Who: River Phoenix and Martha Plimpton
When: March 29th, 1989
Where: The 61st Annual Academy Awards, Los Angeles
Why: An essential part of being cool has always been not caring about being cool (or at least really convincingly looking like you don't care). And at the Oscars in 1989, River Phoenix (RIP) and Martha Plimpton had that down. They were pre-grunge style gods, paving the way for a decade of glorious no-fucks-given style. Seriously, their "je ne sais quoi" (French for dope) here is the stuff designers and trendsetters have been trying to distill for the past 20 odd years. We'd bet good money Hedi Slimane has this photo pinned to a wall somewhere in his studio.
Let's take a minute to unpack and appreciate what's happening here. The duo turned up to the fancy affair dressed like aristocratic hippie royalty straight out of a black-tie gala in Laurel Canyon. Amazingly, though, it's 27 years later and nothing about this photo—aside from the ladies behind them—looks that dated. (We could see Robert Pattison and FKA Twigs dressed exactly like this in 2016.) And it bears mentioning, the duo showed up in dress code-appropriate gear, not some showboating sartorial assertion of their outsider-ness. But actual clothing aside, what made these two so incredible was their endless source of swagger. They were wearing their fancy threads, not being worn by them. The point is, while you may not be headed to the Oscars any time soon, or even own a tux, if you can harness the same attitude that Phoenix and Plimpton have in this photo you'll look equally killer in anything you wear—we promise.