1990, MC Hammer
The 1980s and early ’90s were undeniably a treasure trove of memorable fashion moments, both good and, well, not-so-good. Among the era’s more questionable trends was the rise of harem pants, a style famously championed by none other than the rapper and dancer extraordinaire MC Hammer.

However, it’s the 1990 VMAs that left us with a particularly unforgettable fashion memory, as the iconic rapper graced the stage in a pair of metallic harem pants that defied gravity, paired with a jacket that seemed to have misplaced significant portions of its fabric.