She started as a teen country singer with hits like “Tim McGraw” and “Teardrops On My Guitar,” but Taylor Swift has grown into one of music’s most prominent powerhouses. From seamlessly crossing over to the pop charts to living in New York City, fans have seen the star through many eras — and there are surely many more to come.

Over the years, Swift’s style has inevitably evolved along the way. While the singer gravitated towards romantic ball gowns and feminine silhouettes for her early red carpet moments, she’s stepped out of the box more recently with tailored suits and menswear-inspired looks. And just like with her music, Swift is bound to continue to surprise us with her style, whether she’s attending an awards show or strolling around Tribeca.

Keep reading for a look back at some of Taylor Swift‘s best fashion moments.

Taylor Swift at the CMAs in 2006

Shortly after releasing her very first single, “Tim McGraw,” Swift made her CMAs debut in a black, floor-length Elvira gown with black opera gloves. Her signature curls were on full display as well as a dramatic, smoky makeup look.

Taylor Swift at the CMAs in 2007

Swift seemingly channeled Belle’s iconic yellow dress from Beauty and the Beast with her 2007 CMAs look. The brilliant gold gown featured a beaded bodice and satin skirt, and the star’s blonde curls were pulled back and swept over one shoulder. Rather than go for matching jewelry, Swift accessorized with long silver earrings.

Taylor Swift at the 50th Annual Grammy Awards in 2008

For her very first Grammys, Swift embodied her newfound role as music’s girl next door in this strapless lavender dress with beaded detailing on the skirt. She didn’t take home any awards that night (she was nominated for Best New Artist, which Adele won), but the appearance was certainly a memorable start to her journey as a style icon.

Taylor Swift at the CMAs in 2008