Flavor Flav, 1990
We understand dressing for comfort, but rapper-turned-reality-star Flavor Flav took casual wear to the next level with his 1990 VMAs outfit. Flav wore his finest pajamas and slippers (!) to the event. If that wasn’t bizarre enough, he accessorized with a hot pink batman mask and his signature oversized clock around his neck.
Getty Images Photo by Jeff Kravitz
Perhaps he was planning on sneaking in a few naps during the show? Either way, we applaud his dedication to dressing comfortably, even if it means looking silly.
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Eve, 2000
We're not exactly sure, but somehow Eve managed to find a fur shawl that matched her hair color exactly. While most of her red-accented outfit blends into the red carpet, no one could miss her bright metallic gold dress.
Getty Images Photo by Ron Galella
The asymmetrical dress with the thick jeweled choker is surprisingly back in style today. With her signature short red hair and undeniable confidence, we’re sure no one was asking, “Who’s That Girl” when she stepped onto the red carpet!