His father Prince Charles famously tried on a rasta hat while visiting Jamaica - but got himself in a tangle by putting it on the wrong way round.
Now Prince Harry has proven he is a chip off the old block by attempting to speak Arabic in the Middle East but getting himself tongue-tied in the process.
The 29-year-old prince was guest of honour yesterday at a fundraising dinner in Dubai in aid of his charity Sentebale, which he co-founded with Prince Seeiso of Lesotho to help children affected by the HIV virus.
To impress his 300-strong audience, who included members of Dubai's royal family, dignitaries and wealthy business leaders, he tried a few sentences in Arabic but found himself stuttering over the guttural pronunciation.
He began by wishing them: “Asalaam alaikum, masah al khair, marhaba” which translates as: “God be with you, good evening, hello.”
Prince Harry then half-muttered under his breath on stage: “Hopefully that was right, I’m not sure. Probably not.”
But after a 10-minute speech in his native tongue encouraging his audience to bid generously in an auction at the Forget-Me-Not dinner, he felt brave enough for a second try.
He said in Arabic: "Thank you for your generosity and all the best with Dubai's 2020 bid," referring to the city's ambitions to host World Expo 2020.
Even though the Arabic-speaking members of his audience were less than impressed with his accent, they broke out in applause at his attempt to master their language.
Dubai resident Jamal Laaloui, 35, originally from Morocco, said: “It was not pure Arabic and his accent was not authentic at all.
“You could definitely tell he was not an Arabic speaker.”
Marleine Ramadan, 25, from Lebanon, added: “It was hard to make out what he was saying as he was speaking modern standard Arabic rather than colloquial Arabic but it is a good thing he tried at all.”
The prince told the gathering the charity was close to his heart and said he hoped to help thousands of children, adding: “It has been a life-changing experience…your money is not being thrown into a box where you never know where it is going to go.”
He ended his speech by saying: “Shukran.”
Earlier the prince roared with laughter on the red carpet when asked whether he planned to propose to girlfriend Cressida Bonas.
Speculation has been mounting about whether he will be following in his brother William’s footsteps by settling down.
But he refused to be drawn and instead guffawed while blushing pink at the question posed to him at the latest stop of his worldwide tour.
Prince Harry, dressed in a tuxedo, was in Dubai on his way back from Australia to host the event for Sentebale at the JW Marriott Marquis hotel, which was attended by a number of dignitaries and celebrities.
They included newly-single British TV star Denise van Outen, singer Joss Stone, who performed on the night, and Prince Seeiso.
Prince Harry was flanked by Sheikh Ahmed bin Saeed al Maktoum, the head of Emirates Airline and Emirati businesswoman Raja al Gurg, as he went into the hotel’s ballroom.
He spent an hour beforehand meeting key Dubai business leaders, including fellow old Etonian Tom Hudson, who founded British Polo Day, with his wife Jessica.
Mrs al Gurg said on stage: “With the support and generosity of many UAE nationals, we hope to improve lives through health and education.”