Princess Anne’s Best Fall Fashion Over the Years — From Wool Coats to Heritage Tweed

The Princess Royal offered a study in country-chic dressing at its most practical on day three of the Whatley Manor Horse Trials at Gatcombe Park, her Cotswolds estate, in September 2018. Anne dressed practically a green tweed vest layered over a plaid shirt and turtleneck, with matching trousers and sturdy outdoor boots.

A lifelong equestrian and former Olympic competitor, Princess Anne visited the Hambleton Equine Clinic in Stokesley, North Yorkshire in October 2017, dressed in a grey patterned suit co-ord with a turquoise silk neck scarf, black leather gloves, a shoulder bag, and tall boots.

Cheltenham Racecourse is one of Princess Anne’s most reliably attended autumn engagements, and in November 2015 she marked a particularly special occasion there—the opening of a new stand named in her honor, part of a £45 million ($60 million) redevelopment of the venue—dressed in a double-breasted grey-beige coat, red roll-neck, black leather gloves, and a dark fur hat.

A bright red-orange coat, dark fur hat, and her signature gold horse brooch made Princess Anne one of the most eye-catching figures at the Hennessy Gold Cup Race Day at Newbury Racecourse in November 2013.

Dressed for the lighter temperatures of early autumn, the Princess Royal attended the Freedom Parade of 11 Explosive Ordnance Disposal Regiment—a specialist unit of the British Army’s Royal Logistic Corps—in Oxfordshire in October 2013, wearing a red button-down jacket paired with a maroon pleated skirt.

At the Hennessy Gold Cup at Newbury Racecourse in November 2011, Princess Anne cut a characteristically practical figure in a double-breasted grey tweed coat, matching hat, dark gloves, and black leather boots. She is pictured alongside Andrew Parker Bowles, the first husband of Queen Camilla, with whom Anne has maintained a close friendship for more than 50 years after the two briefly dated in the 1970s.

An umbrella is as essential as any brooch in the British fall wardrobe, as Princess Anne demonstrated at Ascot Racecourse in September 2007, where she attended a race meeting in her capacity as patron of the Injured Jockeys Fund, dressed in a dark coat, black hat, burgundy scarf, and black boots—brolly firmly in hand.

At the unveiling of David Backhouse’s Animals in War memorial at Brook Gate, Park Lane, in November 2004, Princess Anne arrived in a cherry-red double-breasted cropped coat with a high collar, a pleated tartan skirt, knee-high black boots, and matching black leather gloves and handbag.

The Princess Royal arrived to open Pringle of Scotland’s new Bond Street boutique in London in November 2002 in a palette of classic fall colors, with a brown houndstooth blazer featuring contrasting lapels, a printed silk scarf, dark gloves, and a traditional red poppy pin for Remembrance Day at her chest.

Not an obvious autumn choice, but a striking one as Princess Anne wore a lovely long Wedgwood blue coat and patterned silk scarf while inspecting horses at an event in London’s Hyde Park in November 1989.

Although Princess Anne competed as an equestrian at the highest level —including at the Olympics—she has also long mastered the sideline look (today known as the “horse girl aesthetic”) that so many spectators strive to emulate, as seen at the Royal Chase benefit equestrian event in Nashville in November 1987, where she wore a double-breasted coat over a light turtleneck, her signature gold horse brooch pinned at the lapel.

Mastering travel style in this cape dress, Princess Anne was photographed at Heathrow Airport, departing for Dubai in November 1984.

Princess Anne and her then-husband, Captain Mark Phillips, attended the Chatsworth Horse Trials at Chatsworth House in Derbyshire in October 1977. It is hard to tell under her Barbour jacket, but Anne was pregnant with her first child, Peter, at this time.

Princess Anne, seen here in this lovely photograph from November 1974, is wearing the number one fall accessory: a good hat.