Celebs Who Showed Up To Court In Inappropriate Outfits

Most celebrities employ a slew of people who advise them on what to do — and what not to do — in situations related to both business and personal matters. When it comes to a big court case, it's not uncommon for a star to hire a team of lawyers and possibly even consultants. Given the psychology behind courtroom style, it's no surprise that many celebs heading to court pay a great deal of attention to the image they cultivate via their outfits and grooming choices.

Winona Ryder's 2001 trial on charges of theft, commercial burglary, and vandalism garnered a lot of attention because of her sartorial choices in court. She looked so stylish in the courtroom that she even landed a Marc Jacobs campaign — after being on trial for stealing Marc Jacobs clothing (and more) from a Saks Fifth Avenue store. Even untraditional celebs like Anna Delvey and Elizabeth Holmes now carefully consider their courtroom style based on the impression it can make on jurors, judges, and the public. However, not all of their choices have been successful.

For the Oscars after-parties, the Met Gala, or even just a family party, Kim Kardashian has worn some extremely expensive outfits — and her court ensembles are no different. But for a robbery case in court, her sartorial choices have struck people as especially peculiar. The case is not just about any robbery but Kardashian's own horrific ordeal in which thieves stole millions of dollars worth of diamonds from her Paris hotel room in 2016. The suspects posed as police officers to gain access to the room, after which they gagged and bound the star before scooping up the jewels. Given all of this, people expected Kardashian to arrive at court in low-key outfits without much glitz and glam. Instead, she decked herself in designer clothing and millions of dollars of diamonds — a giant middle finger to her assailants.

While the burglary occurred during Paris Fashion Week in 2016, the trial didn't occur until 2025. Kardashian flew to Paris to testify and walked into court in a stunning John Galliano gown with dramatic shoulders and a peplum waistline. The black dress was accented by black Saint Laurent heels, black sunglasses, and diamonds — $7 million dollars worth of diamonds, to be precise. This included an $8,100 Briony Raymond ear cuff, as well as a massive Samer Halimeh New York necklace, earrings, rings, and an anklet. Though some experts felt Kardashian's display of wealth could backfire, the court convicted eight of the accused conspirators despite the excessively flashy display.

By now, we all know many of the tragic details about Amanda Bynes' life, including the mental health struggles and legal problems that led to the downfall of her thriving career. The "All That" star seamlessly transitioned from TV to film around 2002, and everyone was excited to see what she would do next after filming the progressive cult classic "She's the Man" and "Hairspray." But not long after Bynes' final acting role (in 2010's "Easy A"), her off-screen troubles began to overshadow her work. In addition to her legal issues, Bynes' shocking social media activity and startling wigs made her a tabloid staple.

Bynes was first arrested for a DUI in April 2012 — in which she infamously tweeted at President Obama for help months later before her plea. However, she was charged with two misdemeanor hit-and-run counts that September. In May 2013, she was once again jailed after throwing a bong out the window of her 36th-floor New York apartment and charged with marijuana possession, reckless endangerment, and evidence tampering. She subsequently arrived in court in black sweats, which she accessorized with a matted blonde wig that largely covered her eyes.

In July 2013, Bynes decided to wear a slightly less awful but still very inappropriate blue wig to court. She paired this with giant sunglasses, black sweatpants, and a casual tank top resembling a jersey. That same month, the star was placed on a 5150 psychiatric hold after lighting a fire in a driveway.

Michael Jackson was a one-of-a-kind talent, but he was also a one-of-a-kind character. For all of his eccentricity, however, he was not known to be underdressed. In fact, the star often looked like he was ready for the stage, even when casually roaming the streets. That is the vibe Jackson brought to court when he first started attending his trial for child molestation in 2005. Reporters and the public alike were puzzled by his choices that first week, as his outfits included things like flashy waistcoats, brocaded vests, colored armbands, and British regimental medals.

Next came a single day when M.J. showed up looking somewhat normal — or as normal as he got — dressed in black trousers, a white shirt, and a red tie, which he accessorized with a stylish pair of glasses. But the appropriate courthouse look was a one-off, and what came next was far more surprising than waistcoat jewelry.

Jackson did not originally show up on March 11 because he claimed to be in the hospital with a back issue. After the judge gave him an hour to arrive in court, the King of Pop rolled in wearing a black blazer over a white T-shirt — and a baggy pair of blue pajama pants with slippers. "I told Michael to come to court the way he was dressed," Jackson's lawyer Tom Mesereau said on "Time Presents: Celebrities on Trial" (via Entertainment Weekly). "Don't risk losing bail and risk being in jail throughout the rest of the trial."

Like with Michael Jackson, no one expected Cardi B to arrive in court totally subdued, sartorially speaking. That said, we were not predicting that the rapper would show up to face her assault charges dressed in fashions so over the top that they would better fit on a red carpet than in a courthouse. The most notable of these outfits was a black-and-white ensemble that made the star look like some sort of bird, thanks to a bold feather coat with a long train and a massive fur hood (all in black). Black trousers, a white shirt, a black tie, and black stilettos made up the rest of the outfit, which the rapper wore in 2019.

For every person who thought it was a major fashion moment, there was another who felt she was downplaying the seriousness of the charges by turning her court arrival into a fashion show. There were, of course, other outfits that some deemed inappropriate for someone facing four years in jail, including a hot pink pantsuit with matching pink heels and a navy suit with no shirt underneath and major cleavage.

"Cardi treats her trips to the courthouse like a runway show," opposing counsel Joseph Tacopina said to the New York Post. "Here's a woman who got indicted by a grand jury with felony charges and appears to only be concerned about what she's wearing ... There's going to be a 'Come to Jesus' moment with her because it's not consistent with someone who's taking this seriously."

Harvey Weinstein is nothing if not calculating, and the disgraced Hollywood producer tried to use his manipulative tactics on the court when he arrived for his arraignment in May 2018. Actually, he started before that — walking into a police station to turn himself in while wearing a crinkled V-neck sweater in a periwinkle hue that W magazine noted evoked innocence (and carrying a handful of books like a college undergrad headed to chemistry 101). He wore the same outfit later that day when he headed to court, including a black blazer and a white button-down shirt with a missing button at the collar.

Nobody was buying the act, but Weinstein stuck with his strategy. "[W]hen Weinstein arrived for the opening of his highly anticipated trial, he'd assembled a meticulous wardrobe for a specific character: a weakened man. An ailing man, a man to pity," wrote Monica Hesse in the Washington Post. "Those dozens of stories of Weinstein allegedly raping women: How could such a frail man do such a violent thing?" Not only did Weinstein dress like a schlub for this appearance, but he also pulled out a walker with neon tennis balls on the bottom. Meanwhile, sources have said he used the walker only for public appearances and not in his everyday life. Weinstein has been to court many times since, and he continues to look unkempt. On March 12, 2025, for example, he wore a crooked tie and a stained button-down shirt under his ill-fitting suit.

Courtney Love had a memorable run as a fashionista around the time she appeared in "The People vs. Larry Flynt," but aside from that period, she has not been known for looking polished and put together. So, finding the oft-disheveled star on our list should not come as a surprise considering how often she has seen the inside of a courtroom. While her hair has been a mess pretty much every time, Love has not always disappointed with her outfits. She looked perfectly appropriate when she arrived to face assault charges on November 18, 2005, for example. She looked similarly fine — albeit frumpy — when arriving for her arraignment just over a year prior.

But Love has made some incredibly questionable courthouse fashion choices as well, including wearing a black bucket hat that totally covered her eyes to a pretrial hearing on December 11, 2003. Love removed the hat to reveal a messy head of hair, shocking no one. But the biggest issue was the outfit itself, as she wore wrinkled pants and a cropped pink blazer over a midriff-baring shirt with a tie in the front. The purse and belt were awful, too, but not necessarily inappropriate.

Another particularly questionable outfit was the one Love wore on April 15, 2004, when she arrived for a preliminary hearing regarding felony drug charges. Though she arrived with a coat, Love removed it to reveal a black strapless dress, which she had to keep hiking up due to how low it sat.

Pamela Anderson and Courtney Love are known to be good friends, so she is the perfect person to follow the Hole singer on this list. In 2024, Pamela Anderson famously embraced a more natural aesthetic, going makeup free and adopting a more demure clothing style than the kind for which she had been known. But this all came two decades after Anderson was in court battling for custody of her children, and she probably could have used a little bit of help getting dressed back then as well. Though Anderson's sex appeal is what made her a star in the first place, she had not yet learned when to dial it down. Like in family court, for example, where all elements of one's impressions on the judge matter.

Anderson filed for divorce from her first husband Tommy Lee, for the second time, in February 1998. This came two days after Lee was arrested in a domestic dispute, and only hours after he was charged with spousal and child abuse. The couple later got back together, then broke up again, which was a cycle they would repeat numerous times. In the middle of this particular cycle, in 2002, the stars entered into a bitter custody dispute that took them to court. It was Anderson's August 19 court appearance that many criticized as being too revealing for a courtroom. The "Baywatch" star wore a neon pink, yellow, and green dress with spaghetti straps and a plunging neckline that left very little to the imagination.