7 of the most iconic courtroom outfits

We’re putting Gwyneth Paltrow, Winona Ryder, and Cardi B's courthouse looks on trial.

7 PHOTOS

1. Celebrity trials have a strange way of bringing us all together, no matter whose side you’re on. Who doesn’t love to have a little peek behind the curtain of our favorite celebrities’ pristine public personas, a glimpse of the mishaps and bad behavior that make them just a bit more human? You know: shoplifting, cocaine allegations, freak ski accidents. Celebrities, they’re just like us!

Oh, and, of course, there’s also the courthouse fashion. Since Winona Ryder set the standard for trial dressing back in 2002, celebrities have brought their sartorial A-game as much to the courtroom as the carpets. Rather than naked dresses, however, the courthouse demands a more symbolic wardrobe, one that delivers a message to the judge, the jury, and the public. Demure looks that suggest “innocent until proven guilty.” Over-the-top outfits that say, “Are you not entertained?” Luxe basics that scream, ‘I’m too famous to be here’. From Winona’s iconic Marc Jacobs dress to Gwyneth Paltrow’s bore-core, we’re looking back at some of the courtroom’s most iconic outfits of all time.

1. Winona Ryder, 2002

First, we need to give credit where it’s due. It was Winona Ryder who set the standard for 21st-century courtroom fashion during her 2002 shoplifting trial. The year before, Winona was arrested on shoplifting charges and accused of stealing $5,500 worth of designer clothes, including a Gucci dress and Marc Jacobs sweater, from Saks Fifth Avenue. The subsequent trial was a media frenzy… but also somewhat of a fashion show, with Winona’s courtroom outfits garnering just as much scrutiny as the charges themselves. Even fashion critic Robin Givham weighed in on the actress’s courthouse style. (“She may be a shoplifter, but she has impeccable taste.”) So true! To telegraph her supposed innocence, Winona attended her hearings in demure cardigans, sweet Mary Janes, schoolgirl pleats, and what else but this Marc Jacobs dress. She subsequently went on to star in an MJ beauty campaign in 2015 and became the face of their J Marc shoulder bag last year.

2. Lil Kim, 2004

No one’s ever looked cooler in the courtroom. During her 2004 perjury trial, Lil Kim put her own twist on the ubiquitous courthouse pantsuit, taking the stand in chic pinstriped vests, massive waist-cinching belts, and an it-bag or two. 

3. Lindsay Lohan, 2010

Just as it is for the perfect crime, when it comes to courtroom style, the devil’s often in the details. On the final day of her 2010 DUI trial, Lindsay Lohan pulled up to court with a brand new manicure, a pastel pastiche with “fuck u” etched into the middle fingernail. The actress was found guilty and sentenced to 90 days in jail. The following year, LiLo was called to the courts once again, for violating her probation. This time around, likely learning from the aforementioned beauty blunder, the actress took to the courthouse in less offensive attire: pinstriped shirts, pencil dresses, and not an errant fingernail in sight. 

4. Naomi Campbell, 2010

Of course, supermodel Naomi Campbell can serve a look. But she can also serve as a soundbite. And at her 2010 trial, she gave us both. Wearing a prim Azzedine Alaïa twinset (and an evil eye necklace, for good measure), the super took to the podium, telling the defense: “I just want to get this over with and get on with my life. This is a big inconvenience for me.”

5. Nigella Lawson, 2013

Nigella Lawson’s known for her extravagant cooking, bubbly persona, and wardrobe to match. For a 2013 trial of her and her ex-husband’s personal assistants (two sisters named Elisabetta and Francesca), accused, but eventually found not guilty, of making unauthorized payments on work credit cards, the celebrity chef took to the courtroom in a much more sober look that normal: all-black tailoring.

6. Cardi B, 2023

Most celebrity trials are media circuses. And Cardi B knows how to put on a show. Back in 2019, the rapper attended her misdemeanor trial in a show-stopping ostrich cape. Earlier this year, she kicked it up a notch, arriving to court in a sleek turtleneck dress and larger-than-life fur coat. The look was Big Boi meets Basic Instinct — and utterly perfect.

7. Gwyneth Paltrow, 2023

For the last few days, Gwyneth Paltrow’s ‘hit-and-run’ ski trial has had the internet in an ironclad grip. And it’s not hard to see why. The trial had it all: freak ski accidents, wacky attorneys, thwarted wine tastings, Taylor Swift tidbits, and, of course, the outfits! Not since Winona’s iconic 2002 trial has courtroom style stirred up such a fervor — and such takes. Fashion fans compiling “shop the look” threads, adjudging Mountain Valley Spring Water as an accessory. Unlike Winona, however, Gwyneth’s bore-core looks (The Row, Céline, and head-to-toe Prada) signal not her innocence, but her privileged ennui. After all, she’s lost a few days of skiing for this.