Taylor Swift’s Best Red Carpet Moments

01 of 67

Taylor Swift at the 2023 VMAs

Taylor Swift at the 2023 MTV Video Music Awards — Gilbert Flores/Variety via Getty Images

Taylor Swift smoldered in Versace at the most recent MTV Video Music Awards. The look was giving, “Yeah, I’m currently on the highest grossing tour of all time.”

02 of 67

Taylor Swift at the 2023 Grammys

Taylor Swift on the red carpet for the 65th Grammy Awards — Allen J. Schaben / Los Angeles Times via Getty Images

In a nod to her tenth studio album, Midnights, Swift looked every bit like midnight rain in this glittering two-piece navy set by Roberto Cavalli. She complemented it with bejeweled earrings courtesy of Lorraine Schwartz.

03 of 67

Taylor Swift at the 2022 MTV EMAs

Taylor Swift attends the red carpet during the MTV Europe Music Awards 2022 — Kate Green/Getty Images for MTV

Swift was also in her “bejeweled” era at the 2022 EMAs. The singer wore a custom David Koma look which featured a black bodysuit and a custom chainmail-style overlay. To pull the look together, she went for a green smokey eye.

04 of 67

Taylor Swift at the 2022 VMAs

Taylor Swift at the 2022 MTV Video Music Awards — Bryan Bedder/Variety via Getty Images

Pre-Midnights, Swift got fans ready for what was to come with an Oscar de la Renta halterneck mini dress. Her Louboutin sandals matched the vibe—they were shiny silver with a T-strap and some hanging crystals.

05 of 67

Taylor Swift in the VMAs Press Room 2022

Taylor Swift in the press room at the 2022 MTV Video Music Awards — Christopher Polk/Variety via Getty Images

Posing with her awards for Video of the Year, Best Direction, and Best Longform Video, Taylor shifted into another midnight moment: She wore a shimmering blue Moschino romper decorated with stars that evoked the midnight sky. Completing the look, she draped a white faux fur coat over her shoulders and added even more sparkle with glittery silver platforms.

06 of 67

Taylor Swift at the 2022 AMAs

Taylor Swift on the carpet for the 2022 American Music Awards — Gilbert Flores/Variety via Getty Image

In 2022, Swift solidified her status as the most-awarded artist in American Music Awards history. On that memorable night, she won all six awards for which she was nominated. Beyond securing Artist of the Year, she also won Favorite Country Album, Favorite Pop Album, and Favorite Music Video for her 2022 Red (Taylor’s Version) re-release. Furthermore, Swift was recognized as Favorite Female Pop Artist and Favorite Female Country Artist. Embodying her golden status at the AMAs, she radiated in a backless gold jumpsuit designed by The Blonds.

07 of 67

Taylor Swift Attends the 'All Too Well' Premiere

Dylan O'Brien, Taylor Swift and Sadie Sink on the carpet for the — ANGELA WEISS/AFP via Getty Images

Taylor Swift was spotted at the premiere alongside Sadie Sink and Dylan O’Brien, the stars of her short film All Too Well. She wore a velvet red Etro suit, fitting given the album title—Red (Taylor’s Version)—and paired it with stylish ankle boots by Alexandre Birman.

08 of 67

Taylor Swift at the Toronto Film Festival

Taylor Swift on the red carpet at 'In Conversation With... Taylor Swift' — Amy Sussman/Getty Images

At the 2022 Toronto International Film Festival, Swift turned heads during a special screening of All Too Well: The Short Film, stepping out in a custom sequined gown by Louis Vuitton.

09 of 67

Taylor Swift at the 2021 Grammys

Taylor Swift on the red carpet at the 63rd Annual Grammy Awards — Jay L. Clendenin / Los Angeles Times via Getty Images

Behold a history-making outfit: a semi-sheer floral mini dress by Oscar de la Renta paired with perfect pink Christian Louboutin sandals. Swift stole the spotlight at the 2021 Grammys, winning Album of the Year for Folklore, her eighth record. This win marked her as the first woman to secure the award three times.

10 of 67

Taylor Swift Attends the 'Miss Americana' Premiere

Taylor Swift on the carpet for the Netflix premiere of Miss Americana — Kevin Mazur/Getty Images for Netfilx

At the Sundance Film Festival premiere of her documentary, Miss Americana, Swift was all about the business. The superstar donned a stylish houndstooth ensemble complete with a belted jumpsuit, coordinating coat, and matching printed boots.

11 of 67

Taylor Swift at the 2020 Golden Globes

Taylor Swift photographed on the red carpet of the 77th Annual Golden Globe Awards — P. Lehman/Future Publishing via Getty Images

Nominated for the best original song “Beautiful Ghosts” from Cats, Swift graced the Golden Globes carpet in a fabulous floral Etro gown. While she was a vision to behold, the buzz was also around whether the public would get a glimpse of her partner at the time, Joe Alwyn. The seldom-seen couple opted out of the carpet but were spotted together inside the show.

12 of 67

Taylor Swift at the Cats Premiere

Taylor Swift on the carpet for the world premiere of "Cats" — Steven Ferdman/Getty Images

Having contributed the song "Beautiful Ghosts" to the soundtrack, Swift made an appearance at the New York City premiere of Cats in a breathtaking Oscar de La Renta dress. This ruby floral fil coupé satin gown is priced at a cool $17,990 online. But hey, it had pockets!

13 of 67

Taylor Swift at the Billboard Women in Music Event 2019

Taylor Swift on the carpet at the Billboard Women In Music 2019 — Emma McIntyre/Getty Images for Billboard

Taylor Swift became the first-ever recipient of Billboard's Woman of the Decade Award at the 2019 Billboard Women in Music Event. She chose another Oscar de la Renta ensemble for the occasion, but instead of her usual feminine florals, she opted for a sleek jumpsuit with gold embellishments.

14 of 67

Taylor Swift at the 2019 AMAs

Taylor Swift on the red carpet at the 2019 American Music Awards — Kevin Mazur/Getty Images for dcp

Another big win to add to the resume for Ms. Swift. At the 2019 American Music Awards, she was honored with the Artist of the Decade prize. Turning heads on the carpet, she donned a custom sparkly green dress by Julien MacDonald, complemented by knee-high black boots and gunmetal jewelry.

15 of 67

Taylor Swift Attends the 2019 VMAs

Taylor Swift attends the 2019 MTV Video Music Awards red carpet — Aaron J. Thornton/Getty Images

At the 2019 MTV VMAs, where she won the Video of the Year award, the singer turned heads in Versace. Swift sported a multicolored blazer showcasing Versace’s signature Medusa print and adorned with rainbow crystals. Underneath, a vibrant hot-pink mini dress shimmered in complement. She finished off the ensemble with sparkly over-the-knee Christian Louboutin boots and glittering green hoops from Lorraine Schwartz.

16 of 67

Taylor Swift at the TCAs 2019

Taylor Swift arrives on the blue carpet at TEEN CHOICE 2019 — FOX Image Collection via Getty Images

At the 2019 Teen Choice Awards, Taylor Swift received the inaugural Icon Award. She donned a distinctive Versace ensemble that she clearly loved, because she sported a similar look to the 2019 VMAs. Embracing the brand's bold aesthetic, the outfit was a vividly printed short suit. Swift complemented the look with a splash of color, choosing bright orange heels by Kat Maconie.

17 of 67

Taylor Swift Attends the 2019 Billboard Music Awards

Taylor Swift on the red carpet at the 2019 Billboard Music Awards — Jeff Kravitz/FilmMagic for dcp

This purple pastel moment was another nod to Swift's super-sweet Lover era. The singer graced the 2019 Billboard Music Awards red carpet in a ruffled lavender dress by Raisa Vanessa.

18 of 67

Taylor Swift at the TIME 100 Gala 2019

Taylor Swift on the red carpet at the TIME 100 Gala Red Carpet — Dimitrios Kambouris/Getty Images for TIME

Ah, the buildup to the Lover era. Swift attended the 2019 TIME 100 Gala in a pale pink-and-yellow gown by J. Mendel. The singer was deep into a pastel theme that year, as this look mirrored the cotton-candy hues saturating her Instagram and videos. Unbeknownst to us at that time, the Lover era was on the horizon.

19 of 67

Taylor Swift at the iHeartRadio Music Awards 2019

Taylor Swift on the red carpet at the 2019 iHeartRadio Music Awards — Rich Polk/Getty Images for iHeartMedia

A high-low queen! At the 2019 iHeartRadio Music Awards, Swift rocked a shiny iridescent romper by Rosa Bloom. Can you believe it was only $246? Such a steal! But those Sophia Webster shoes? They rang in at $595—so, yeah, emphasis on the “high-low” part.

20 of 67

Taylor Swift Attends the 2019 Golden Globes Afterparty

Taylor Swift on the red carpet at the 2019 InStyle and Warner Bros. 76th Annual Golden Globe Awards Post-Party — Matt Winkelmeyer/Getty Images for InStyle

After months away from the formal award-show scene, Swift's return did not disappoint. She graced the 2019 InStyle and Warner Bros. 76th Annual Golden Globe Awards Post-Party in a stunning black Versace gown.

21 of 67

Taylor Swift at the 2018 AMAs

Taylor Swift on the red carpet at the 2018 American Music Awards — Kevin Mazur/Getty Images For dcp

T-Swift gave off disco-ball vibes at the 2018 AMAs. (Or should we say "mirrorball"? Was she hinting at what was coming next on her 2020 Folklore album?) She shone in a sparkly metallic Balmain minidress, paired perfectly with matching thigh-high boots.

22 of 67

Taylor Swift at the Billboard Music Awards 2018

Taylor Swift on the red carpet at the 2018 BBMA's — Brian Friedman/NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images

This outfit marked Taylor's red-carpet comeback. Before hitting the 2018 Billboard Music Awards carpet, she'd been MIA from award shows for two years. She marked her return with an ultra feminine Versace dress, a clear shift from her then-edgy style. But true to form, she rocked a snake ring as a nod to her Reputation era.

23 of 67

Taylor Swift at the 2016 Met Gala

Taylor Swift on the red carpet at the "Manus x Machina: Fashion In An Age Of Technology" Costume Institute Gala — Rabbani and Solimene Photography/Getty Images

Fresh off debuting her bleach-blonde bob, Swift stepped onto the Met Gala red carpet in 2016. That year wasn't just any appearance for her, however: she served as co-chair for the event, themed "Manus x Machina: Fashion in an Age of Technology." Staying true to the techy vibe, she rocked a futuristic, cut-out metallic dress by Louis Vuitton, perfectly paired with lace-up sandals.

24 of 67

Taylor Swift at the BMI Pop Awards 2016

Taylor Swift on the red carpet at the 64th Annual BMI Pop Awards — Steve Granitz/WireImage

At the 2019 BMI Pop Awards, Taylor Swift was honored with a prize named after her: the "Taylor Swift Award." This special accolade celebrated her unparalleled artistic talent and influence. The BMI has only ever created an award in an artist's name once before, and that was for Michael Jackson in 1990. Embracing her edgier phase — which was also evident at the Met Gala — Swift chose a gothic velvet gown by Monique Lhuillier and complemented it with a striking black-diamond choker.

25 of 67

Taylor Swift at the 2016 iHeartRadio Music Awards

Taylor Swift on the red carpet at the 2016 iHeartRadio Music Awards — Frazer Harrison/Getty Images for iHeartRadio / Turner

Bringing major sequined-Sandy-from-Grease vibes, T-Swift rocked a skin-tight black sequin jumpsuit designed by Hedi Slimane for Saint Laurent.

26 of 67

Taylor Swift at the 2016 Grammys

Taylor Swift on the red carpet for THE 58TH ANNUAL GRAMMY AWARDS — Trae Patton/CBS via Getty Images

The look is iconic. The bob was bobbing and the colors were oh-so-fabulous. Taylor wore a stunning sherbert two-piece by Atelier Versace to the 2016 Grammy Awards.

27 of 67

Taylor Swift Attends the 'Vanity Fair' Oscars Afterparty 2016

Taylor Swift on the red carpet for the 2016 Vanity Fair Oscar Party — Anthony Harvey/Getty Images

One of Swift's sexiest looks to date, she turned heads in a jaw-dropping black Alexandre Vauthier gown featuring a plunging neckline and a daring high slit. Her golden accessories, from Giuseppe Zanotti shoes to a coordinating Jimmy Choo clutch, added the right amount of glam. And let's not forget that freshly snipped bob to round off the look.

28 of 67

Taylor Swift at the 2015 VMAs

Taylor Swift arrives on the red carpet at the MTV Video Music Awards — MARK RALSTON/AFP via Getty Images

For the 2015 VMAs, Swift made the case for “comfy on the carpet.” That’s right, the singer showed up in sweats….well, sorta. She wore an Ashish two-piece sequin sweatsuit, dialing up the glam factor with bold eyeliner and statement Christian Louboutin heels to prove this look was more couture than couch.

29 of 67

Taylor Swift at the 2015 Billboard Music Awards

Taylor Swift on the red carpet at the 2015 Billboard Music Awards — Jon Kopaloff/FilmMagic

Swift turned heads in this sparkly white cutout jumpsuit courtesy of Balmain. The star attraction? Her custom “Bad Blood” clutch, and the fact that she showed up with her “Bad Blood” crew. For a refresh, members included Zendaya, Gigi Hadid, and Selena Gomez, just to name a few.

30 of 67

Taylor Swift at the iHeartMusic Radio Awards 2015

Taylor Swift on the red carpet at the 2015 iHeartRadio Music Awards — Jon Kopaloff/FilmMagic

An edgy twist on Swift’s beloved sparkly mini dresses. This particular number by Kaufman Franco showcased sultry cutouts, shimmering brilliantly on the iHeartRadio Music Awards carpet.

31 of 67

Taylor Swift at the BRIT Awards 2015

Taylor Swift on the red carpet for the BRIT Awards 2015 — Samir Hussein/WireImage

Taylor Swift wowed in a dramatic dragon dress by Roberto Cavalli as she attended the 2015 BRIT Awards.

32 of 67

Taylor Swift at the 2015 Elle Style Awards

Taylor Swift on the red carpet for the ELLE Style Awards — Fred Duval/FilmMagic

Usually known for her sweet ensembles, Swift turned heads in a sultry, lingerie-inspired look. With its intricate lace detailing, this unexpected Julien MacDonald number made quite the impact.

33 of 67

Taylor Swift at the Grammys 2015

Taylor Swift on the red carpet for The 57th Annual GRAMMY Awards — Jason Merritt/Getty Images

At the 57th Grammy Awards, Swift dazzled in a teal ombre gown by Elie Saab. The dress — with its front slit revealing a mini skirt — perfectly showcased her purple Giuseppe Zanotti sandals.

34 of 67

Taylor Swift at the Victoria’s Secret Fashion Show 2014

Taylor Swift on the red carpet for the 2014 Victoria's Secret Fashion Show — Anthony Harvey/Getty Images for Victoria's Secret

Following her show-stopping performance at the 2014 Victoria's Secret Fashion Show, Swift graced the pink afterparty carpet in Zuhair Murad couture. Donning a sultry white gown with a crystal-embellished bodice and long sleeves, she looked every bit the VS Angel herself.

35 of 67

Taylor Swift Attends the 2014 AMAs

Taylor Swift on the red carpet for the 2014 American Music Awards — Jason LaVeris/FilmMagic

Typically a fan of sparkles and embellishments, Swift took an uncharacteristic turn for the 2014 AMAs. The "Blank Space" singer graced the carpet in a super-simple green Michael Kors gown and no accessories.

36 of 67

Taylor Swift at the VMAs 2014

Taylor Swift on the red carpet for the 2014 MTV Video Music Awards — C Flanigan/Getty Images

Taylor has a clear love for a mini-short moment, and with those mile-long legs, who could blame her? At the 2014 VMAs, Swift flaunted her gams in a Mary Katrantzou printed romper.

37 of 67

Taylor Swift at the 2013 AMAs

Taylor Swift on the red carpet for the 2013 American Music Awards — Larry Busacca/AMA2013/Getty Images for DCP

All that glittered was most definitely gold when it came to Taylor Swift’s outfit at the 2013 AMAs. The superstar sparkled in a sexy Julien MacDonald sequined minidress, complemented by a voluminous blowout, metallic makeup, and coordinating platform heels.

38 of 67

Taylor Swift at the 2013 VMAs

Taylor Swift on the red carpet for the 2013 MTV Video Music Awards — Lars Niki/Corbis via Getty Images

A decade before its release, Swift channeled a “Midnight Rain” vibe in her ensemble. She wore a navy Hervé Léger by Max Azria dress adorned with shimmering black embellishments. Complementing the look, Swift opted for a retro Hollywood-inspired updo and a sultry, vampy lip.

39 of 67

Taylor Swift at the 2013 Billboard Music Awards

Taylor Swift on the red carpet for the 2013 Billboard Music Awards — ROBYN BECK/AFP via Getty Images

This long-sleeved sequin minidress, paired with a high pony and platform sandals, is peak 2013. Though we might blink at this mid-aughts fashion memory, back then, this Zuhair Murad ensemble was the height of style.

40 of 67

Taylor Swift Attends the 2013 Met Gala

Taylor Swift on the red carpet for the 'PUNK: Chaos to Couture' exhibition at the Metropolitan Museum of Art — Lars Niki/Corbis via Getty Image

Swift nailed the "PUNK: Chaos to Couture" theme at the 2013 Met Gala, donning a striking J. Mendel gown.

41 of 67

Taylor Swift at the 2013 ACMs

Taylor Swift on the red carpet for the 48th Annual Academy of Country Music Awards — Frazer Harrison/ACMA2013/Getty Images for ACM

Taylor did what she does best: rock a glittering gown. For the 2013 ACM awards, she chose a sparkly beaded dress by Dolce & Gabbana.

42 of 67

Taylor Swift at the BRIT Awards 2013

Taylor Swift on the red carpet for the 2013 Brit Awards — Mike Marsland/WireImage

At the 2013 BRIT Awards, where she performed “I Knew You Were Trouble,” Taylor Swift stunned on the red carpet in a black Elie Saab gown. The dress featured dual thigh-high sheer panels that gave the floor-length skirt a sultry edge. A gold belt with link detail cinched her waist, emphasizing her svelte figure.

43 of 67

Taylor Swift at the 2013 Grammys

Taylor Swift on the red carpet at the 55th Annual GRAMMY Awards — Lester Cohen/WireImage

Channeling a Grecian goddess at the Grammys, Taylor Swift graced the red carpet in a creamy J.Mendel chiffon gown paired with a beautifully braided up-do.

44 of 67

Taylor Swift at the 2013 Golden Globes

Taylor Swift on the red carpet at the 70th Annual Golden Globe Awards — Christopher Polk/NBC/NBCUniversal via Getty Images

Taylor Swift looked Old Hollywood glam in this eggplant gown with matching earrings and a chic updo.

45 of 67

Taylor Swift Attends the People's Choice Awards 2013

Taylor Swift on the red carpet for the 39th Annual People's Choice Awards — Frazer Harrison/Getty Images for PCA

After her high-profile split from Harry Styles, Swift made a statement at the 2013 People’s Choice Awards in her version of a “revenge dress.” She stunned in a white Ralph Lauren gown with a daring plunging neckline, while ice-blue statement earrings provided a splash of color.

46 of 67

Taylor Swift at the 2013 AMAs

Taylor Swift on the red carpet for the 40th American Music Awards — Christopher Polk/AMA2012/Getty Images for AMA

Swift brought a bit of sparkle to the AMAs red carpet in a shimmering long-sleeved mini dress by Zuhair Murad. She paired the metallic number with coordinating heels and standout Neil Lane earrings.

47 of 67

Taylor Swift at the 2013 EMAs

Taylor Swift on the red carpet at the MTV EMA's 2012 — Ian Gavan/Getty Images for MTV

For the 2012 EMAs, Taylor went retro in this 1920s-inspired beaded gown by J. Mendel. She complemented the look with a sultry smokey eye and tousled waves.

48 of 67

Taylor Swift at the 2013 CMAs

Taylor Swift in the red carpet at the 46th Annual CMA Awards — Sara Kauss/Disney General Entertainment Content via Getty Images

RED era hive, rise! T-Swift stunned on the CMAs red carpet in this beautiful beaded floral dress by Jenny Packham. She added a matching bold red lip, her signature during this period.

49 of 67

Taylor Swift at the 2013 VMAs

Taylor Swift on the red carpet at the 2012 MTV Video Music Awards — Kevin Mazur/WireImage

Switching things up from her go-to sparkly style, Taylor opted for a sleek look at the 2012 VMAs. She rocked a creamy J. Mendel suit, perfectly accented with Lorraine Schwartz earrings.

50 of 67

Taylor Swift Attends the Billboard Music Awards 2012

Taylor Swift on the red carpet at the 2012 Billboard Music Awards — Kevin Mazur/WireImage

Another big moment in her RED era, Taylor graced the 2012 Billboard Music Awards red carpet in a dreamy red chiffon number by Elie Saab.

51 of 67

Taylor Swift at 2012 ACMs

Taylor Swift on the red carpet at the 47th Annual Academy Of Country Music Awards — Christopher Polk/ACMA2012/Getty Images for ACM

Swift radiated elegance in a white J. Mendel column dress, accented with metallic details, while bagging the Entertainer of the Year title. Her sultry look, enhanced by smokey eyes and relaxed, wavy hair, was both sexy and sophisticated.

52 of 67

Taylor Swift Attends 'The Lorax' Premiere in 2012

Taylor Swift and Zac Efron on the red carpet for — Kevin Winter/Getty Images

This photo is textbook-worthy! Taylor Swift and Zac Efron strike a pose at the 2012 premiere of The Lorax movie.

53 of 67

Taylor Swift at the 2012 Grammys

Taylor Swift on the red carpet for The 54th Annual GRAMMY Awards — Jeff Vespa/WireImage

Doing what she does best: winning Grammys in sparkly gowns. That year, Swift won two awards — Best Country Solo Performance and Best Country Song — all while shining in a Zuhair Murad masterpiece.

54 of 67

Taylor Swift at the 2011 CMAs

Taylor Swift on the red carpet at The 45th Annual CMA Awards — Jason Kempin / Disney General Entertainment Content via Getty Images

At the 2011 Country Music Awards, Taylor Swift nabbed the title of Entertainer of The Year. The then-21-year-old sensation paired her J. Mendel gown perfectly with Christian Louboutin heels and some sparkling pieces from Lorraine Schwartz.

55 of 67

Taylor Swift at the Teen Choice Awards in 2011

Taylor Swift on the red carpet at the 2011 Teen Choice Awards — Frank Trapper/Corbis via Getty Images

A little Marilyn moment for the 2011 TCAs. And let’s talk about this blue eyeshadow…we die.

56 of 67

Taylor Swift’s Look at the Billboard Music Awards 2011

Taylor Swift on the red carpet at the 2011 Billboard Music Awards — Kevin Mazur/WireImage

At the 2011 BBMAs, T-Swift shone in this Elie Saab number. She not only made a fashion statement, but also took home accolades for Top Billboard 200 Artist, Top Country Artist, and Top Country Album.

57 of 67

Taylor Swift at the 2011 Golden Globes

Austin Swift and singer Taylor Swift on the red carpet at the 71st Annual Golden Globe Awards — Alberto Rodriguez/NBC/NBCUniversal via Getty Images

Up for best original song for “One Chance,” the singer gave her typical sparkly, girly-glam style a break. She turned heads in a dramatic red Carolina Herrera Pre-Fall 2014 strapless gown, accentuated with an edgy black trim along the neckline. And the cherry on top? She had her brother, Austin, by her side as her date.

58 of 67

Taylor Swift at the AMAs in 2010

Taylor Swift on the red carpet for the 2010 American Music Awards — Steve Granitz/WireImage

We were thick in the curly-hair Taylor era at this point, so this pin-straight hair was a moment.

59 of 67

Taylor Swift Attends the 2010 Met Gala

Taylor Swift on the red carpet for the "American Woman: Fashioning A National Identity" Costume Institute Gala at The Metropolitan Museum of Art — LAN/Corbis via Getty Images

At the 2010 Met Gala, with the theme “American Woman: Fashioning a National Identity,” Taylor channeled Old Hollywood glamor. With a white Ralph Lauren Spring 2005 gown paired with a classic bob and bold red lips, she nailed the theme.

60 of 67

Taylor Swift at the 2010 Grammys

Taylor Swift arrives on the red carpet at the 52nd Grammy Awards — GABRIEL BOUYS/AFP via Getty Images

This navy glittering gown by Kaufman Franco is the definition of “Midnight Rain,” but the curly updo screams “Fearless Era.”

61 of 67

Taylor Swift at the 2009 CMAs

Taylor Swift on the red carpet for The 43rd Annual CMA Awards — Donna Svennevik/Disney General Entertainment Content via Getty Images

At peak "Fearless Era," Taylor shone in a Reem Acra number at the 2009 CMA Awards. At just 19, she won all four awards she was up for: Music Video, Album, Female Vocalist, and the evening's pinnacle, Entertainer of the Year. As the youngest recipient of the E.O.T.Y. title, she made country-music history.

62 of 67

Taylor Swift Attends the 2009 VMAs

Taylor Swift on the red carpet for the 2009 MTV Video Music Awards — Kevin Mazur/WireImage

The INFAMOUS 2009 VMAs, truly a pop culture landmark. But let's focus on the fashion rather than the drama. A 19-year-old Swift, radiant in a Kaufman Franco dress, walked away with the Best Female Music Video of the Year award.

63 of 67

Taylor Swift at the 2009 Grammys

Taylor Swift on the red carpet for the 51st Annual GRAMMY Awards — Kevin Mazur/WireImage

Swift took a brief departure from the sequins and opted for this sexy-yet-understated black gown by Kaufman Franco.

64 of 67

Taylor Swift at the 2008 AMAs

Taylor Swift on the red carpet for the 2008 American Music Awards — Kevin Mazur/WireImage

Ahhh, it's 2008. Taylor Swift's curls are in full bounce, and she's donning a metallic mini with matching peep-toe pumps on the red carpet. Life is good.

65 of 67