She was there to celebrate with the Queen when her horse Estimate won Royal Ascot's Gold Cup - the first time in the race's 207-year history that the title had been secured in the colours of a reigning monarch.
But Princess Eugenie is now preparing to step out of the world of royal privilege, butlers and caviar for a new life in America, the Daily Mail reports.
The 23-year-old granddaughter of the Queen has bagged herself a full-time job at a New York-based auction house Paddle8. Buckingham Palace refused to say what the job would be.
Patrons of the company, co-founded by Alexander Gilkes, include art world luminaries such as Damien Hirst and Jay Jopling.
In July 2012, Eugenie surpassed royal expectations by gaining her 2:1 BA Hons in English and History from Newcastle University. She also achieved a first in her final-year dissertation on the history of art.
"Since leaving university Eugenie has been committed to working in the arts world and has done some internships but is now set to take on a permanent role at graduate level," a friend of the Duchess of York said.
"From October she is going to work and live in New York, before returning to London where the company is setting up a new office."
The new opportunity, however, doesn't come without sacrifice.
Not only is she leaving behind the life she has grown to love but her relationship with Stowe-educated boyfriend Jack Brooksbank is likely to feel the strain of a long-distance romance.
"She is determined to be a working woman with a full-time job," the source added.
Eugenie joins her working older cousins, Prince William and Prince Harry.
The Duke of Cambridge is an RAF pilot and Harry is a Lieutenant in the British army.