Princess Anne, the Princess Royal, has dedicated her life to serving the Crown, and at 74, she remains one of the hardest-working royals, completing an impressive 457 engagements in 2024, especially in light of King Charles’ reduced schedule due to his cancer diagnosis.
Beyond her unwavering support for her family, the Princess has cultivated a lasting sartorial legacy that sets her apart as one of the best-dressed members of the royal family.
Even in her seventies, Princess Anne continues to be a prolific outfit repeater, often recycling bold 80s styles, stunning ballgowns from her thirties, and cherished accessories from the 1950s.
Looking back to June 26, 1998, a charming photograph has resurfaced of Princess Anne and her then-husband, Mark Phillips, taken at the Jackie Stewart Celebrity Challenge at the Gleneagles Estate in Scotland. This image serves as a delightful glimpse into her past fashion choices.
In it, the Princess sports preppy knee-high socks and navy court shoes, complemented by a blue and bottle-green kilt and a butter-yellow knit jumper layered over a crisp baby blue shirt. She accessorized with a navy leather handbag and a felt fedora hat.
Given her commitment to sustainable fashion and her penchant for outfit repetition, it wouldn’t be surprising if the mother-of-two decided to wear this exact ensemble again—but her iconic, cascading hairstyle is something she wouldn’t repeat.
In the photograph from when she was about 38, Princess Anne showcases her long, brunette waves styled in a half-up, half-down fashion.
While Anne is best known for her commitment to her signature sleek chignon—an elegant updo she has sported since her teenage years—this rare archival shot reveals surprising length beneath her pinned ballerina bun.
Claudia Harrison, who portrays Princess Anne in The Crown, described her hairstyle as “like armour” in an interview with Marie Claire, emphasizing that Anne’s dedication to her meticulously crafted look mirrors her legendary work ethic and reputation as the hardest-working royal.
It’s hard to envision her hair styled any differently than the classic 1950s-inspired updo, making this snapshot a unique look at her style evolution over the years.
