In pictures: Tracing celebrity courtroom style22 Images
A version of this article was published on 20 February 2025
To see a celebrity emerge from a throng of photographers and creep into a courtroom – flanked only by a sensible handbag and a lever arch file – is to gawp at a sportscar smoking on the motorway. It’s grim and fascinating, glam and tragic, upheld by the sidebar of shame and fuzzy TMZ videos. That feeling was laid bare this week, as Cardi B emerged from a New York courthouse victorious, cleared of a $24 million civil assault charge. Styled by longtime collaborator Kollin Carter, the rapper wore Valentino by Alessandro Michele, her polka dot power suit entering a long lineage of celebrities leveraging fashion in the eyes of the law.
Be it Martha Stewart or Tulisa Contostavlos, fashion is an instrument of persuasion in any star offender’s armoury. Consider Cardi B in a marabou-feathered cape or Lindsay Lohan with Fuck U painted in microscopic lettering on her fingernails. To take control of your appearance while in the grips of disgrace feels cocky, disobedient, and powerful. Transforming and twisting a trial into a PR moment – see Naomi Campbell doing community service in a glimmering Dolce column gown – seems to ridicule and undermine the seriousness of the judicial system. It’s the ultimate media circus whereby the celebrity, not the press, is ringmaster, landing magazine covers via Peter Pan collars, saucer sunnies, and an entire can of Elnette, all while channelling Audrey Hepburn for judge and jury. It’s all about looking reformed and demure, innocent even if proven guilty.
The campy tradition of courtroom dressing, honed by the likes of Winona, Lindsay, and Paris is an art, which is to say it’s curated, considered, and diligently crafted. In fact, just a whiff of the slammer is enough to get a styling team pulling racks of monochromatic looks, like Anastasia Walker who wardrobed Anna Delvey in 2019. “I really tried to focus on classic silhouettes and classic pieces in general,” she told Elle in an interview at the time. There are limits to all of this, however, like when the Daily Mail lauded Ghislaine Maxwell’s “pretrial makeover” and “freshly-dyed bob” in late 2021. Some things cannot be papered over with a nude gloss and an ivory pant suit – alleged sex trafficking is one of them. Either way, strategic, courtroom style dins with the very psychology of fashion, to both project and protect. Below, we take a look at the most legendary examples of courtroom costuming, from Courtney Love, to Linda Evangelista, and Anna Nicole Smith.
Amidst the rollout of her upcoming album Am I The Drama?, Cardi B has been embroiled in a spot of additional drama, namely a $24 million civil assault case. Other than details of the alleged 2018 incident – of which Cardi has now been cleared – another point of interest was the clothes the rapper was wearing. Like legions of celebrities before her, Cardi leaned into the courtroom power suits – a grey tweed set with a feathery blazer on one day, a white nipped in jacket on another, and a polka dot Valentino suit on the last day of court. While by no means inconspicuous, by Cardi B standards the clothes we pared back, borrowing from the playbook of stars dating back to the 90s, who communicate innocence through monochromatic palettes and serious silhouettes. Scroll down for our pick of the bunch.
Back in February, A$AP Rocky was found not guilty in his LA trial, where he stood accused of two felony counts of assault with a semiautomatic weapon in 2021. Due to the serious nature of the trial, the majority of reporting focused on the charges rather than the celebrity circus surrounding them – however, once the verdict was announced, this seemed to give commentators free reign to discuss wider topics (i.e. the fashion). Rocky’s carousel of Saint Laurent suits were brazenly confident exuding a striking confidence and drumming up press for the brand. Though it’s the most recent case of a celebrity leveraging fashion in the courtroom, it’s most certainly not the first – scroll through the rest of the gallery for nine more examples.
Throughout the 2010s, LiLo’s court appearances evolved into must-watch Hollywood events and featured a carousel of styles, which were as multitudinous as her misdemeanours. First coming into contact with the judicial system in 2007, her looks span presidential, bell-bottomed suits worn with a taut chignon bun, and bright white bodycons, platform stilettos, with her bleach blonde hair scraped into a loose ponytail. Her most controversial of statements, however, was to paint Fuck U onto her nails, which she debuted at a probational hearing in 2010. The actor claimed that the manicure was entirely unintentional, of course. “Didn’t we do our nails as a joke with our friend?” she tweeted to a friend. “It had nothing to do w/court … it’s an airbrush design from a stencil.”
Though she is now lobbying in court, Paris Hilton has had a fair few run-ins with the law, including a guilty plea on drug charges, no contest on a DUI, and a sentence to 45 days in jail for violating a driving probation. Ever the business woman, Hilton donned a litany of monochromatic cocktail dresses for her hearings, comprising bow-detailed necklines and plunging, ecru blouses – looks which wouldn’t go amiss on any given commuter train from Waterloo. Paris’ most iconic look, came when she was summoned to court for violating probation. With a Chanel flap hooked over her shoulders, she wore a cropped, pinstriped blazer, a shrunken waistcoat, and wide, high-waisted bottoms. Walking hand on hip into a Los Angeles courthouse, her face was obscured by giant sunglasses, her hair pushed back with a shiny, patent band. It was peak 2007 and peak Paris.
The subject of upcoming Netflix series Inventing Anna, scammer supreme Anna Delvey’s courtroom looks were so inspirational that Instagram account @annadelveycourtlooks has been raised in her honour. There, Saint Laurent sheer shirts, Michael Kors shift dresses, big glasses, and little chokers alight the grid alongside H&M sweaters and office-y Uniqlo pants. Despite there only being four looks in total, the account has amassed nearly 10k followers, reflecting our lurid obsession with the Soho Grifter and the matrix of lies, betrayal, and forged finances at the heart of New York’s social scene.
In 2019, Cardi B stood before a New York tribunal, having been invited to court over an alleged fight which broke out in one of the city’s strip clubs. Never the wallflower, Cardi sauntered into the building in a mammoth, hooded coat, which had been ladened with feathers and trailed down the courthouse’s rain-slicked steps. Designed by Adrienne Landau, the rapper paired the imposing Sesame Street creation with a white button-down, slim-fit trousers, and a pair of Christian Louboutin stilettos. Much like how a bird fans and ruffles their feathers when under attack, Cardi flexed her fashion fluency in an ultimate distraction display.
Back in 2002, Winona Ryder trundled into Saks Fifth Avenue with “more pain medication in her purse than would be given to a person with a terminal disease” and stole thousands and thousands of dollars worth of merchandise. As a result, she was tried for grand theft and vandalism, though she escaped the trial with no jail time – just probation and a fine. Though she later blamed the event on a “quack” doctor who had wrongly prescribed her medication for a broken arm, all those sensible headbands, twee two-piece sets – embroidered with little flowers and bows – and Mary Jane pumps, which she wore to trial practically screamed innocence.
Following the death of her 90-year-old, billionaire husband, an extraordinary legal battle was set into motion. Despite not being mentioned in the will, Anna Nicole Smith requested a share of her late husband’s probate, while her ex-husband’s stepson fought against her claim. Cue some of the most legendary court looks to date. Enormous sunglasses paired with tailored, ivory two-pieces spoke to power and authority, where Smith was not capable – she was almost illiterate and struggled to keep up with the text-heavy court proceedings. Snuggly, thick-ribbed knitwear and cardigans embodied a certain humility, reliability even, as she clutched photos of her former husband to her chest. It was the proto-sartorial strategy of Paris Hilton, Lindsay Lohan, and Nicole Ritchie, which centered purity and virtue, without skimping on magnetism.
Over the years, Courtney Love has been ordered to court for a score of alleged incidents involving drug charges and defamation lawsuits. Her looks have varied from punk to conservative, to something of a punk-conservative, which is to say she has worn lilac tweed suits, belted tube tops, and flouncy, psychedelic skirts with slits up to the hips. Lest we forget, this is a woman who once piped, “I am God and my lawyers are my twelve disciples, do not fuck with me.”
In 2013, Nigella Lawson confessed to taking cocaine exactly two times in her life, playing into the time-worn tradition of celebs publicly counting the number of occasions they have taken a bump. Lindsay Lohan famously told Oprah that she had taken coke no more, and no less, than “ten to 15 times”. On the day of trial, Lawson stormed into a London court to give evidence against her former PAs, who were facing fraud charges. Bolstered by a hefty entourage of hard-capped police officers, Lawson bled into the monochromatic crowd, looking impeccably-presented in an ankle length trench coat, accented with a whisper of a white collar, a sweep of rouge, and a professional, barrel brush blow-dry. Now that’s power.
Embroiled in a child support battle with François-Henri Pinault of Kering, Linda Evangelista arrived to a family court in Manhattan in 2012, demanding $46,000 a month settlement, while wearing a prim, floral swing jacket and white pencil skirt, worn back with a classic Chanel bag and Louboutin pumps. Throughout the week, Evangelista leaned into a Jackie O wardrobe, consisting of flowered silk blouses and polished knee-length skirts. These pricey looks earned the supermodel criticism from the media, who saw a dissonance between Evangelista requesting financial aid from her billionaire ex-husband and her designer outfits. “Linda Evangelista may have schemed to project the image of a woman wronged. If so, she missed the mark,” the New York Times said.
