Bring back the bad celebrity. The DUIs, the defamation lawsuits, the drug charges, and drawn-out divorce battles. Enough of Emily Ratajowski and her Amia Srinivasan cosplay, Jameela Jamil, her infographics, and “Imagine”. What happened to dirty diamonds, low grade scams, and Patrizia Reggiani? 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. Misogynistic, of course, but whether these women were caught texting at the wheel, shoplifting, or huffing slugs of white powder, they simply refused to be punished. 

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” this week. 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.