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So Many Men, So Many Looks: How Taylor Swift’s Style Changes With Each New Boyfriend

So Many Men, So Many Looks: How Taylor Swift’s Style Changes With Each New Boyfriend

Posted in Celebrity Style By
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    Harry Styles: Fresh off her relationship with Conor Kennedy, Swift started dating One Direction's resident bad boy Harry Styles. The British singer is known for his unkempt hair and varsity jackets, and Swift has been channeling his laid-back style out and about in New York City

    Since they began dating a few weeks ago, she's transitioned into a fashionable hipster and less like the prim New England lady she was just weeks before. Click through the gallery to witness Swift's style evolution as she dates different men. 

    Photo: Stylecaster Pictures /
  • 2012 iHeartRadio Music Festival - Day 2 - Backstage

    Conor Kennedy: When Swift began dating 18-year-old Kennedy offspring Conor Kennedy in July, many were unsure as to how the country-pop star would rise to the occasion. After all, the Kennedys are essentially America's royal family. Naturally, the duo got serious quickly, taking cross-country private jets to Kennedy's compound in Hyannis Port. Swift immediately took to the role of Camelot girlfriend, and also to its style: She was rarely seen without her Cape Cod-chic breton stripes, tiny polka-dots, demure flats, wayfarers and other "Jackie O does the beach" looks. 

    Photo: Getty Images / Isaac Brekken
  • 2012 iHeartRadio Music Festival - Day 2 - Show

    Even when performing, Swift incorporated the classic style she rocked on the beach with Conor (polka dots, stripes and high-waisted everything).

    Photo: Getty Images / Christopher Polk
  • 2012 MTV Video Music Awards - Show

    See? She even wears preppy stripes while performing at the VMAs.  

    Photo: Getty Images / Christopher Polk
  • Minnesota Wild v Los Angeles Kings

    Chord Overstreet: Although Taylor and the "Glee" star never confirmed their relationship, they were rumored to have had a fling in early 2011. Since Chord can be classified as a stereotypical jock type, it makes sense that their first public appearance was at an L.A. hockey game—and Swift dressed the part in casual courtside gear. 

    Photo: Getty Images / Jeff Gross
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    Jake Gyllenhaal: While all of Swift's boyfriends have had dramatic effects on her, Gyllenhaal seems to have had the most influence. On her latest album Red, Swift directly addresses him and the time they spent together (see the above photograph taken in Brooklyn, circa 2010). During their courtship, Swift played the part of a Williamsburg hipster. From skinny jeans to unkempt hair, Swift avoided the red carpet and stuck to Prospect Park West. The glamazon that had evolved was quickly silenced by her low-key boyfriend—until he left her high and dry. 

    Photo: Stylecaster Pictures /
  • Roberto Cavalli - Front Row: Milan Fashion Week Womenswear S/S 2011

    Single: Between Mayer and Gyllenhaal, Swift was single (at least for a few months) and she set out to prove that she'd grown up. The singer showed off her fashion prowess at Milan Fashion Week in September 2010 and rocked an empowering red lip, which has because a Swift staple both on and off the red carpet. 

    Photo: Getty Images / Vittorio Zunino Celotto
  • VEVO Launches Premiere Destination for Premium Music Video - Inside

    John Mayer: One of Swift's most high-profile companions has been 35-year-old singer John Mayer. Despite a serious age gap, they dated for four months in 2009. Swift left the relationship incredibly bitter, which she documented in a less-than-subtle song called "Dear John" on her 2010 album Speak Now. Since she had a lot to compete with (Mayer has dated everyone from Jennifer Aniston to Jessica Simpson), it seemed she stepped up the sexiness (note the cleavage and embellished v-neck dress above).

    Photo: Getty Images / Dimitrios Kambouris
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    While performing with Mayer a few months earlier, she opted to wear a sexy dramatic sequined look, which was her way of telling us that the teenage country princess had left the building. 

    Photo: Stylecaster Pictures /
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    Joe Jonas: Swift had a four-month relationship with singer Joe Jonas back in 2008, and she certainly dressed the part. Jonas has a famously squeaky-clean image—but also has a flair for flamboyant stage attire. She matched his passion here, experimenting with trendy but wholesome looks.

    Photo: Stylecaster Pictures /
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    During her time with Jonas, Swift was an all-American prom queen, and that's how her brand was built. My, she's come a long way. 

    Photo: Stylecaster Pictures /

It’s no secret that Taylor Swift has built her wildly successful career by being honest with her listeners and not holding anything back. It’s also no secret that the 22-year-old is a fan of penning an endless array of confessional tracks where she spills dirt on some of her famous ex-boyfriends (a list which includes John Mayer and Jake Gyllenhaal).

Despite the slew of men she’s had in her relatively short life (and the seemingly rapid frequency at which they appear), she somehow manages to maintain an unbreakable good-girl image (a major feat in Hollywood, we say). One thing that always does seem to change according to the men she dates: Her style.

We decided to investigate this phenomenon and trace Swift’s style evolution as it relates to the many men she’s been involved with.

Click through the slideshow above to see how Taylor’s fashion changes based on who she’s dating, and let us know—which Tay Swift phase was your fave? 

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