Fergie, 2006
In the early 2000s, Fergie was trying to establish a music career outside of being a member of the Black Eyed Peas. That said, this school-girl-inspired outfit was definitely not the outfit to show us she was a serious solo artist.
Getty Images Photo by Jason Merritt
We can’t be the only ones confused by her old-fashioned businessman meets go-go dancer look. Unfortunately, Fergie seemed to stick to different versions of this look throughout that time, including wearing a provocative version of a Girls Scouts uniform in her “Fergalicious” music video.
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Big Boi and Andre 3000, 2001
Outkast members Big Boi and Andre 3000 usually have an effortless cool that makes us look past their rather questionable wardrobe choices. In 2001, however, we couldn’t look away from their cartoonish couture. Looking at their outfits, we were left with many questions.
Getty Images Photo by Theo Wargo
Why was Big Boi wearing pants made from thick pink fur, and what was up with Andre 3000’s orange overall onesie? The green fedora and thick, leather armpiece instantly bring us back to the terrible trends of the early 2000s… ugh.