Celebrity Style
All Of Taylor Swift’s Style Eras, From Her Debut Album to Midnights
With each album, we get a new aesthetic.
Taylor Swift’s latest album is about to drop, meaning before you know it, you’ll be lost in the stories that unfold on Midnights. As Swifties know, when she drops new music, everything is intentional — from the song lyrics to the liner notes, down to the outfits she wears to promote it. Each album serves as a new era and no detail is random.
For instance, if you’re a fan, then you know her 2017 album Reputation was littered with references to her public feud with Kim Kardashian and then-husband Kanye West. With the release, her look noticeably shifted from America’s sweetheart to bad b*tch. Her makeup got darker, her outfits edgier, and nearly every ensemble included a snake motif or print. Swift wore the look like a badge of honor, as if to say ‘you can call me a snake, but I’ll stand tall in my truth.’
Meanwhile, since announcing Midnights at the VMAs, we’ve seen her take on a glitzier, more glamorous style with some vintage elements. She’s been stepping out in dazzling looks recently, including sparkling party dresses that evoke the feeling of staying up late and dancing under the stars.
Beyond that, her outfits on social media and previews of the vinyl covers deliver a distinctly retro feel that’s reminiscent of the 1970s.
On that note, ahead of the imminent release of Midnights (Oct. 21), take a look back at Taylor Swift’s different style eras and how they correspond with each of her albums.
Taylor Swift, 2006
Swift’s debut, eponymous album was synonymous with sundresses and cowboy boots. The look, along with her famous ringlet curls, was Swift’s signature in ‘06. She was just 17 years old and trying to find her place in the industry as an up-and-coming country singer. There was no shortage of twee floral prints and frills in her closet. For formal events and music videos, however, she would go full-on princess in cupcake-like prom dresses. It was practically another lifetime, kids.
Fearless, 2008
2008 is the year Taylor Swift really started to pop off, becoming a household name as a country-pop artist. When she dropped her second album, Fearless (which makes me beyond nostalgic), she donned an abundance of girly dresses embellished with sequins and fringe while on tour. Ultra-femme dresses, flouncy skirts, blazers, and flowy blouses were also staples for her. This era saw Swift slowly start to ditch her cowboy boots and move towards riding styles, as well as ballet flats, and heels.
Speak Now, 2010
Much like Folklore and Evermore, Swift’s third studio album had a romantic, somewhat mystical quality. With song titles like “Enchanted,” this equated to a wardrobe of fairytale dresses featuring tulle, sparkles, and sweetheart necklines. When she wasn’t wearing Free People-esque dresses, Swift could often be found in skinny jeans tucked into boots, frilly blouses, and lace-up oxfords.
Red, 2012
When she first released Red — Swift’s first foray into more pop-focused music — her style was polished and feminine with a retro, nautical twist. In 2012, she looked as though she should be sipping cocktails with Betty Draper from Mad Men. The pop star sported strings of pearls, timeless sunglasses, kitten heels, tea-length dresses, and (you guessed it) endless shades of red. This was also around the time she adopted her signature blunt bangs.
1989, 2014
In her song “Style,” Swift sings “I got that red lip, classic thing that you like,” and also references wearing a “tight little skirt.” This was very much her vibe during her 1989 period. This era highlighted Swift growing up and having fun on her own in New York (as opposed to Nashville during her country music stint) and looking amazing while doing so. Swift chopped her hair into a chic bob and wore a lot of crop tops, matching sets, booties, and slouchy beanies.
Reputation, 2017
Swift’s Reputation era followed a tumultuous year of drama at the hands of Kanye West. The situation escalated and Kim Kardashian subliminally referred to Swift as a snake on Twitter. This served to catalyze a darker tone for Swift, musically, with song names like "Look What You Made Me Do.”
Her fashion choices aligned with this and soon she was wearing a lot more black and proudly rocking snake motifs. Overall, her ‘fits were moody and grungy, with thigh-highs, combat boots, leather, and camo on heavy rotation.
Lover, 2019
Lover, which is thought to be an ode to her relationship with boyfriend Joe Alwyn, was something different entirely. It was all about vibrant hues, sparkling accents, and temporary hair dye (she sported blue ends on the album cover). She took to performing in eye-catching, rainbow fringe-embellished looks. There were a whole lot of sequins during this phase, too.
Folklore & Evermore, 2020
Released five months apart in 2020, Folklore and Evermore were written during the lockdown stage. Both albums have a similar woodsy, cottagecore aesthetic, defined by cozy knits, flannels, autumnal plaid coats, and romantic dresses in velvet and lace. Swift rocked cardigans, chunky turtlenecks, flower crowns, and frocks with ribbons, and wore her wavy hair in braids.
Midnights, 2022
As I mentioned, the singer-songwriter has been bringing all the glamour to coincide with her tenth album. At the VMAs, she made a surprise appearance, showing up in an Oscar de la Renta dress dripping in crystals.
At the afterparty, she changed into a midnight blue Moschino romper covered in shimmering stars with a faux fur white coat on top and glittery Alexander McQueen platforms. The starry, retro-inspired look felt like something you might have seen at Studio 54.
Moreover, the album’s artwork, her looks, and even the set design, make it evident that the Midnights mood is very ‘70s. TLDR; She’s in her disco ball era.
