Zara Tindall was a 00s fashion icon in shoulder-baring Ascot dress

Zara Tindall is well-versed in dressing for the races, having accompanied her mother Princess Anne to Ascot for the first time aged eight in 1989.

By 2003, she had perfected her style, judging by unearthed photos of the mother-daughter duo. As we prepare for the five-day horse racing event to return to Berkshire in 2026, we're looking back at one of Zara's most chic race outfits, which has almost been forgotten.

Trailing behind her mother, the Princess Royal, who looked at ease in her peach skirt-suit, Zara kept a low profile in her black dress splashed with streaks of orange. With her blonde hair swept away from her face, she kept all eyes on her matching hat adorned with a large white flower.

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Although the 22-year-old royal's one-shouldered dress with a leg split technically wouldn't meet today's dress code, it was not against the rules at the time.

Ascot rules

Ascot fashion rules have evolved, with the official guide only released in 2012 and jumpsuits permitted from 2017 onwards.

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In 2026, the Royal enclosure, which has the strictest dress code of all the enclosures, states that dresses must fall below the knee, cannot be sheer, and must feature straps with a minimum width of one inch.

Matching trouser suits and jumpsuits are allowed, provided they follow the same rules, but necklines must not be strapless, halterneck or one shoulder.

Hat trends

Ascot is one of the few occasions when hats are not only advised, but actively encouraged to be as elaborate as possible.

In recent years, Zara has fully embraced this part of the dress code. Some of her most iconic headwear includes the statement Juliette Botterill black and white hat she paired with her fit-and-flare 'Camille' dress by Laura Green in 2025, and her exquisite pink floral headpiece by Australian milliner Rachel Henry in 2023.

Renowned milliner Jane Taylor, who has worked with Zara and the Duchess of Edinburgh, spoke to Best Quality Designer Handbag all about why the pillbox hat was trending last year.

"This summer, the world of hats and millinery is set for an elegant evolution. The classic pillbox hat, long associated with the Jackie Onassis-inspired styling of the ’50s and ’60s, is undergoing a modern transformation. 

"Instead of sitting toward the back of the head, this season’s pillbox takes on a more structured, minimalist approach, positioned higher and echoing the refined silhouettes of the 1980s," she said.