The Most Iconic Trial Style in Pop Culture History: Winona Ryder, A$AP Rocky, More

The court is one of those places (like a religious service or a job interview) where we are generally advised to wear our most presentable clothing, but when celebrities are summoned to the court, their "presentable dress" often dares to be different, making pop culture history. The most iconic trial style moments embody small but effective sartorial rebellion, whether that was A$AP Rocky turning the courtroom into a Saint Laurent runway (including $5,300 jackets) or Winona Ryder wearing Marc Jacobs clothes she allegedly stole to trial.

In 2004, Martha Stewart faced trial, and the media mogul was sentenced to five months in prison and two years probation for conspiracy and obstruction. She clutched a tan Hermès Birkin as she walked into the heavily photographed trial. Sporting a $10,000 handbag while being suspected of insider trading isn't the best look, and that's what makes it unforgettable. Another notable trial style trailblazer is none other than Winona Ryder. The actor was found guilty of shoplifting in 2001, and her ensembles cemented her as a style icon. She even wore what she stole.

The drama and discomfort of a big court case has been a tabloid favorite, going back to the gossip magazine heyday chronicling Lindsay Lohan's courtroom battles to social media frenzy around Gwyneth Paltrow's Deer Valley ski crash case. Trial style is an unmissable part of the pop culture landscape.

Read on to see the most iconic trial style moments in pop culture history.

A$AP Rocky's Trial Style: Saint Laurent Suits

A$AP Rocky was recently acquitted after being charged with two felony counts of assault with a deadly weapon in an altercation with Terell Ephron, known as A$AP Relli. For his court appearances, often with Rihanna at his side, the New York-born rapper almost exclusively sported Saint Laurent looks, from his shiny shoes to trench coats, wool suiting, shirts, and more.

Gwyneth Paltrow's Trial Style: G.Label by Goop

Gwyneth Paltrow went to trial regarding a ski collision in Utah in 2016. Terry Sanderson, a retired optometrist claimed that the actress had recklessly crashed into him and sought compensation from Paltrow for his medical bills following the accident. The court determined that Paltrow was not guilty and did not owe Sanderson. The trial took place in 2023 during the peak of the quiet luxury craze and the actress nailed the look sporting The Row and G.Label by her Goop brand in court.

Cardi B's Trial Style: Fur and Christian Louboutin Heels

Cardi B epitomized trial style in two different court appearances. The rapper wore a white monochrome look with Christian Louboutin heels when she was summoned following a physical altercation in a nightclub in 2018. Her signature style didn't take any breaks in the court room.

Lindsay Lohan's Trial Style: Cheeky Manicure

Lindsay Lohan made several court appearances throughout the late 2000s beginning with a DUI, and she began a long battle with the court regarding her rehabilitation and probation. The actor notoriously struggled with drug and alcohol abuse during this time. Her clothes aren't all that people talked about: At a 2010 court appearance, Lohan's nails were painted with cheeky text. They read "F*ck U."

Paris Hilton's Trial Style: Y2K Fashion in Court

In 2007 Paris Hilton was sentenced to 45 days in jail after violating her probation following being charged for driving under the influence. In 2009, she was sued for failing to promote the film Pledge This, the box office failure in which she starred. In both cases, the heiress brought her notorious Y2K style to the court, minus all the pink.

Naomi Campbell's Trial Style: a Little Black Dress

Naomi Campbell looked refined and statuesque after being summoned to court in 2006 regarding an altercation with her maid. Whatever the supermodel wears tends to get people talking, even when it's more reserved. After all, her sleek tresses and little black dress in the early aughts still caught the public's eye.

Martha Stewart's Trial Style: an Hermès Birkin

Martha Stewart was the subject of a highly publicized trial in 2004 after being accused of insider trading and charged with conspiracy and obstruction. This resulted in the media mogul spending five months in prison. Though at the trial, her looks sparked buzz. What was she clutching in court? An Hermès Birkin bag. 

Winona Ryder's Trial Style: Marc Jacobs

In 2001, Winona Ryder was caught shoplifting thousands of dollars' worth of goods from Saks Fifth Avenue, including Marc Jacobs garments. At her trial, she exhibited her good sartorial taste. After being fined and put on three years probation, the actor stepped out of the limelight, though she recently appeared in the 2024 film Beetlejuice Beetlejuice, the sequel to the iconic 1988 film in which also she starred.

Jackie Kennedy Onassis's Trial Style: Jackets, Wool Coats

In 1972 former First Lady, Jackie Onassis sued New York paparazzi photographer Ron Gallela for constant public harassment. She brought her refined taste to her dress in court, and her looks, spanning wool coats and elegant button-up jackets, continue to serve as an original guide to trial style.