How to look classy in cold weather like Princess Anne
In fashion circles, there is usually a strong preference for winter dressing. After all, it’s easy to look chic in a great coat, cashmere knitwear and well-cut boots. But it’s a delicate balance: if the mercury drops too low, then you’re in danger of going full-on Michelin Man. Almost no one looks good in four jumpers, thermal leggings, trousers, two pairs of socks, balaclava, gloves and coat – accessorised with a red nose.
Yet staying warm while also looking stylish needn’t be mutually exclusive concepts when it comes to our wardrobes. One person who knows this to be true is Princess Anne, who can always be relied on to be dressed both practically (you wouldn’t catch her with no tights in November) and with sartorial flair.
“She likes classic tailoring, bold patterns, bright colours, and often re-wears outfits she has had for decades, showing her support for sustainability before it became a trend,” says Royal Fashion Police (an Instagram page for followers of Royal fashion) of Anne’s style. “Her wardrobe includes vintage pieces, statement hats, classic bags and practical shoes, focusing more on comfort and function than following trends.
“Practical footwear, such as sturdy boots for outdoor engagements or comfortable low heels for formal occasions, is a staple in her busy schedule. She completes her outfits with silk scarves, brooches, classic handbags and statement hats when needed, maintaining a timeless and elegant style.”
Princess Anne gave a masterclass in stylish cold-snap dressing over the weekend, when she once again appeared at church in Sandringham alongside her brother, King Charles III.
The surprising sartorial detail here was the bobble hat – an item that you might expect to see your Gen Z daughter wearing rather than a septuagenarian member of the Royal family – worn with a monotone dark grey skirt suit.
As with her choice of a bucket hat for the Paris Olympics, it’s the bobble hat that acted as a point of difference, as a go-to accessory for 20-somethings in slouchy loungewear.
Yet the Princess Royal makes it look grown-up by matching it with the rest of her look, allowing the scarf to be the one pop of colour. It’s practical, without looking like she’s ready for a spot of snowboarding – thanks to the rest of her ensemble.
Throughout the winter months, Princess Anne has frequently delivered a masterclass in sub-zero, peak-chic dressing. Her Christmas Day outfit was case in point. Photographed at St Mary Magdalene Church in Norfolk alongside her husband, Vice Admiral Sir Timothy Laurence, and the wider Royal family, she was notable for her incredibly elegant – yet definitely practical – look.
The 74-year-old chose a festive red fitted jacket, featuring a high neckline (always useful when it’s bracing outside), which she paired with a grey-and-navy tartan kilt skirt.
Yet it’s her accessories that really elevate the look: that matching red wool scarf, draped elegantly over her shoulders, rather than tied in a knot, plus knee-high suede boots, simple black gloves and a brand new £375 faux-fur hat from Lock and Co.
By co-ordinating her accessories so that they fit into the tonal colour palette of the rest of her outfit, she ensures she avoids looking like she just threw on everything she could to stay warm.
Meanwhile, her classic jewellery – pearl-drop earrings and a knotted gold brooch (a gift for her 40th birthday in 1990) – elevate things and keep it refined.
One of her favourite styling tricks, as demonstrated at Cheltenham in both 2019 and 2024, is to wear a brightly coloured silk scarf with a natty print. Worn with a contrasting colour coat, visibly tied at the neck or hanging loosely, it’s something straight out of the sartorial playbook of her late mother, Queen Elizabeth II and late aunt, Princess Margaret.
The addition of a silk scarf works wonders at transforming something fairly run of the mill into something a little special. Another of her go-to formulas is to add lots of brooches, hat pins or necklaces, so that there is something to distract from all the more robust and practical wool and tweed at play – and perhaps even trick the casual observer into thinking it’s warmer than it actually is.
Inspired? There’s one more element left. The pièce de la résistance loved by not only the Princess Royal but the international jet set (see: Jennifer Lopez, Kevin Costner and Mariah Carey in Aspen right now)? A pair of sunglasses. They make everyone instantly look a tad more glamorous in wintry environs – whether the eyes behind them are streaming with cold or not.
