How Winona Ryder’s Courtroom Style Became an Iconic Marc Jacobs Ad
The early 2000s had no shortage of scandals, but few were as strangely captivating as Winona Ryder’s shoplifting case. In 2001, she was caught taking approximately $5,560 worth of designer goods from Saks Fifth Avenue, including a $750 Marc Jacobs cashmere sweater.
The story caught headlines and turned the indie darling of Edward Scissorhands and The Crucible into the unexpected star of a courtroom drama. What made this crime saga unforgettable was how Winona managed to turn her trial into one of fashion’s most talked-about moments.
The Golden Globe-winner’s looks during the trial were soft and almost old-fashioned. Most memorable was a burgundy Marc Jacobs dress with a contrasting collar from his fall 2001 collection. The Washington Post described her look as “smart but conservative,” “chic, refined, demure and guilty.”
A Trial That Became a Spectacle

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The six-day trial was treated like must-see television. The Los Angeles District Attorney’s office, led by Stephen Cooley, pressed forward with felony charges.
For many, it seemed absurd that a shoplifting charge involving designer pieces, some valued at hundreds of dollars, would drag on for so long. Still, the drama played out in full view, and Winona’s carefully curated courtroom image became one of the most talked-about aspects of the case. The public noticed, but so did Marc Jacobs.
While her career hit a major pause after the guilty verdict, her style choices caught the designer’s attention. He later cast her in his 2003 campaign.
The Defendant That Became a Muse
By 2003, Marc Jacobs invited her to front his spring-summer campaign, shot by Juergen Teller. The images had a raw, moody energy that played into her vulnerability and Jacobs’ knack for mixing glam with grit. It was a bold casting choice, but one that worked perfectly.
She went on to appear in campaigns for Marc Jacobs Beauty in 2015 and most recently posed with the J Marc Shoulder Bag. Marc Jacobs celebrated her appearance, and his loyalty stood out in an industry quick to abandon stars at the first hint of scandal. For him, Winona was never defined by a courtroom but by the unique strength that he believed reflected his brand.
Why It Still Matters
More than 20 years later, the trial remains a topic of discussion. Nostalgia-driven Instagram pages, such as @90sanxiety and @cabmate, continue to share her looks, while Reddit threads spark debates about whether the punishment fits the crime. Many point out that she faced a harsher cultural backlash for shoplifting than other stars have for far more serious allegations.