Taylor Swift is the prime example of a new millennium pop superstar. She, along with her contemporaries Justin Bieber and Lady Gaga, showcases the current generation’s eccentricities that made them so relatable to millennials in the first place. With Justin, it was his rise to fame through the website YouTube that makes him such a millennial icon. With Lady Gaga, it’s her millennial take on the liberated Madonna (so there are more hints of social justice and liberal ideas in her music) with a slight hint of the anti-establishment, anti-fashion Bjork. Taylor Swift was originally a country singer in the same vein as Trisha Yearwood and LeAnn Rimes who turned full-on pop stars (or even Miley Cyrus). She’s also reminiscent of Katy Perry, who herself was originally a religious singer turned liberal icon and social justice pop singer with an emphasis on feminism and women power. Originally from Pennsylvania before moving to Nashville, Tennessee, Taylor was interested in music and poetry at a young age. She even won a nationwide contest at 9 years old for the cute poem “Monster in my Closet.” She then sang the national anthem at 11 years old for the U.S. Open tennis tournament. Finally, at 14 years old, she was signed by Sony/ATV. Taylor then “swiftly” broke into the Top 40 Pop Hits in 2006 with “Tim McGraw,” her debut single.
Soon after, she achieved success and mainstream appeal both in the country music world and mainstream pop. With that said, here are her top red carpet looks as part of the new millennium’s current crop of music royalty.
18. She Went For Bold Color Blocking At The 2016 Grammys
Now as far as the Grammys go, this is more familiar territory to Taylor Swift. She’s practically the queen of the Grammys like Whitney Houston and Mariah Carey before her. After all, every one of her biggest hits has crossed over to the mainstream massively. Furthermore, four of her pop albums, including 1989, went on to achieve No. 1 on the Billboard 200. The lithe blonde small-town Pennsylvanian girl also earned all seven Grammys of hers throughout her career filled with two EPs and five albums (at the time of this writing). She’s a millennial that has earned her accolades, so it is only appropriate that in the 58th Annual Grammy Awards, she’d end up strutting out her stuff with her ostentatious ensemble dress that really showcases how she normally stands out from the crowd. She wore a Versace ensemble featuring an orange cropped top paired with a fuchsia pink skirt with center slit.
17. Looking Cute In Black And White At The ACM Awards In 2014
Taylor isn’t only the queen of the Grammys. She also gets to make her statement even at present at the ACM or American Country Music Awards. After all, she has certified country singer credibility with all four of her country albums ending up as No. 1 on the country charts as well as getting seven No. 1 singles on the country charts. At the ACM Awards 2014, she sported a chic ensemble by J. Mendel, featuring a white crop top and a slitted skirt.
Taylor arguably has not betrayed her country roots at all. If anything, she remains beloved in the country music scene even as she anchored herself into pop music success since getting No. 1 on the Hot 100 for the hit 2012 single “We Are Never Getting Back Together.” Also, dozens of her songs after that ended up charting on the Hot 100 (almost all of her songs made it to the Top 40 at that).
16. Sultry In Black At The Brit Awards In 2013
Even the British love them some Taylor Swift. She wears a simple and elegant black Elie Saab dress that’s daring in the right places, showing some showgirl leg with long sheer leg panels. It probably helped that there were rumors of an Ed Sheeran and Taylor Swift romance back in 2013 (Ed eventually got engaged to long-time girlfriend Cherry Seaborn). Ed and Taylor also had collaborative songs like 2018’s “End Game” and 2012’s “Everything Has Changed,” which helped endear Taylor to a British audience (or perhaps it’s the other way around and Ed became more popular after becoming featured in many a Taylor Swift song). Regardless, Brits will probably view Taylor favorably even without the Sheeran connection and even though they’d probably cheer Adele over her (since the English singer and songwriter, like Ed, is one of their own).
15. Looking Like A Full-On Disney Princess At The 2015 Grammys
Speaking of the Grammys once again, Taylor made waves in the 2015 Grammy Awards or the 57th Annual Grammy Awards with a fabulous teal ombre dress worthy of a Disney Princess. She looks like a true winner on the Grammys’ red carpet with a dress that’s appropriate of her stature as the most commercially successful country artist of all time (as certified by Nielsen itself). This means she has surpassed the likes of legends like Garth Brooks, George Strait and Shania Twain (although these are more strictly country singers who top the country charts more often than not save for Shania, who actually also got mainstream pop radio play). This pop diva with the gem-colored dress has also single-handedly made independent Big Machine Records label and producer Nathan Chapman big names in the country music industry.
14. Looking Like A Goddess At The Grammys In 2013
As for the 2013 Grammy Awards or the 55th Annual Grammy Awards, Taylor dazzled audiences and the press with her J. Mendel all-white gown and the fact that she was able to win the award for Best Song Written for a Motion Picture, Television or Other Visual Media (“Safe & Sound” as part of the popular Hunger Games soundtrack). She was also nominated for Record of the Year and Best Country Duo/Group Performance. Her immaculately clean dress epitomizes what proved to be a glorious night for her. Then again, winning awards at the Grammys is almost like Tuesday for her as well; it’s something that’s par for the course for the pop princess with country music credentials. Regardless, even though the extraordinary has become ordinary for her, she still shines in all her diva glory with a brand name dress to match her immeasurable talents.
13. Red Made Her Face Pop At The 2017 CMA Awards
At last year’s Country Music Awards, Taylor grabbed eyeballs with her beaded floral embroidered ball gown that’s as red as blood or rubies. Although at heart, Miss Swift is as goofy as Jennifer Lawrence (with J-Law being described as the geeky girl stuck in a prom queen’s body), she’s able to go from goofy to glamorous when walking the red carpet. Actually, in many ways, the country singer turned pop superstar is instead a variant of J-Law in that she has an awkward geek girl’s mannerisms and body that just happened to have a pop diva’s powerful voice and versatile musicality. Like Lisa Loeb with Mariah Carey sensibilities. Or like something out of a movie like She’s All That. Maybe she’s more like the country girl turned pop star that Miley Cyrus portrayed back in her hit Disney Channel TV show Hannah Montana. Funnily enough, Taylor appears as herself in Hannah Montana: The Movie. As the song goes, Taylor’s got the best of both worlds.
12. Looking Like A VS Supermodel At The Victoria’s Secret In 2014
While in her music videos, Taylor is able to portray the overly tall nerd girl perfectly (just add glasses and prosthetic teeth), her amazing red carpet transformations are enough to make you second guess who you’re looking at. She’s able to transform repeatedly during these special events – like a true pop diva who’s used to performing on stage. This time around, she’s wearing an extremely revealing white dress with a see-through embroidered right sleeve and top that makes her blend in with the rest of the Victoria’s Secret models. The same “gangly” limbs of hers that would’ve made her the awkward “ugly duckling” in high school serve her well on the red carpet, turning her into one of the waif-like, gazelle-like runway models there. No wonder she was able to portray both the nerd and the popular girl in her music video “You Belong to Me.” That’s Taylor’s secret when it comes to her versatile looks.
11. Channelling Hillary Clinton At The 2012 VMAs
Ah, yes. The Elephant in the Room will finally be addressed. In the Video Music Awards 2012, Taylor put on a white pantsuit ensemble that would’ve made Hillary Clinton proud and showcased her waif-thin model body along with her gorgeous blonde features. However, the 2012 VMAs is actually three years removed from an infamous incident involving Taylor and a certain Mr. Kanye West. Back at the 2009 VMA, in one of the most infamous moments in VMA History, a beaming Taylor won Best Female Video for “You Belong with Me” over Beyonce’s “Single Ladies (Put a Ring on It).” While wearing a lovely sequined dress, Swift’s acceptance speech was interrupted by Kanye, who proclaimed, “Yo Taylor, I’m really happy for you, I’ll let you finish, but Beyonce has one of the best videos of all time. One of the best videos of all time!” The feud between Kanye and Taylor has been going on ever since, with Kanye even proclaiming that he made her famous in his song “Famous.”
10. Red Looked Beautiful On Her At The 2012 Billboards Awards
Taylor would make an excellent “Woman in Red” that’s supposed to distract Neo during a virtual reality simulation in the movie The Matrix. Sure, she lacks the curvaceous “va-va-voom” body of someone like Marilyn Monroe or Anna Nicole Smith. However, she actually has more of a Kate Moss or Twiggy body that became all the rage among models from the swinging 60s all the way to the 90s and beyond. She’s tall for a woman, and her build allows her to showcase flowing dresses like the one she wore to the Billboards Music Awards. It also helps that she has such beautiful Goldilocks blonde hair that has never gone out of style in Hollywood and the music industry at large. She’s indeed a good-looking young woman with a powerful voice and immense creativity.
9. Going Bold With A Cool Design At The 2014 Brit Awards
This time around, Taylor comes out swinging with an unforgettable black gown with red dragon design. She knows how to dress in accordance to her audience, at least. Every time she’s out to perform at award shows like the Brit Awards, she knows how to dial down her fashion at the appropriate levels, hence her classier appearance at this particular event. Her coiffed 90s Princess Di hairdo most certainly completed her look in a good way. Up front, her dress looks straightforward and quite formal. However, its hidden depths and beauty can be seen from behind, where the dragon design is most apparent. The see-through threads at her back showcase some tasteful amount of skin from behind as well. Taylor looks fierce and gorgeous in this Dragon Dress of hers. It’s therefore a shame that this is probably the last time she’ll wear it, since wearing the same thing twice at award shows is an unsaid faux pas. Hopefully, her 2015 hairstyle can return in the future regardless.
8. Looking Angelic In A White Dress At The ACM Awards In 2012
Taylor looks great in her signature bangs when she lets her hair down. Although her Princess Di look along with her Dragon Dress at the 2015 Brit Awards three years later is arguably better, this hairdo is far more appropriate with her white dress with gold trim that showcases a bit of skin on her sides and her underrated curves. While her overall body type is comparable to Twiggy in her prime or the typical gazelle-like runway model, Taylor does have an hourglass figure of her own that doesn’t get featured enough. Her hips are regularly featured in many of her form-fitting dresses and gowns, more so now than in previous ones. This is probably one of her most alluring dresses yet. This just goes to show that you don’t need plunging necklines or less fabric to exude femininity and pure beauty.
7. Looking Tough And Cool At iHeartRadio In 2015
Sometimes, simple is best. Taylor’s short black dress with sparkling sequins that looks like she’s wearing the starry night sky and stiletto heels work excellently for her during her red carpet appearance at the 2015 iHeartRadio event. The swinging 60s banged hairstyle is also a nice touch to cap off her overall look. Here, she gets to showcase her long legs that have mostly been hidden by many a long-skirted dress or form-hugging gown meant to highlight her hourglass figure and model-like thinness. Once again, the pop diva proves that she knows when to dress appropriately for the occasion. The iHeartRadio Music Awards has a more relaxed atmosphere. It doesn’t have the long legacy of something like the almost 90-year-old Academy Awards or the almost 60-year-old Grammy Awards, so something more modern is called for.
6. A Class Act At The Giver Premiere
During the premiere of The Giver, Taylor was seen sporting a subdued red top with long silken pink skirt that oozed sophistication. In the movie, she was cast as the emotionless girl known as Rosemary. She arguably stole the show both in the film and in the premiere. The sci-fi drama film stars Hollywood heavyweights like Jeff Bridges as the titular character, Meryl Streep as the Chief Elder and Katie Holmes as Jonas’s mother. This is Taylor’s most significant Hollywood role since she played the female lead Audrey in The Lorax, the 3D CGI film adaptation of a famous environmental Dr. Seuss book. She has also appeared on Saturday Night Live as the musical guest and second-youngest host (next to Britney Spears) and the murder victim in an episode of CSI: Crime Scene Investigation. She has appeared as one of many cameos in the film Valentine’s Day as well.
5. Making Us Swoon At The Vanity Fair Oscars After Party In 2014
For a girl known for making songs about her breakups and failed relationships, with her album looking more like allusions to her diary, Taylor appears less like the bitter scorned woman that pop culture insists she is on the red carpet and more like the strong, independent woman found in songs like Diana Ross‘ “I Will Survive” and Aretha Franklin‘s “Respect.” She commands prestige and power rather than pity. Nothing says, “Yaaaas, queen!” quite like what Taylor Swift wore to the Vanity Fair Oscars After Party in 2014. It’s like the long formal gown version of her swinging 60s “Starry Night” mini-dress that she wore to the 2015 iHeartRadio Music Awards. The 1950s Veronica Lake tresses is also an appropriate hairdo for this stylish and more glamorous turn of the same theme. Actually, her style is very reminiscent of the Golden Age of Hollywood.
4. Simple But Perfect At iHeartRadio In 2014
Speaking of iHeartRadio, Taylor wore quite the most casual dress in her red carpet catalog at the inaugural iHeartRadio Music Awards. She specifically had a white tube top and a red thigh-high skirt on. When it comes to mini-dresses and mini-skirts, the go-to event for these fashion items as far as Miss Swift is concerned is this millennial age music awards that was founded recently. Just to be clear, even though Taylor reserves her Sunday’s best during formal events like the Grammys and the Oscars, it doesn’t mean she takes iHeartRadio’s special event any less seriously. If anything, fans of Taylor Swift can get to know a less reserved and more fun side of her whenever she graces the red carpet of this awards ceremony. She, after all, loves the fans and is honored to have her music remain relevant among not only music critics but the mainstream audience at large.
3. She Looked Elegant In Gold At The American Music Awards In 2012
The American Music Awards 2012 showcases how consistent Taylor is when it comes to her red carpet fashion. In fact, in an effort to evolve, she ditched her usual long-gown style and settled for a cute mini that she’d later wear to more laid-back events like the iHeartRadio Music Awards or her own movie premieres. She knows how to avoid coming in underdressed or overdressed. At the 2012 AMAs, her brand new look (at the time) helped Miss Swift define a more unfussy and informal red carpet look that helped her become more accessible to her fans. It also helped her get out of the rut of wearing a strapless embellished gold gown that had become her signature back in the 2000s. This time around, she let her proverbial coiffed hair down at the 40th Anniversary of the AMAs. Not coincidentally, her music also began to transform into something more accessible to millennials after she wore something as bold and mature as a form-fitting mini-dress that she hadn’t worn previously before.
2. She Went With A Sparkly Barbie Doll Look At The American Music Awards In 2010
As for the AMAs 2010 two years earlier, Taylor went with the safe bet of her wearing a glamorous mirrored Collete Dinnigan dress. This was the mold that she broke at the AMAs 2012 two years later. This is the red carpet look that Miss Swift was most famous for. It’s a tradition she continues to this day when attending grandfathered events like the Grammys and the Oscars. As discussed earlier, although there will always be a geeky, down-to-earth side of her that gives her music that much-needed relatability to millennial or generation Z girls that allowed her to zoom at the top of the pops time and time again, there’s no mistaking that she has also transformed into an untouchable diva who has realized the full potential of her once-in-a-lifetime talent as well. Jennifer Lopez may insist she’s still Jenny from the Block, but she’s also the most influential Hispanic performer in the United States. In the same regard, even though Taylor Swift is still the music-obsessed kid from Pennsylvania, she’s also one of the leading contemporary recording artists of the millennial generation. Sometimes, when you have it, you got to flaunt it.
1. She Wowed The World At The Oscars In 2016
At the 2016 Oscars or the 88th Academy Awards, the chart-topping country singer turned pop icon wore a revealing black dress with a truly plunging neckline that reaches all the way to her midriff, exposing her chest and her abdomen. The first female artist to succeed herself with back-to-back hits “Shake It Off” and “Blank Space” also has quite the gazelle-like model look popularized by supermodels like Kate Moss.
As typical of blondes like her, Taylor looks absolutely mesmerizing in her black gown that highlights her golden girl good looks. The seven-time Grammy Awards winner is familiar with winning the gold, but she hasn’t crossed over completely to the world of acting quite yet (voice acting gigs and musical guest roles aside), so no Oscars for her. It’s the same world of acting that Jennifer Lopez was able to successfully enter but fellow pop diva Mariah Carey couldn’t. Who knows if Taylor has what it takes to succeed in the world of acting.
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