Sophie Rhys-Jones, a London PR executive, was just 22 when she first locked eyes with her royal beau, though it wasn't until several years later that their romance bloomed.
In a chance meeting in 1993 at the Prince’s Real Tennis Challenge event, Prince Edward is said to have secretly slipped Sophie his number.
Six years into their love story, the late Queen's son proposed with a £105,000 engagement ring - and the rest is history.
Duchess Sophie's post-engagement power suit
Duchess Sophie's post-engagement glow was evident in 1999.
Rewind to the day after she got engaged, it was business as usual for the hard-working cool girl who was seen commuting to her office job in London's ritzy Mayfair.
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Prince Edward's bride-to-be looked effortlessly chic in a fitted trouser suit in a creamy-green hue. She accessorised with a crisp V-neck blouse and added a delicate floral brooch to the lapel of her jacket.
Giving her daytime look a luxe feel, the royal-to-be teamed her corporate get-up with leather heeled boots, adding a waist-cinching black belt and dainty pearl earrings.
Proving a power suit never goes out of style, Sophie's sage trouser suit look can be seen on all of London's It-girls today.
A few days later, the Duchess was seen rocking yet another power suit, layering with a chic oversized black coat.
Her golden blonde choppy cut was a product of its time, with the late Princess Diana making the feathered pixie crop a millennial must-have.
The Duchess of Edinburgh formerly told HELLO! during an online event with the British Fashion Council that her own personal style icons blend both Hollywood and actual royalty.
When asked whose style she most admires, she said: "Angelina Jolie - I always think she looks amazing - and also Queen Rania of Jordan always looks stunning."
She added of British royal style in general: "Britain is an island – albeit a big island – and if you look at what royal women have worn over generations they have made huge fashion statements reflected from foreign shores, and that's what helps make our style."
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