2014, Taylor Swift
In the realm of VMAs fashion, a short romper might not be the most scandalous choice… But when it came to Taylor Swift, the unexpectedness of her daring romper made it a head-turning moment. After all, Taylor had made a name for herself with her poignant breakup songs and “cottage-core” French braids, not with leggy looks.

The singer, known for her penchant for classic and safe red carpet choices, decided to surprise everyone at the 2014 VMAs with this edgier ensemble, showcasing a new facet of her style persona. It was a fashion moment that left fans both pleasantly surprised and eagerly anticipating what Taylor Swift would bring to the red carpet in the future.