Princess Anne rocks preppy knee-high socks and kilt in unearthed photo with tumbling hair

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Princess Anne, the Princess Royal, has spent decades dedicating her life’s service to the Crown. At 74, she is still considered to be one of the hardest working royals, completing a staggering 457 engagements in 2024 in light of King Charles’ reduced workload amid his cancer diagnosis. 

Yet aside from being a pillar of strength for her family, the Princess boasts an enduring sartorial legacy that will forever cement her as one of the best-dressed royal ladies. 

In her seventies, she continues to be one of royalty’s most prolific outfit repeaters, recycling bold 80s silhouettes, glittering ballgowns from her thirties and accessories treasured from the 1950s.

Princess Anne’s preppy kilt and butter-yellow sweatshirt

Rewind to 26 June 1998, when the Princess Royal and her then-husband, Mark Phillips were photographed at the Jackie Stewart Celebrity Challenge at Gleneagles Estate in Scotland.

© Getty
Princess Anne looks nearly unrecognisable with flowing long hair

The photograph is like a time capsule of the Princess’ former style file. Dressed in preppy knee-high socks and navy court shoes, the royal wears a blue and bottle-green kilt paired with a butter-yellow knit jumper. 

The royal wore her spring-hued knit layered over a crisp, baby blue shirt, accessorising with a navy leather handbag and felt fedora hat.

The Princess wore a striped shirt and butter-yellow cardigan at the Jackie Stewart Celebrity Challenge© Getty
The Princess wore a striped shirt and butter-yellow cardigan at the Jackie Stewart Celebrity Challenge

Given the Princess’ eco-style credentials and penchant for outfit repeating, it would come as little surprise if the mother-of-two were to recycle the exact outfit out – but one thing she’d never repeat is her tumbling Rapunzel-like hairstyle. 

In the photograph, captured when Anne was about 38, the Princess wears her brunette-wave hair in a half-up, half-down hairstyle. 

Princess Anne At The Jackie Stewart Celebrity Challenge At Gleneagles In Scotland in 1988.  © Tim Graham Photo Library via Get
The Princess Royal’s rarely-seen long hair is often pinned into a chignon

Princess Anne’s most loyal hairstyle

Recommended videoYou may also likeWATCH: 100 years of royal hairstyles through the decades

Anne, the only daughter of the late Queen Elizabeth II, is renowned for her steadfast commitment to her signature hairstyle – a sleek and elegant chignon. This classic updo has been her go-to style since her teenage years, rarely deviating from it throughout the decades.

While the infamous beehive has dipped in and out of style through the decades, the Princess Royal has remained its most loyal fan. She even had time to pin it up before leaving the hospital after giving birth to her children, Peter and Zara.

princess anne hair© Photo: Getty Images
Princess Anne’s chignon has become her most-trusted style weapon since the 60s

“It’s like armour,” Claudia Harrison (who plays Princess Anne in The Crown) told Marie Claire, who added that Anne’s loyalty to her perfectly executed ‘do is parallel with her unmatched work ethic and undisputed reputation as the hardest working royal.

It’s hard to picture the royal’s hair in anything other than the regal 1950s-inspired up-do, but the rare photograph captured from the archives shows its surprising length beneath her pinned ballerina bun. 

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