Here's How Taylor Swift's Style Changed When She Dated A Member Of The Kennedy Family

Taylor Swift's stunning transformation from the princess of country music to a multi-genre pop icon has been nearly two decades in the making. Throughout each of Swift's iconic eras, she has tested the limits of her songwriting skills and the public's approval. While her styles — both in fashion and music — have changed over the course of her career, her ability to capture whirlwind romances in her music never waned.

Conor Kennedy — rumored to have been the inspiration behind the "Red" track "Begin Again" — might be one of Swift's exes that you have forgotten about (via Us Weekly). Swift's past relationships have received mountains of media attention over the course of her impressive career, especially the short-lived summer she spent linked with Kennedy in 2012. 

And while their relationship came and went, the Kennedy family had a lasting impact on her personal style, which helped the country girl transform into a chic young woman with some of the industry's most memorable looks.

Taylor Swift reportedly became close to the Kennedy family after Rory Kennedy — the daughter of Ethel and the late Robert F. Kennedy — asked Swift's teams for concert tickets in the summer of 2011, according to InStyle. After meeting Rory, Swift asked if she could be introduced to the matriarch of the family; her friendship with the family blossomed from there. It's even rumored that the "Red" track "Starlight" is about Ethel's star-crossed romance with her husband.

When Swift met Rory, she was already maturing in her style. The star traded cowboy boots for black leather boots during the "Speak Now" tour while still rocking her iconic curls (via Billboard). Her streetwear evolved as well, according to Footwear News. Rather than wearing flannel shirts or school-girl pleated skirts, Swift opted for a timeless sundress, cardigan, and kitten heels for an outing in early 2011. 

Her style would evolve even more after dating one of the Kennedys.

Taylor Swift began dating Conor Kennedy in the summer of 2012, according to Elle. "Conor put his arm around Taylor and they kissed behind the boat shed," a source told Us Weekly about one seemingly romantic July day they spent together.

The summer of 2012 marked a turning point for Swift's fashion evolution. That was the year she premiered her bangs and straight hair. Alongside Kennedy and his family, the "Style" singer kept her style preppy — even her swimwear (via People). One red polka dot high-waisted bikini she rocked perfectly matched her lipstick while she waded through the water, showing that the singer was never going to sacrifice her looks.

While her friendship with the Kennedys was seemingly taking off, it's worth pointing out that she might not have gotten along with ever family member. J. Randy Taraborrelli wrote that Patrick Kennedy said "the girl in the bathing suit walking down the path to the docks was Taylor Swift, who was then dating my nephew and probably already composing the song about their breakup," according to InStyle.

Before dating Conor Kennedy, Taylor Swift still donned her infamous blonde curls, cowboy boots, and gowns fit for the princess of country music. While their relationship was short, Swift's style was forever changed. Leading up to the "Red" era, she began straightening her hair and experimenting with her fashion. Sundresses, shades, scarves, and ballet flats became a go-to combination. She was spotted often wearing high-waisted shorts and tees alongside Kennedy. Swift traded her country upbringing and seemed to be referencing Jackie Kennedy with her new preppy and elegant looks (via the Daily Beast).

Even after the couple parted ways, Swift's style continued to evolve. Her street style, according to Elle Canada, morphed into 1950s-inspired silhouettes. That fashion inspiration bled into the "Red" tour outfits, too. The show featured high-waisted shorts, a polka dot skirt, and a ballerina-esque dress. During the "Red" era, Swift matured in her style, music, and attitude. 

"Musically and lyrically, Red resembled a heartbroken person," Swift said in 2021 (per NME). "It was all over the place, a fractured mosaic of feelings that somehow all fit together in the end. Happy, free, confused, lonely, devastated, euphoric, wild, and tortured by memories past." Those memories — and Swift's style — are still iconic a decade later.