Diddy's ‘cosy sweater strategy' and why trial style actually matters

Telegraph

9 hours ago

Every morning when we stand in front of our wardrobes choosing what to wear, we make a series of decisions about how we want to present ourselves to the outside world: a tailored suit, for example, is often used to symbolise power. A tracksuit? Not so much.
But never does 'a look' convey more than the sum of its parts than when it's worn in the high-stakes environment of a trial. Then it's not fashion, but carefully choreographed 'courtroom strategy' to let your clothes speak before you do.
Take Sean 'Diddy' Combs, found guilty on Wednesday of two counts of transporting people for prostitution, but acquitted on the more serious charges of sex trafficking and racketeering, after an eight-week trial in Manhattan federal court. Combs, in the face of disturbing and lurid allegations spanning multiple years and several alleged victims, made a concerted effort to distance himself from his blinged-up alpha male hip-hop mogul image of old. Gone were the 'player' silken tracksuits, the confident heavy gold jewellery, the 'cartoon villain' OTT frills and grandeur of the floor-length black embellished coat featuring 600 Swarovski crystals and black pearls which he wore to the 2023 Met Gala – a custom piece from his own fashion label Sean John.
Instead, court sketches showed the multi-millionaire music impresario sporting grey hair and a short grey beard (prison rules forbid hair dye), black rimmed studious-looking spectacles and soft sweaters in a range of sensible colours – beige, navy and grey; with the collar of a white shirt worn beneath the only notable feature. One day of his trial he sat patiently reading the Bible, a far cry from the ' freak-off ' swinger lifestyle he confessed to having enjoyed prior to his arrest.
Who knows whether this appearance was a hitherto unknown quirk of Diddy's personal brand or part of what's been termed 'the nerd defence' by its originator lawyer Harvey Slovis (who once represented Mr. Combs during his trial on charges of gun possession in 1999). Either way, the phrase refers to the idea that glasses – accessories associated with thought rather than aggression – have a subliminal effect on a jury, predisposing them to assume a lack of guilt.
Consider, too, his knitwear which took the 'just a regular guy'-vibe to a whole other level. Quite literally soft and cuddly, jumpers have been employed at several gruesome trials, from that of the Menendez brothers in 1993 (accused of shooting their parents) to those of Combs and Luigi Mangione, on trial for the murder of UnitedHealthcare CEO Brian Thompson. In December 2024 Mangione, a case in point of the power of personal image, donned a sensible all-American boy next door uniform of a burgundy crewneck and khakis to face 11 charges including first degree murder and the furtherance of terrorism.
Sweaters aside, disgraced former movie mogul and convicted sex abuser Harvey Weinstein has a strategy of his own, appearing a dishevelled shadow of his once-imposing self each time he appears in court on rape charges. Sometimes seen struggling up the courtroom steps stooped over and using a walking aid, in April this year a hospital band indicating he was a 'fall risk' hung out of his suit sleeve in full view of the court.
'Everything in a courtroom serves a symbolic purpose, including the wigs and robes of the legal profession – the use of wigs has been in place since the 17th century and judges robes date from much earlier than that,' explains Dr Liza Betts, senior lecturer in cultural and historical studies at London College of Fashion (UAL). 'They are used to convey formality and to distinguish status and power. As the courtroom is so symbolically loaded it makes sense that the clothing of everyone present will be read in the same way – subject to the level of fluency someone might have in the language of dress being employed.'
These men are not, of course, the only people to use the soft power of their appearance to convey a subliminal message in a legal setting.
It was Jacqueline Kennedy Onassis who deftly mastered the art of trial style when, in 1972, the former First Lady sued New York's 'most unrelenting' paparazzo Ron Galella for public harassment, both of her and her children. Appearing in front of the judge, she cut an elegant, dignified figure bedecked in wool coats and button-up jackets. Onassis successfully obtained a restraining order against Galella (which he did not respect, causing the pair to later meet again in court).
In 2002, actor Winona Ryder pushed the envelope when it came to courtroom dressing, entering fashion lore. Charged with shoplifting thousands of dollars' worth of goods from Saks Fifth Avenue, including pieces by Marc Jacobs, the star arrived at shoplifting trial dressed in a trompe l'oeil knit dress by none other than Marc Jacobs himself. Throughout proceedings, Ryder sported headbands, buttoned-up jackets over midi skirts and mid-height heels. Instead of three years in jail, the judge handed down a sentence of three years' probation and a fine.
Billionaire reality star Kim Kardashian's appearance at a courthouse in central Paris last month is another case in point. There to give evidence in her own robbery trial (more than £7 million of jewellery was stolen from the star during a five-hour armed robbery ordeal in a Paris hotel in 2016) the American socialite turned up in a figure hugging power suit dripping in an estimated £6 million worth of jewellery.
Arriving alongside her mother Kris Jenner to testify against the so-called 'grandpa robbers' – a group of nine men and one woman, with an average age of 70 – Kardashian donned a pair of Alaïa sunglasses, a waist-cinching vintage John Galliano black skirt-suit with a peplum and plunging neckline and slingback heels from Saint Laurent.
Around her neck she wore a tear-drop diamond necklace containing a reported 52 carats of stones by New York-based rare diamond specialist Samer Halimeh alongside diamond earrings, including a 4.55 carat diamond over the ear cuff from Repossi and a £6,000 white gold and diamond pavé version by Briony Raymond.
'Ultimate power move,' said Raymond on her Instagram account regarding Kim Kardashian's appearance in her wares. 'A nod to jewelry as armour and a defiant statement that proves she will not be robbed of her love of jewelry and the joy it brings her.'
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Not to mention, of course, Kardashian's ability to simply replace stolen gems worth millions of dollars and flex them in front of the accused.
'Clothes do communicate, we use them for this very purpose,' continues Dr Betts. 'To say who we are, who we think we are, who we would like to be, who we are told to be, or who we think others would like us to be.'
Earlier this year, rapper A$AP Rocky appeared in a Los Angeles court facing charges of two counts of felony assault. Rocky arrived at his trial looking incredibly chic, as you would if you'd been kitted out in top-to-toe Saint Laurent (some items costing almost £4,000) by the brand themselves. Rocky was latterly found not guilty. Just goes to show, there truly is no such thing as bad publicity.
The examples are numerous: Gwyneth Paltrow curated her courtroom image (soft, approachable in cashmere and wool from stealth wealth brands such as her own label Goop, The Row and Celine) after a personal injury claim resulting from a skiing accident saw her in front of a judge in 2023.
Then there's fake heiress Anna Delvey – found guilty of grand larceny in 2019 after seducing Manhattan's glossy elite out of hundreds of thousands of dollars to fund her make-believe ventures – who employed the services of stylist Anatasia Walker to help create her courtroom 'look', which on day one consisted of a beige sweater, choker necklace and black dress that the New York Post claimed was from Miu Miu. 'Anna and I talked on the phone about what she was interested in wearing,' Walker told ELLE.com at the time. 'I couldn't show her photographs, but as people interested in fashion, we spoke in references about the themes she wanted to come through [in her outfits].'
New York Times fashion critic Vanessa Friedman notes that for those who don't regularly wear suits, donning one just to court in a pass notes bid for respectability can often backfire (in a departure from his normal style, R&B singer and now convicted sex abuser R Kelly wore them for his court appearances in 2021, ultimately being found guilty).
But then again, so can being your authentic self.
Martha Stewart who got it all wrong in 2004, turning up to court toting a £7,500 tan Hermès Birkin bag, multiple long strands of cultured pearls and a fake fur stole to defend herself against charges of insider trading. 'The Birkin did little to promote the image of an approachable woman who has struggled up from humble roots,' wrote the New York Times at the time. 'Instead, it cemented an image of her as a pampered fat cat seemingly willing to snatch money from an Average Joe Stockholder.' Stewart was convicted of obstruction of justice and lying to investigators and sentenced to five months in prison and two years' probation.
Not only did Heather Mills McCartney defend herself during her divorce proceedings in 2008, but she also made her own three-piece suit to wear to court which apparently took inspiration from a court jester. But it seems Mills McCartney – who also threw a glass of water over Paul McCartney's divorce lawyer, the infamous Fiona Shackleton, in court – had the last laugh, walking away from proceedings with a cool £24.3m divorce settlement.
The semiotics of courtroom style can sometimes reach the wrong audience. While battling addiction in the Noughties, actor Lindsay Lohan had multiple court appearances for earlier offences of driving under the influence which were heavily followed by the tabloid media. During one, in 2010, the star sat with her lawyer staring down press photographers with nails manicured with the words 'F--k U'. Whether or not the judge also read her not-so-subtle message is not known, but Lohan was sentenced to 90 days in jail.