FASHION

Help? I’m 26 And Can’t Stop Dressing Like Princess Anne

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Riann Phillip

Some months ago, I arrived at the office in an outfit I quite liked: a vintage midi-skirt, a woollen brown check blazer and black knee-high boots. It felt entirely unremarkable – the kind of thing I’d worn countless times before. It wasn’t until I sat down at my desk, and fashion news editor Daniel Rodgers erupted into manic laughter, that I realised something might be afoot. “Is this a bad outfit?” I wondered, momentarily unnerved by the idea of getting it wrong in a place like Vogue. Then he let me in on the joke. “Riann,” he said, “why are you dressed like Princess Anne?”

There was nothing technically wrong with the outfit (in my opinion, at least). The issue was more existential: why was I, of all people, wearing it? I’m not a Sloane Ranger, nor a country-dwelling gal, and nor do I come from any ounce of inherited wealth. I’ve never been to Ascot, wasn’t privately educated and I really am no royalist. In fact, I’m pretty much an anti-monarchist. So, as Daniel later posited in a news story he wrote, why was I, “a politically-activated 26-year-old who listens to Shygirl”, dressed “as if she was bundling corgis into the back of a Vauxhall Astra on an exeat weekend in the Highlands”?

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The outfit in question.

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Princess Anne in September 2025.

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I would argue that, in the winter months, it’s almost impossible not to end up looking a little bit like Princess Anne. Sure, I like a T-shirt, baggy jeans and an Adidas Samba as much as the next 26-year-old, but I do also have an occasional affinity for the preppy. Does preppy automatically translate to Princess Anne cosplay? Am I unqualified to wear a tweed blazer because I’m from Coventry? Do you need to be a seasoned equestrian to pull off a riding boot? Is the Princess Royal’s style so distinctive that one “persnickety, shin-skimming skirt” (thanks again, Daniel) is enough to brand you a royal fanatic?

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Double denim and a bandana – a combination even Princess Anne couldn’t resist in the ’70s.

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A quick scan of Anne’s more casual looks will serve up comforting themes: sensible riding or Wellington boots, a crisp striped shirt, a hunting jacket (likely Barbour) and wraparound Oakley sunglasses. Unsurprising attire for someone living on a country estate in Stroud. Perhaps more strange if, like me, you live in Hackney and have never sat on a horse. As my colleague Olivia Allen recently noted, this countryside aesthetic is running riot in the city. “To me, the [Barbour] jacket will always be synonymous with drab dog walks in freezing temperatures, worn out of total necessity rather than stylistic inclination,” she wrote. “I can’t see the reason behind dressing like you’re off to the Young Farmers AGM when you could dress like a normal person.”

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Trench coat and riding boots – a woman after my own wardrobe.

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Alas, she may have a point. But like any enduring style culture, good old fashioned country casuals are unlikely to disappear anytime soon. Barbour jackets are everywhere on the Tube, Doc Martens has just released its first rain boot and Oakley sunglasses remain the default for It-girls marching up Kingsland Road. Quite frankly, Princess Anne deserves her plaudits for the unwavering commitment to a look so many of us have adopted. (Knowingly or otherwise.)

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Anne has never parted with her sports sunglasses.

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A fluffy baker boy hat and a million layers.

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As for why her style really is so compelling? I’d argue it comes down to practicality. A good, sturdy boot is hard to find these days, as are clothes that won’t fray or dull after a few washes. Perhaps that’s why most of the “royal” pieces I own are largely vintage or second-hand, and have lasted for years. After all, it was the famously frugal Anne – an enthusiastic outfit repeater long before Kate Middleton arrived on the scene – who said: “A good suit goes on forever. If it is properly made and has a classic look, you can go on wearing it ad infinitum. The economy is bred into me. My parents believe that things are not to be wasted.”

On the subject of her parents, it was her mother, Queen Elizabeth II, that had many feelings on clothing. “The Queen and I had a discussion the other day about the difference between fashion and style and I think maybe that’s relevant in the sense that she didn’t do fashion but she certainly does style, and style tends to last longer,” Princess Anne told an Australian magazine three years ago. “You have an individual style and it’s a quality which has a long-term value.” Which is to say, if you’re going to absorb a royal standard by osmosis, Anne is hardly the worst place to land. She’s the hardest-working and least problematic of the lot – she looks good, gets on with it and never makes a fuss. If I’m going to resemble any of them, I’m not mad that it’s her.

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McQueen

Tartan Wool Midi-Skirt

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Coor

Waxed Mill Coat

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COS

Suede Riding Boots

Oakley

Eye Jacket™ Sunglasses