From her street style ensembles to her awards show standouts, here’s a look back at Taylor Swift’s best fashion moments over the years

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She started as a teen country singer with hits like “Tim McGraw” and “Teardrops On My Guitar,” but Taylor Swift has grown into one of music’s most prominent powerhouses. From seamlessly crossing over to the pop charts to living in New York City, fans have seen the star through many eras — and there are surely many more to come.

Over the years, Swift’s style has inevitably evolved along the way. While the singer gravitated towards romantic ball gowns and feminine silhouettes for her early red carpet moments, she’s stepped out of the box more recently with tailored suits and menswear-inspired looks. And just like with her music, Swift is bound to continue to surprise us with her style, whether she’s attending an awards show or strolling around Tribeca.

Keep reading for a look back at some of Taylor Swift’s best fashion moments.

Taylor Swift at the CMAs in 2006

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Shortly after releasing her very first single, “Tim McGraw,” Swift made her CMAs debut in a black, floor-length Elvira gown with black opera gloves. Her signature curls were on full display as well as a dramatic, smoky makeup look.

Taylor Swift at the CMAs in 2007

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Swift seemingly channeled Belle’s iconic yellow dress from Beauty and the Beast with her 2007 CMAs look. The brilliant gold gown featured a beaded bodice and satin skirt, and the star’s blonde curls were pulled back and swept over one shoulder. Rather than go for matching jewelry, Swift accessorized with long silver earrings.

Taylor Swift at the 50th Annual Grammy Awards in 2008

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For her very first Grammys, Swift embodied her newfound role as music’s girl next door in this strapless lavender dress with beaded detailing on the skirt. She didn’t take home any awards that night (she was nominated for Best New Artist, which Adele won), but the appearance was certainly a memorable start to her journey as a style icon.

Taylor Swift at the CMAs in 2008

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She was still firmly in her country music era, but Swift looked like a pop princess in this sequin gown by Kaufman Franco at the 2008 CMAs. The sheer black straps and plunging neckline gave the look a sophisticated feel.

Taylor Swift at the MTV VMAs in 2009

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Swift went for all-out glamour with her one-shoulder Kaufman Franco gown at the 2009 VMAs. The floor-length, sequin dress was an undeniably dazzling choice, as were her long, crystal earrings and wispy updo.

Taylor Swift at the CMAs in 2009

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Perhaps it was just a coincidence, but Swift’s sparkly gold gown at the 2009 CMAs perfectly matched the armful of trophies she went home with that night. The star looked like a real-life princess in the Reem Acra dress that featured a sequined bodice flowing into a chiffon skirt.

Taylor Swift at the 52nd Annual Grammy Awards in 2010

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The singer went full mermaid-glam at the 2010 Grammys in a glittery green off-the-shoulder dress by Kaufman Franco which she accessorized with chunky silver bracelets and a side-swept updo. Later in the evening, she let her blonde curls down as she posed with her awards.

Taylor Swift at the 54th Annual Grammy Awards in 2012

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A true golden goddess, Swift dazzled on the 2012 Grammys red carpet in a cap-sleeved Zuhair Murad gown. Her signature curls were swept back into a neat updo, giving the star a mature, sophisticated look.

Taylor Swift at the Golden Globes in 2013

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Swift began to take her style in a new, sleeker direction with this eggplant-colored Donna Karan gown and low bun at the 2013 Golden Globes. From the front, the star’s dress choice might have seemed simple, but the low back and sheer side panels gave it a sexy edge.

Taylor Swift at the 55th Annual Grammy Awards in 2013

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Taking the Grecian look for a spin, Swift appeared on the 2013 Grammys red carpet in a cream J. Mendel gown with a plunging neckline and metallic details. She kept her jewelry simple and dainty while her hair was styled into a braided updo.

Taylor Swift at the MTV VMAs in 2013

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Old Hollywood glamour was clearly on the menu for Swift in 2013, and that included the VMAs red carpet. The star fully committed to the look by topping off her Hervé Léger by Max Azria dress with a finger-waved bob, red lipstick and sultry eye makeup.

Taylor Swift at the Golden Globes in 2014

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Usually a lover of sparkle, Swift kept it simple and classic for the 2014 Golden Globes in a strapless, two-toned dress by Carolina Herrera. She left her neck bare and instead accessorized with chunky rings and gemstone earrings.

Taylor Swift at the Met Gala in 2014

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Swift’s pale pink Oscar de la Renta gown was so beautiful that even her cats couldn’t resist it. “I’ve never seen more fashionable people lose their composure quicker than when a cat walks up to a satin, custom Oscar de la Renta gown and then decides to make a home inside of it,” the singer told PEOPLE of her pet’s Met Gala antics in 2014.

“She just passed, dug her claws in and started to roll … like when you see a crocodile attack an antelope on National Geographic,” she continued. “That’s what she tried to do to the dress.”

Luckily, Swift and her gown made it to the Gala unscathed — and she looked absolutely stunning.

Taylor Swift at the 57th Annual Grammy Awards in 2015

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Swift took the Grammys red carpet by storm in 2015 with her custom Elie Saab halter dress. For even more bold color, the singer paired the dazzling turquoise dress with matching earrings and bright fuchsia shoes.

Taylor Swift in New York City in April 2015

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The singer’s 2014 move to New York City seemed to spark a new, sophisticated era of her personal style. In April 2015, she was spotted out in a black-and-white blazer and shorts set. She gave the look a pop of color with kelly green heels and a matching purse.

Taylor Swift at the VMAs in 2015

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Swift infamously walked the red carpet with her stylish squad in tow at the 2015 VMAs. The singer donned a sequined houndstooth matching set for the occasion, where she took home the award for video of the year for her hit “Bad Blood.” She accessorized the long-sleeve crop top and high-waisted harem pants with a pair of coordinating metallic pumps.

Taylor Swift in New York City in May 2015

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Swift stepped out in May of 2015 in a vintage-inspired outfit consisting of a sleeveless black top and patterned shorts, which she accessorized with turquoise heels and oversized sunglasses.

Taylor Swift at the Vanity Fair Oscars party in 2016

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Swift looked sleek as ever at the 2016 Oscars afterparty in a black gown with a plunging neckline and high slit by Alexandre Vauthier Haute Couture. According to a rep for the brand, the dress was an archived piece that was never produced. The star’s gold accessories — including a choker necklace and clutch purse — gave the look an ultra-glamorous feel.

Taylor Swift at the 58th Annual Grammy Awards in 2016

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With the help of her striking new bob haircut, Swift stunned at the 2016 Grammys Awards in a brightly colored two-piece ensemble. The custom Atelier Versace look paired an orange-red bandeau top with a fuchsia skirt that featured a daring slit, and the singer accessorized with a choker and strappy metallic heels.

Taylor Swift at the Met Gala in 2016

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Following the Gala’s 2016 theme of Manus x Machina: Fashion in an Age of Technology, Swift wore a metallic silver Louis Vuitton mini dress with a tiered ruffle skirt and cutout waist. Perhaps the most jaw-dropping detail was her new platinum blonde bob, which starkly contrasted her black lipstick.

The look also included black knee-high boots, Eva Fehren rings and an edgy ear cuff.

Taylor Swift at the Billboard Music Awards in 2018

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After a brief hiatus from the red carpet, Swift made her grand return at the 2018 Billboard Music Awards in an ethereal pink gown by Versace that featured a high slit and embellished silver bodice. The star also wore Hueb earrings and shoes by Casadei.

Swift shared the look on Instagram, writing: “My first award show in a few years and it was so much fun thanks to you. I love you guys. PS thanks @versace for this ✨delicate✨ dress.”

Taylor Swift in New York City in 2018

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Even when she’s not glammed up on the red carpet, Swift can still deliver a solid fashion moment. In July 2019, the singer was spotted running around Tribeca in a casual and cool denim crop top and shorts combo, her round sunglasses and red lipstick giving the look her signature feminine flair.

Taylor Swift in New York City in 2019

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Swift again dazzled on the streets of New York in April 2019 when she paired a red houndstooth blazer with a floral slip dress. She accessorized the look with two of her go-tos — her crimson red lips and a bag featuring the face of a cat.

Taylor Swift at the Time 100 Gala in 2019

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On the brink of her colorful Lover era, Swift graced the 2019 Time 100 Gala red carpet in a gorgeous peach and yellow pastel gown by J. Mendel. Her Lorraine Schwartz jewels, dainty headband and romantic updo made the look even more ethereal.

Taylor Swift at the Billboard Music Awards in 2019

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Clearly getting more experimental with her style, Swift wore a lavender ruffled Raisa & Vanessa minidress at the 2019 Billboard Music Awards. She complimented the textured piece with simple Casadei heels and jewels by Stefere and Graziela Gems, Stephen Webster, Moritz Glik and Jenny Dee Jewelry.

Taylor Swift at the MTV VMAs in 2019

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Ahead of her opening performance at the 2019 VMAs, Swift walked the red carpet in a multicolor blazer dress custom-designed by the team at Versace. She also wore black crystal-embellished over-the-knee Christian Louboutin boots, Kallati earrings, a mix of rings by Brumani and Misahara Jewelry and Lorraine Schwartz.

Taylor Swift at the premiere of Cats in 2019

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To celebrate the premiere of the Cats film adaptation, Swift, who starred in the Andrew Lloyd Webber musical, donned a patterned Oscar de la Renta gown as well as her trademark red lipstick. She was later spotted leaving the event with her boyfriend, Joe Alwyn, wearing a navy blue coat over her dress.

Taylor Swift at the Golden Globes in 2020

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For the 2020 Golden Globes, Swift stepped outside of her usual slinky silhouette in favor of something a bit more regal. The star, who was nominated for best original song for “Beautiful Ghosts” from the film adaptation of Cats, wore an Etro navy and yellow silk floral ball gown with a keyhole cut-out, open back, and long flowing train.

To make things even more glamorous, her hair was pulled back into an effortless updo to reveal an eye-catching pair of sapphire drop earrings.

Taylor Swift at the Sundance Film Festival in 2020

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Swift looked all grown up in head-to-toe plaid for the premiere of her documentary Americana at the 2020 Sundance Film Festival. The three-piece Carmen March look featured a bustier-style top, pleated pants, and an overcoat, but the pattern frenzy didn’t stop there — even her pointed-toe boots were plaid.

Taylor Swift at the 63rd Annual Grammy Awards in 2021

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Swift’s floral embroidered dress by Oscar de la Renta for the 2021 Grammys seemingly paid homage to her album folklore, which won the singer her third Album of the Year award that evening.

On Twitter, the fashion house gave a behind-the-scenes look at the making of the garment, which involved the botanical appliqués being sewed on individually. Along with the dress, which retailed for $8,990, Swift also wore a pair of Louboutin heels and Cathy Waterman jewelry to walk the red carpet and donned a stylish matching floral face mask when necessary.

Taylor Swift at the premiere of All Too WellThe Short Film in 2021

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Given her penchant for dresses and skirts, it was somewhat unexpected to see Swift in a suit at the premiere of her short film, All Too Well. However, the purple velvet jacket and pants looked tailor-made for the star, and the black lapels and brass buttons were stunning details.

Taylor Swift at the Tribeca Film Festival in 2022

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Continuing on her recent menswear kick, Swift donned a navy pinstripe pantsuit for a screening of her short film at the 2022 Tribeca Film Festival. Rather than a jacket, the singer opted for a vest which she paired with pleated pants and a pair of red heels.

Taylor Swift at the MTV VMAs in 2022

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Swift made a grand return to the VMAs in August 2022 in a dazzling Oscar de la Renta minidress. She paired the sparkling number with matching Christian Louboutin heels and Lorraine Schwartz jewelry.

The singer’s crystal-covered outfit wasn’t the only thing that made headlines at the event — Swift also announced her brand-new album that’s set to release in October while accepting the video of the year award.

Taylor Swift at the MTV Europe Music Awards in 2022

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The Midnights singer turned heads on the red carpet at the 2022 MTV Europe Music Awards in Duesseldorf, Germany. The singer wore a revealing David Koma ensemble, which included a black bodysuit with a bejeweled chain-link patterned skirt. She accessorized the look with a pair of black Giuseppe Zanotti sandals.

Taylor Swift at the 65th Annual Grammy Awards in 2023

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Swift arrived at the 2023 Grammys in a dark blue, long-sleeved crop top and matching floor-length skirt by Roberto Cavalli.

As if the crystal-embellished ensemble wasn’t enough, the singer paired the sparkly two-piece with $3 million of worth Lorraine Schwartz jewelry, including sapphire earrings and multiple rings.