Great Outfits in Fashion History: Winona Ryder's Iconic Courtroom Look

The actor stood trial in 2002 looking chic and demure, earning herself a campaign with one of the designers whose merchandise she stole.

There are perfectly good celebrity style moments, and then there are the looks that really stick with you, the ones you try desperately to recreate at home. In ‘Great Outfits in Fashion History,’ Fashionista editors are revisiting their all-time favorite lewks.

Winona Ryder has never been one to disappoint on the red carpet, consistently looking inimitably cool whether in jeans and a motorcycle jacket or an elegant, re-worn strapless grown. She’s always come across as one of those celebrities with authentically good style. In fact, she loves fashion so much that she stole $5,500 worth from Saks Fifth Avenue in Beverly Hills in December of 2001.

The case went to trial and throughout the fall of 2002, Ryder made several court appearances in outfits so noteworthy they prompted a Robin Givhan Washinton Post think piece. “She may be a shoplifter, but she has impeccable taste,” Givhan quips in the article.

Over the course of the trial there were several looks, but they all fit neatly within a ’50s-inspired aesthetic that was feminine without being too girly, elevated without being flashy. Knee-length, A-line silhouettes, Mary Jane heels and thick headbands were all key. Highlights included an eggplant-hued coat dress paired with a Fendi bag (top) and a Marc Jacobs sweater dress with a trompe l’oeil collar (below).

Having also stolen a piece by Jacobs, Ryder was clearly a fan of the brand. Jacobs himself evidently caught wind of that and went on to cast her in his Spring 2003 ad campaign — a pretty good consolation prize for Ryder, who was found guilty of grand theft and felony vandalism.

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While I personally have yet to be put on trial, I know I’ll have these looks as a reference for what to wear if it ever happens. If you, too, want to start preparing for a hypothetical court appearance — or any other occasion that calls for a chic-yet-responsible vibe, shop the gallery below.