Donald Trump Jr asked a courtroom sketch artist to "make me look sexy" after giving testimony during a $250m fraud trial.
The former US President's eldest son made the request after spending several hours on the witness stand during a second day of giving evidence at the civil hearing on Thursday.
Mr Trump Jr, 45, insisted he was never involved or aware of financial statements that New York state lawyers say fraudulently inflated his father's wealth and the value of the family business.
The statements were given to banks, insurers and other organisations to secure loans and broker deals.
Donald Trump, his company and senior executives - including Trump Jr and his brother, Eric, 39, who are both Trump Organization executive vice presidents and entrusted to run their father's empire - have all denied wrongdoing.
But the presiding judge, Arthur Engoron, has already decided in favour of the prosecution - with the hearing taking place to determine the punishment.
New York's attorney-general Letitia James is seeking a penalty of at least $250m (£205m) and a ban on Trump and his sons from running a business in New York.
When Trump Jr finished giving evidence, court sketch artist Jane Rosenberg revealed he asked her to produce a flattering portrait, telling her "make me look sexy".
He referred to an image she created of former cryptocurrency tycoon, Sam Bankman-Fried, who is a defendant in a criminal fraud trial.
Bankman-Fried was depicted with a chiselled jaw and spiky hair - which Trump Jr said made him look like a "superstar", Rosenberg told Reuters news agency.
During his testimony, Trump Jr said he believed his father's statements were "materially accurate".
He told the court the former president maintained the documents had "lowballed" his wealth and the value of assets, including skyscrapers, golf courses and properties.
He insisted he only dealt with financial statements in passing, signing them off as a trustee and giving them to lenders to comply with loan requirements.
Case is 'purely a political persecution'
And he reiterated that he relied on assurances from company finance executives before "signing off accordingly".
Speaking outside court, Mr Trump Jr said he believed his testimony "went really well, if we were actually dealing with logic and reason, the way business is conducted."
The case was "purely a political persecution", he told reporters.
"I think it's a truly scary precedent for New York for me, for example, before even having a day in court, I'm apparently guilty of fraud for relying on my accountants to do, wait for it...accounting."
Eric Trump also testified on Thursday, insisting he had "no involvement and never worked on my father's statement of financial condition", adding that he "didn't know anything about it, really, until this case came into fruition".
"That's not what I did for the company", he maintained - telling the court his role was focused on "pouring concrete" - constructing and operating properties.
On Thursday, Mr Trump - the front-runner for the 2024 Republican nomination - said on his Truth Social platform that the trial was "RIGGED" and branded it a "Miscarriage of Justice" and "Election Interference".
Ms James and the judge are both Democrats.
Mr Trump posted: "The Trump Organization is Financially Strong, Powerful, Very Liquid AND HAS DONE NOTHING WRONG."
The 45th US president - the only one to be impeached twice - faces legal cases in five different states across the country, with two separate actions in New York.