Wino Forever! A Look Back at the Screen Queen’s Most Iconic Looks

1990: Winona Ryder with then-fiancé Johnny Depp

1991: Winona masters the art of casual cool in light wash mom jeans, a leather jacket and a vintage Tom Waits shirt.

1994: Winona wearing a vintage flapper dress at a party in Manhattan.

1994: This gallery would not be complete without the floral grunge dress Winona wore as Leilana Pierce in ‘Reality Bites.’

1994: Remember when Winona was dating Dave Pirner? Us neither. Anyways, here she is during that era wearing a green velvet maxi dress to the premiere of ‘Reality Bites.’

1996: This is the first and only time Winona will ever be spotted wearing a pattern.

1996: Hair in vintage pin-curls for the 68th Academy Awards.

1996: Looking adorable in the vampire-y neckline alongside the also-very-cute Claire Danes

1997: Winona in a punchy pink gown for a Martin Scorsese-themed event in Los Angeles.

1997: Winona wears an elegant vintage-inspired lace dress to the 1997 Vanity Fair Oscars afterparty.

1998: Whoever made this coat needs to reissue it immediately. (Though knowing Winona, it’s probably vintage.)

1998: Another gorgeous and slightly risque lace look.

1998: Late ’90s Winona wore a lot of leather. (And clogs!)

1998: Wearing a super-casual outfit in anticipation of the uber-casual trend of the early 2000s to come.

1999: Winona attends the premiere of ‘The Talented Mr. Ripley’ with a man wearing diagonal striped pants.

1999: More leather and lace for the premiere of ‘Girl, Interrupted.’

2000: Winona wearing a hair barrette(!) the premiere of ‘Traffic.’

2000: Winona embodying early 2000s hipster cool.

2000: Winona posing with makeup artist Kevyn Aucoin (middle) at the 57th Golden Globe Awards.

2000: Winona and Matt Damon were a seriously cute couple.

2001: Winona pals around on the red carpet with Courtney Love

2002: The eggplant coat and black headband Winona chose for her court appearance when she was found guilty of shoplifting is forever seared into our collective memories.

2004: Winona channeling a Grecian goddess at event in New York.

2005: A posh and pretty A-line skirt paired with a chic blazer for a luncheon benefit in Los Angeles.

2006: Winona wears her signature, a strappy black dress, to the premiere of A Scanner Darkly.

2007: Is Winona really wearing a baseball cap to a film premiere?! The mid-2000s truly were a different time.

2008: Switching it up by wearing pink pumps with her usual all-black attire.

2009: Pretty as a picture at the ‘Star Trek’ film premiere.

2010: This ’50s-inspired poofy ballerina dress is just vintage enough to be classic Winona.

2011: Wearing a confectionary dress with a tiny black purse to the Screen Actors Guild Awards.

2012: Wearing a polka-dot suit to the Marni x H&M launch in Los Angeles. How much do you want to bet she wore this outfit literally once?

2013: A perfectly-fitted black sheath dress by Cushnie et Ochs for the premiere of ‘Homefront.’

2013: Winona still looking incredible in red lipstick.

Undated: Winona attends a collection launch party for the brand Loomstate.

2016: Winona apparently still owns the Tom Waits she paired with mom jeans in the ’90s.

2017: Strapless? Check. A-line? Check. Winona in Viktor & Rolf for the 74th Annual Golden Globes.