What Could Bring Diddy Down? Former Prosecutor Names Most 'Damning Evidence'
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Sean 'Diddy' Combs' Courtroom Fashion Is Subdued and Serious
Sean 'Diddy' Combs courtroom fashion is far different than the flashy looks he was known for while a free man. Is it strategic?
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Sean 'Diddy' Combs is back in court and this time he's wearing a suit. His simple, serious attire is a nod to the serious nature of the trial.
by Andrea Francese
Published on May 12, 2025
Sean âDiddyâ Combs is back in court for opening remarks. In the days leading up to his first court appearance last week, there was a fair bit of chatter about what he would wear. Days before the start of his trial, it was decided that the disgraced rap mogul could change into business casual clothing. Diddy, known for his flashy fashion sense and bling before his arrest, has opted for a far more subdued look for his courtroom appearances. The new look might be a nod to the seriousness of the allegations against him. It could also be a defense strategy.
Last Week, Sean âDiddyâ Combs made his first appearance in court, not wearing a prison jumpsuit. Jury selection, which began on May 7, found the Bad Boy Records founder wearing sweaters, collared dress shirts, and slacks. He opted to keep things mostly business casual during the first week. Now, though, his style choices are getting more formal. It coincides with his trial moving into opening statements.
While Diddy kept it a bit more casual last week, he has opted to show up to court for opening statements wearing a suit. According to sources inside the courtroom, Diddy entered the courtroom wearing a grey suit with a white button-down shirt on May 12. He has opted to accessorize with a pair of glasses. The suit is likely to get a lot of use as the trial progresses.
The now disgraced hip-hop legend will need to cycle through a few clothing options for the duration of the trial. Before the trial began, Judge Arun Subramanian approved a request from Combsâ legal team allowing him to receive non-prison clothing for his trial appearances. The approved wardrobe, however, was limited. Diddy is permitted to have up to five button-down shirts and five pairs of pants. He can also choose from five sweaters, five pairs of socks, and two pairs of shoes. His shoes can not have laces. Belts and other accessories were not mentioned.
Those who have seen Diddy in court note that he looks different from the day he was picked up by federal agents. Even in fresh clothing, he reportedly looks older, tired, and beleaguered. His hair has greyed in the months he has spent behind bars. His chosen court clothes are markedly different from how he presented himself before his arrest. In fact, just hours before he was arrested, Page Six captured photos of the rapper spending a day in the sun. There wasnât a grey hair in sight in those images. While some of his new look could be stress-induced, it might also be strategic.
An older, more serious look could be an attempt to make him appear relatable and harmless to the jury. Other high-profile defendants have tried the same. According to the Los Angeles Times, Harvey Weinsteinâs use of a walker and disheveled appearance were called into question. Similarly, outlets believed Bill Cosby tried to appear older and disoriented during his trial.
