When Swift met Rory, she was already maturing in her style.
Her streetwear evolved as well, according toFootwear News.
Her style would evolve even more after dating one of the Kennedys.

The summer of 2012 marked a turning point for Swift’s fashion evolution.
That was the year she premiered her bangs and straight hair.
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.

Even after the couple parted ways, Swift’s style continued to evolve.
Her street style, according toElle 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 (perNME).
Those memories and Swift’s style are still iconic a decade later.