The Fashion and Strategy Behind Famous Court Looks

Ending up in court is never at the top of any celebrity’s bucket list, but for one reason or another, many of them seem to wind up there anyway. Whether it’s a DUI charge, assault charge or divorce battle, most celebrities eventually get their day in court. And regardless of whether it’s their fault or not, they always have to dress for the occasion.

Whether you like it or not, what you wear to court can affect the outcome of your trial, regardless of your innocence. The problem is that you can never be sure how a courtroom will perceive you, so even a carefully selected outfit won’t necessarily have a payoff. Wearing the appropriate courtroom attire before a judge is usually the safest bet but sometimes being yourself makes you a little more transparent. At the same time, dressing like yourself when you are trying to show a stage of change is going to have a counter-effect.

We’ve examined some of the most iconic celebrity courtroom looks of all time and the strategy behind them to show you what we’re talking about. Some of these looks really helped win the case, while others did not, but what is clear is how very deliberate each and every look is. Take a gander at these famous court looks!

In the defamation trial between Amber Heard and Johnny Depp, there has never been a clearer indication that we are dealing with actors. Johnny Depp has certainly brought a bit of his charm and humor to the court and showed up dressed to the nines in his three-piece suits.

Attempting to exude an aura of innocence, Depp’s very demeanor is straight-laced. While usually more relaxed with hair down, sleeves rolled up and tattoos exposed, he’s naturally dressed more appropriate for court. But his formal look also helps him look far more restrained to counteract Heard’s claim that he is anything but. Nevertheless, Depp won his case and earned $2 million in damages.

The word “performance” has been brought up on numerous occasions and it seems they both have a performance going on of a sort. Ms. Heard ends up giving her own performance in court as she channels, or perhaps mocks, Johnny Depp, even down to his attire, wearing a dark three-piece suit and trying to look as serious as possible.

Then when it's time to testify, it’s all tears, heightened emotion, pettiness and drama front-in-center. It’s not merely that we are watching two actors that have made this trial so interesting for everyone, it’s the performances from both parties which are clearly less than innocent but in terms of Depp's defamation case, he now has two more million dollars to enjoy.

In 2002, Winona Ryder was convicted of shoplifting $5,560 worth of clothing from Saks from designer brands like Marc Jacobs and Gucci. Despite the bad girl thing she had done, Ryder when for a good girl look during her trial with subdued colors, Midi skirts, schoolgirl jumpers and other chic clothing of that nature.

Attempting to project a look of innocence while also showing off the fact that she doesn’t need to steal designer brands, her most famous look at the time was this black dress with pink inserts that was part of the 2001 Marc Jacobs collection, which to our knowledge, she did not steal. While she didn’t’ get away with stealing, she didn’t spend any jail time. She got three years of probation, community service, and a $10,000 fine.

Martha Stewart was a former model who was able to build an empire designing crafts, cooking and decorating while sharing that with millions of families across the country right on their TV. The nation was shocked when the wholesome TV host was facing potential jail time for insider trading charges.

Martha Stewart didn’t dress like a woman about to serve jail time, however. She dressed in her chic best with a green pashmina, leather boots and designer handbag, just as we’d expect her to look. Maintaining her composure worked to her advantage because she didn’t get convicted of insider trading, but he did get convicted of conspiracy to obstruct, obstruction of proceedings and making false statements.

Paris Hilton was sentenced to probation for three years in 2007 for reckless driving. She also had to pay a $1,500 fine and attend alcohol education courses. But that wasn’t quite a good enough lesson because she got behind the wheel of a car again with a suspended license and while speeding.

For her day in court, she abandoned her glitzy party dresses in favor of something more sophisticated as if to say her partying days were behind her. Looking like she was about to head into a prestigious private school, this outfit couldn’t save her from a sentence of 45 days in prison.

Naomi Campbell has had a history of assault charges that were brought to trial after allegedly committing violence against employees. In 2007, she ended up getting a week of community service back in 2007 after pleading guilty to throwing a BlackBerry at her former housekeeper. She also had to pay her housekeeper's medical expenses and attend an anger management program.

For all of her court appearances, she appeared in her chic best, maintaining a look of professionalism that she displayed to the court. However, her behavior around her employees was decidedly unprofessional and the court could certainly not overlook that, even if she ended up being dressed to perfection while receiving her sentence.

Lindsay Lohan has probably spent more time in court than most celebrities and over the years she’s sported dozens of looks to win the favor of judges and juries. From Midi dresses to sheath dresses, elegant jackets to neutral-toned cardigans, Lohan pulled just about every trick in the bag.

Lohan was certainly at her boldest in 2010 when she went before a judge with a tie dye manicure with the words “F*** U” written on her fingernails. At the time she was in court for not attending her alcohol education classes, so I guess her strategy at that point was clearly to be as honest as possible…if  not too honest.

Cardi B showed up to court and certainly didn’t shy away from the fact that she’s a star. While some celebrities go with modesty to impress the courts, Cardi B went with pure glamour. One of her best outfits was a luxurious sleeveless crepe dress with a high neck, paired with wide-leg crepe pants, white sandals and a Hermès Birkin handbag. But this was her most memorable, a shirt and tie topped with a big, feathery, fluffy coat...

Her reason for being in court? The singer was accused of attacking two bartenders with bottles and alcohol at a New York Strip Club. For her appearance in court, she wore a range of elegant outfits as she is known while still being court appropriate. Although she denied involvement, she ended up being charged with assault and reckless endangerment.

Kim Kardashian showed her familiarity with the courts for her divorce hearing with Kris Humphries in 2013. She sported this conservative look at the Stanley Mosk Courthouse in LA. It’s ritzy and glamourous but as not to look like she’s trying too hard to look like a lawyer or too modest.

Sure, she’s probably showing less skin than she might normally, but the fact remains is that’s just how you dress in the courtroom. And it’s for the best that she didn’t try to dress like a normal person because, for better or worse, Kim is a celebrity and there’s no getting around that fact.

Anna Delvey, aka Anna Sorokin, dressed her very best when she showed up before the Manhattan Supreme Court. Although some might have dressed meek than chic to earn the court’s sympathies, she went a whole other way as if to show she had done nothing wrong. But it wasn’t all her idea.

For her lawyers, the goal was to dress her in something that didn’t scream “inmate” to the jury. So at first they picked something out from local H&M, but stylist Anastasia Walker, had something else in mind. Offering to help, Walker dressed her up in designer clothes. Blacks were chosen to convey seriousness and the choker was all Delvey’s idea.

In 2007, Nicole Kidman showed up to testify before New South Wales State Supreme Court, in regard to a defamation suit against celebrity photographer Jamie Fawcett. In her statement, she detailed an incident in which she was in a car chase with an aggressive paparazzo and nearly got into an accident – an incident that reduced her to tears.

Nicole Kidman dressed up plain and innocent to reaffirm that she is in fact a real person and not just a celebrity. While she could have dressed up looking as prestigious as possible to assert dominance, that wasn’t really the argument she was trying to make in court. This low-key attire was the best way to show the courts that she’s a victim and not the other way around.

Patty Hearst, a publishing heiress in 1974, was charged with bank robbery and the usage of firearms. According to Hearst, she was kidnapped by an organization called the Symbionese Liberation Army and was brainwashed into robbing the bank with an M1 Carbine rifle. She ended up serving less than two years in prison.

Her look was typical of ‘70s fashion, emulating celebrities like Diane Keaton, Jane Fonda and Anjelica Huston. The trendy look was undoubtedly used to make you think of celebrities like them and give her an appearance of normalcy. Apparently, the strategy did not pay off the way she wanted but she got minimal prison time, so it wasn’t all bad, right?

Nicole Richie was charged with a DUI in 2006 when she drove in the wrong direction onto an exit ramp. She had not hurt anyone but the incident did prompt her to change her partying ways. And in court, she was ready to convey that sentiment by changing her entire look.

Nicole Ritchie ditched her loose and free party clothes for something a little more stylish and conservative, a far cry from what was worn on her and Paris Hilton’s reality show “The Simple Life.” Her sleek courtroom weren’t just for show, however, as she has seemed to put all that behind her.

Blac Chyna, a model and socialite, went to court to take a stand against revenge porn. She took her ex Rob Kardashian to court to get a restraining order and ended up changing her whole usual look for something more conservative. And it ended up working to her advantage because she won her case.

Here you can see Blac Chyna dressed like a lawyer in the color white – purity. In a world that unfairly judges people by how they dress, this was a safe choice. She looks great and the courts could see that too. Now hopefully, she can rest easier now that she has a restraining order against her ex.

The late Amy Winehouse didn’t hold anything back when she went to court on charges of assault. She dressed just like herself, in an effort to show that she doesn’t have anything to hide. Her attire and demeanor conveyed the fact that she isn’t perfect but at the same time not guilty of the crime she was charged with.

It was no secret that Amy Winehouse battled with substance abuse and as a celebrity she battled with plenty of invasions of privacy. In 2009, one incident from an aggressive fan demanding a picture led her to defend herself by punching them. She plead guilty and claimed that it was indeed self-defense.