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.