Diddy has been ordered to explain why he needs fancy threads instead of jail-issued garments when he appears in federal court for sentencing on October 3, 2025, after a judge rejected his earlier attempt to wear civilian clothes for a separate hearing this week.

U.S. District Judge Arun Subramanian denied a motion from Diddy’s legal team to allow him to wear non-prison attire at his September 25 court appearance, saying the defense failed to provide a valid reason for the request.

The judge left the door open for the October sentencing but made it clear he expects a more detailed explanation before signing off.

Diddy’s attorneys submitted a scaled-back wardrobe request, asking the court to approve two button-down shirts, two pairs of pants, two sweaters and one pair of shoes without laces.

This is far less than what he was allowed during his criminal trial earlier this year, when he was permitted to wear up to five items of each type to avoid appearing in prison attire before a jury.

The October hearing will determine Diddy’s sentence after he was convicted on two counts of transporting individuals across state lines for prostitution.

The charges stem from violations of the Mann Act, a federal law that prohibits transporting people for illegal sexual activity.

The judge’s demand for justification reflects how federal courts handle inmate appearances, especially in high-profile cases involving celebrities like Diddy.

The court typically allows civilian clothing during jury trials to avoid prejudicing jurors, but the same leniency doesn’t always apply during sentencing.

Meanwhile, Diddy’s legal team is also pushing to overturn his conviction or secure a new trial.

His lawyers argue that prosecutors misapplied the Mann Act and failed to prove their case. They claim Diddy did not profit from prostitution and only paid escorts to perform with his romantic partners, which they say is protected by the First Amendment.

They also argue Diddy never transported anyone himself and did not receive money from the encounters.

Prosecutors counter that Combs directed and sometimes participated in the acts, secretly recorded them without consent and met the legal threshold for trafficking.

Judge Subramanian heard arguments on the motion to acquit or retry the case on September 25. As of presstime, he has not yet ruled on whether the conviction will stand or if a new trial will be granted.

Diddy has been held in custody since September 2024. His bail requests were denied due to concerns about potential violence and witness tampering.