Flavor Flav, 1990

We’re all for dressing comfortably, but rapper and reality star Flavor Flav elevated casual attire to an unprecedented standard at the 1990 VMAs. Flav donned what looked like his coziest pajamas and slippers for the occasion. And in an unusual twist, he added a hot pink Batman mask and his iconic oversized clock necklace to his ensemble.

Maybe he intended to catch some Zs during the ceremony? Regardless, we give him props for his commitment to comfort, even if it verges on the whimsical.