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.
Sophie makes adorable comment about Prince Edward before their royal wedding
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.
Sophie Rhys-Jones lived in a swish London bachelorette pad before marrying Prince Edward
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.
Sophie returned to work the day after she said 'yes' to being Prince Edward's royal bride
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.
Princess Edward's bride-to-be stopped the presses outside her office
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.
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."