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Prince Harry’s ex, Chelsy Davy, had the key to his heart from 2004 to 2011. In that time, Davy became well-acquainted with the royal family’s strict rules, including the expectations surrounding clothing. That said, she never had to adhere to royal protocol the way official royal family members like Kate Middleton and Harry’s eventual wife, Meghan Markle, did. But she was still likely mandated to keep modesty in mind when dressing.
Harry and Davy’s eventual breakup gave the Zimbabwean heiress more freedom to experiment with fashion, and one result of that was Davy’s revealing Halloween costume from 2016. But honestly, looking back, Davy was always wearing things that the royal family would have probably deemed inappropriate. Throughout her and Harry’s on-again off-again romance, Davy wore a plethora of short, flirty, feminine frocks that highlighted her long legs. And honestly, more power to her! What the late Queen Elizabeth II might have thought about her daring fashion is a whole other thing, of course, but we digress.
Here are some of Davy’s most leggy looks of all time.
Chelsy knows how to dress for night life
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Every “it” girl from the 2000s had an impressive romper collection, and Chelsy Davy was no exception. She threw on one of her rompers during a night out on the town in January 2007. The black and white look featured long sleeves, a matching belt, and an intricate pattern. Davy wore minimal jewelry and styled her hair straight. In case you were wondering, photographers captured her during a date night with Prince Harry (not pictured) at a London nightclub.
Chelsy rocked a summertime staple
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Chelsy Davy and Prince Harry used to bond over playing polo. Well, Harry played polo while Davy admired his athleticism from the sidelines. On this particular day, in July 2006, Davy embraced the summer temps by rocking a short pink tennis skirt paired with a multi-layered blue top. Given that July is usually the hottest month of the year, we’d say Davy was appropriately dressed, though we can’t help but wonder what the royal family thought.
Chelsy’s polo look was extra sultry
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Chelsy Daly dressed to impress in March 2006 when she supported Prince Harry at yet another polo game. As you can see, the heiress donned a super short asymmetrical dress that had a lot going on. Not only was it sheer, requiring a white lining underneath, but it also featured a ruffly fringe at the hem. Not to mention, the green number was decorated in a cool geometric pattern. Of course, she finished off the look by wearing a large pair of shades.
Chelsy ignored chilly temps for style
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Although Prince Harry and Chelsy Davy both attended Prince William and Kate Middleton’s wedding in April 2011, their love story had fizzled out completely the previous year. But Davy didn’t let the breakup (or awkward ex encounter) dull her shine. As you can see in the October 2011 photo above, she stepped out for a brisk fall night in London wearing a flowy white dress that stopped just above the knee. Although it wasn’t her leggiest look, the ruffled number was still much sweeter than some of the more rigid fashion that has come out of the royal family’s closets over the years.
Chelsy shined in a white romper
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In June 2016, Chelsy Davy celebrated the launch of AYA, her jewelry company, by wearing a gorgeous white romper. But unlike the one from several years earlier, this romper showed way more skin. In addition to being slightly shorter, it also featured patterned cutouts on the sides and sleeves. Then there was the plunging neckline! In a rare change, Davy gave her straight hair a break and embraced a shoulder-length curly hairdo.
Chelsy embraced festival fashion at Glastonbury
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Chelsy Davy was no longer the apple of Prince Harry’s eye in June 2016. But she was still all smiles as photographers documented her walking around Glastonbury Festival, which blends music, theater, and other artistic endeavors for attendees. Davy, of course, fit right in among the crowd by wearing a super short baby doll dress that stopped half-way up her thighs. She paired the loose-fitting orange number with shades and a pair of cowboy boots.