Ashley Olsen
To be candid, we're utterly fascinated by the Olsen twins. This fascination may stem from the fact that they were ubiquitous in the 1990s and later evolved into grunge fashion icons in the 2000s. Ashley leaned toward a slightly more classic aesthetic when expressing their styles.
The twins have since retired from acting (understandably so) but remain active in fashion. Ashley now sports a more mature rendition of her classy grunge look, often complemented by oversized sunglasses.