2005, Hilary Duff

Hilary Duff, a fixture on the red carpet since her Disney days when she stole our hearts as “Lizzie McGuire” at the age of 13, has undergone a remarkable style transformation over the years. Her evolution from girlish charm to glamorous sophistication was nowhere more apparent than at the 2005 VMAs.

Hilary Duff radiated like a dream in her dazzling sequined and fringed dress. Adding to the excitement of the night, Duff was in a relationship with Joel Madden from Good Charlotte at the time. This red carpet-appearance marked their first public outing as a couple, and they even had the honor of presenting an award onstage together.