However, finally, Vogue's notoriously private editor-in-chief is revealing why she has remained committed decades to the full fringe.
"You're about to go on a magnificent journey," she addressed to her younger self in a public service announcement on Late Night with Seth Meyers clad in a Hillary '16 t-shirt. "Before you do, here is a bit of advice."
"Don't get a tattoo of a dot on your forehead, because then you'll have to wear bangs for the rest of your life," the 66-year-old teased, poking fun at her iconic look.
While we highly doubt an esteemed fashionista like Wintour would ever even contemplate such a tattoo, we appreciate the joke nonetheless.
Meanwhile, Lena Dunham was her own punchline while joking about a certain career milestone.
"One TV show about four friends will change your life forever," she began in an additional message to her younger self. "That show is called Teenage Mutant Ninja Turtles." Nice one, Lena.
"Basically, you're just going to rip it off wholesale. Hannah, Marnie, Jessa and Shosh are pretty much just Donatello, Rafael, Leonardo and Michelangelo, but with vaginas," she continued. "So, in a couple years when you're in a pitch meeting with HBO, you just blurt out Teenage Mutant Ninja Turtles, but the turtles are girls, they'll give you a blank check faster than you can say 'Cowabunga dude!'"
Lastly, Cyndi Lauper took center stage to tell her younger self about the days when girls aren't just worried about having fun.
"Right now, you probably think that girls just want to have fun, but as a grown up, life isn't all about just having fun," she warned. "Girls gotta have a solid investment strategy. Girls gotta build a diversified portfolio."
Even a free spirit like Lauper understands the boring benefits of a Roth IRA and 401K.
"You know, what's really fun—is peace of mind and financial security," she concluded. If you say so, Cyndi.
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