These Throwback Photos of Winona Ryder Are the Ultimate Beauty Inspiration

Updated 09/23/16

Our unbridled obsession with Stranger Things may have rekindled it, but our love for all things Winona Ryder has run deep for decades. From a beauty standpoint specifically, we can't look back at the '90s without immediately thinking of the actress's ineffable cool factor: From her trendsetting haircuts to her laissez-faire approach to makeup, her approach seemed effortless, yet it always just worked. Not to mention its timelessness: It's always telling when we sift through photos from many years past, only to realize that every single look would still be totally on point today.

(Bare skin, brushed-up brows, and don't-care hair? Hello, 2016.)

So consider this our visual ode to Ryder's enduring cool, from Heathers to Reality Bites to the binge-watch beyond. Below, find a handful of throwback photos that might just inspire tomorrow morning's look—and at the very least, will have you saying #WinonaForever.

Getty/Terry O'Neill

1989

If you're wondering what the ideal bob looks like, Ryder's post-Heathers hair is it. 

Getty/Jim Smeal

1989

A low-key look, save for a swipe of red lipstick has become something of a default for the actress over the years—in this case, complete with brushed-up brows. Try it yourself by using a clear gel, like Nyx's Control Freak ($6).

Getty/Ron Gaiella

1989

Hiding third-day roots can prove tricky with shorter hair, but Ryder knows that an expertly placed bandana makes for a quick and stylish solution.

Getty/ Nancy R. Schiff

1990

This is how no-makeup makeup is really done, FYI. Get that barely there look with Milk Makeup's Sunshine Skin Tint ($42).

Getty/Joe McNally

1994

Before the Rachel, there was the Lelaina. Ryder's Reality Bites 'do was the cool-girl cut of the '90s.

Getty/Barry King

1996

Who can forget the actress's Old Hollywood moment at the 1996 Academy Awards? Get that glossy sheen yourself with a few spritzes of Tigi's Massive Shine Hairpsray ($13).

Getty/Ron Gaiella

1998

Leave it to Winona to sport not one, but two It cuts of the decade. Her piece-y pixie launched countless copycats in salons across the country.

Which is your favorite look? Sound off in the comments below.

Related Stories