2006, Fergie

During the early 2000s, Fergie was on a mission to carve out a solo music career that would distinguish her from her role as a member of the Black Eyed Peas. However, her choice of attire during this era left many wondering if she was making the right statement. But this particular school-girl-inspired ensemble didn’t do the trick…

With its peculiar blend of old-fashioned businessman elements fused with go-go dancer vibes, Fergie’s outfit left many baffled by its eccentricity. Unfortunately, this perplexing style seemed to become a recurring theme for her during that period, culminating in a rather provocative take on a Girl Scouts uniform in her “Fergalicious” music video.