview about her style secrets. "You don't have to spend a lot of money. I go in there and just have so much fun in the ribbon section."

Her looks during this period are more fairy tale than fashionista, which suits the wild romance of songs like "Love Story." Gold, yellow, and white all featured prominently in the "Fearless" era color palette — optimistic colors that suited Swift's youth and exuberance. Notably, Swift began to shift from away the style of an aspiring teen musician and embrace the glamor of superstardom. During this period, she also began working with stylist Joseph Cassell. Still, this era is ranked relatively low because, while it does make a more coherent statement about Swift and her music, it doesn't fully differentiate itself from the aesthetics of her debut era.

From 2019 to 2020, Taylor Swift was all about a romantic, pastel-forward aesthetic that reflected the branding of her 2019 album, "Lover." The bright, colorful vibe was a big U-turn from the edgy, black looks that characterized the preceding "reputation" era. The pop star, seemingly over the moon about her relationship with Joe Alwyn, appeared to have rebounded from her cancellation and arrived in a calm and stable relationship. She marked it with swoony pastels, hearts, sequins, and whimsical, maximalist styles that conveyed a newfound softness. Swift even teamed up with Stella McCartney for a limited run of "Lover"-inspired pastel tie-dye sweatshirts.

This era certainly gets points for its joyfulness. In some ways, the romantic looks she wore on the red carpet, like the Greek-inspired J. Mendel gown she wore for the TIME 100 Gala, almost call back to the heady optimism of "Fearless." The feminine colors and dreamy styling are suited to Swift's ethereal beauty. Unfortunately, not all of the looks were as flattering, sometimes veering a little too hard into neon. Still, on the whole, this was a fun and memorable style period for Swift.

The "Evermore" era, following the release of the 2020 album, refined the cottage-core aesthetic that Taylor Swift debuted with the release of "folklore." The two pandemic albums are considered to be sister albums, and "evermore" didn't necessarily get its own style era — especially because, during this period of lockdown, Swift made fewer public appearances. Still, there are a few key details unique to "evermore," which represents a sort of stylistic bridge between the cozy whimsy of "folklore" and the 1970s chic of "Midnights." This style period is marked by flowing dresses, plaid coats, and earth tones.

At the 2021 Grammys, Swift performed wearing an Etro dress that epitomizes the bohemian-inspired vibe of "evermore." The dress features a metallic print, full sleeves, lace trim, and a high slit. It's pure Joni Mitchell. Where the dresses of the "folklore" era feel innocent, "evermore" is a more sophisticated spin on the flowing, earthy styles that characterized this album cycle. It's a more mature, elegant version of cottage-core. These styles are undeniably beautiful, we just wish they felt a bit more distinct from the "folklore" era — it might make them more memorable.

Taylor Swift shed much of her country star styling when she released her 2010 album "Speak Now." This new style period was characterized by romantic fashion choices. Her gowns during this era tended toward soft, feminine color palettes with dreamy detailing, like the black lace accents on the pink gown Swift wore for 2011 Met Gala event. Her style was less Nashville and more theatrical as a stronger pop strain emerged in her songwriting, and Swift began to introduce more vintage pieces into her heretofore romantic country star wardrobe. This era also marked the introduction of Swift's signature red lip, a style statement that has marked nearly every style phase since — that's thanks to celebrity makeup artist Gucci Westman who prepped the singer for a photoshoot in 2009. "I remember I really wanted to do a red lip on her because I hadn't seen her in a red lip before," revealed Westman during a 2024 episode of "TODAY with Jenna & Friends." "Look at her now."

And while the red lip is iconic, and the feminine styles are flattering on the fine-featured star, this era just feels confused. It presages the vintage dresses of the "Red" era, while calling back to the high romance of "Fearless." Like the "Speak Now" album, Swift appears clearly caught between her country roots and her pop star future, which makes her style somewhat forgettable.

The 2012 album "Red" marked the beginning of Taylor Swift's hipster era. Though still ostensibly a country album, Swift was moving more definitively into the pop market, and her style, with its emphasis on high-waisted shorts, preppy dresses, and vintage silhouettes, reflected that transition. Swift embraced plenty of hipster details — like the thick framed glasses she wore for the "We Are Never Ever Getting Back Together" music video — and favored brands like ModCloth and Urban Outfitters. It seems she meant it when she sang, "It feels like one of those nights to dress up like hipsters" on the opening of "22."During this era, Swift introduced blunt bangs as part of her hairstyle after having them cut on the set of a 2011 Vogue cover shoot. Though her hair has changed with each era, the bangs have remained, in some form, ever since.

If the "Speak Now" era had felt stylistically confused, "Red" ushered in a fashionable Swift with a clear sense of self. Her style during this period seems to find an organic balance between prevailing trends and Swift's own natural instincts toward classic, feminine styles. Her looks also work well to support her now undeniable pop sound, which was making her a serious crossover threat. All around, this era was a fashion hit.

"The Tortured Poets Department" inverts the color palette of the "reputation" era, swapping black with white accents for white with black accents. Though this style era has blended, to some extent, with Swift's high-glam "Midnights" era, it is distinguished by a Victorian influence. It's clear that these days, Swift is a master of creating clearly defined aesthetics to differentiate her album eras, and this album was her full blown dark academia phase. It's Gothic luxury, with sumptuous textures, cinched corsets, and lots of Vivienne Westwood. It's best epitomized by the dress Swift wore when she announced the album at the 2024 Grammy Awards: the look was a detailed white gown offset with elbow-length black gloves and delicate jewelry. The moody ensemble introduced the album's new look and Swift's new style.

This new style era is peak Swift melodrama and perfectly embodies the unhinged heartbreak of the album it's tied to. Plus, we love seeing the sexy edge that Swift has introduced with these revealing leg slits. This is pop star dressing at the best: gorgeous and narratively satisfying.

The cozy cottage-core of Taylor Swift's 2020 pandemic album, "folklore," was a dramatic transition for the singer who had just embraced the saccharine, hyper-feminine styling of "Lover." Instead, the "folklore" era, with its emphasis on natural colors and prairie dresses, reflected a singer who was getting more intimate and personal in her music. Gone are the sleek and shiny blowouts as Swift flaunts her natural wavy hair texture. It was a totally new side of Swift, who seemed to be trading her pop star glamor for a more organic aesthetic. That was, in part, out of necessity. Swift styled herself for the "folklore" cover shoot due to COVID concerns. "You can't have hair and makeup. You can't have wardrobe. You just have to do it yourself," Swift revealed during an Eras tour stop, captured in a fan's TikTok video. "I ordered all these night gowns online and brought them and did my own hair and makeup and just was like, 'I guess I'll braid it, I don't know.'"

The dramatic pivot from Swift makes this one of her best style eras to date. The dreamy styles suit the singer beautifully, and the pared down looks deeply reflect the more stripped back, acoustic sounds of the "folklore" album.

With the "1989" era, Taylor Swift transitioned from country singer to full-blown pop star and her wardrobe got an update to match. Her style got sleeker and more modern as she debuted a new platinum blonde bob, and reached for coordinating sets, sky high heels, and bold colors. This was the period when Swift began to fully embrace the world of high fashion — after all, who could forget her squad of fashion model friends? During this period, Swift often favored coordinated, or even matching, outfits with pals like Karlie Kloss. That's in part because this era was all about the girls as Swift distanced herself from her previous reputation as a "boy crazy" girl and began to rebrand as an independent, powerful woman. As a result, the looks are more sophisticated and elegant than anything she had donned before.

It's hard not to love this new, more fashion forward Swift at the height of her power. The glamor is pure pop star. This era ranks high because it was so memorable, and because it is perhaps her most defining moment, sonically and sartorially.

"Midnights" might be Taylor Swift's sexiest era. Characterized by luxe textures and celestially details, it's pure '70s glam. The sequins are giving Studio 54. The revealing looks suggest new agency and self-possession from a star who has matured and knows herself well. Where her looks once telegraphed innocence and youthfulness, they now suggest confidence and control. Swift has never looked more like the mega star that she is then when she's dripping in diamonds, as she was in an Oscar de la Renta mini dress at the 2022 Video Music Awards. It's the dress that literally kicked off the "Midnights" style era since the singer took the chance to announce her forthcoming album.

This style era gave us a sexier, bolder version of Swift, unafraid to look like a total babe while still making appropriate reference to the lyrics and motifs of the "Midnights" album ("Bejeweled," anyone?). Perhaps that's why this style era has had such staying power, blending into the Victorian-infused looks of "The Tortured Poets" era looks. After all, who could begrudge her the sparkle? As Swift herself sings, "A diamond's gotta shine..."

A variety of factors went into determining how we ranked Taylor Swift's style eras. Thought was given to the aesthetics that were most flattering on the pop star; we judged how the most notable looks from each era that suited her coloring and delicate features. The greatest consideration was given to how the style period differentiated itself from her other creative eras, and how much it reinforced the narrative and branding of the era's associated album. Style eras that appeared to have a less coherent feel, or ones that simply did not feel sufficiently different from other stylistic periods were ranked lower than style eras that clearly marked a new chapter in Swift's life and creative work.