It’s not just about the horses at Britain’s most celebrated race meeting – as one redoubtable high-society dame demonstrated year-after-year with her outrageous millinery choices
Royal Ascot: silly hats. That is the prevailing wisdom, and the woman who did most to reinforce that image in the public consciousness was delighted by the impact she made. Gertrude Shilling added more to the gaiety of nations than would a million straight-faced models in designer couture.
After all, if you want to get ahead, get a hat. Shilling, a member of London’s high-society coterie, followed those instructions to the letter and became as much a focal point of Royal Ascot as the monarch herself.
At every royal meeting from the mid-1960s onwards, the gossip columnists and the society diarists and the paparazzi had eyes only for her. They called her the Ascot Mascot, and the likelihood of a photo of Mrs Shilling’s hat in the newspapers during race week was the best bet of the meeting, a sure thing.
Her unique headwear followed an annual pattern – big, unwieldy, outrageous, attention-grabbing, all made by her milliner son David, who began this labour of love as a teenager and whose riotous imagination was only matched by his mother’s chutzpah.
Where to start? There was the five-foot black top hat with a rabbit emerging jauntily from the top of it; a five-foot giraffe that swayed perilously in any breeze higher than Beaufort Scale 1.
Then there was a huge green apple with a four-foot arrow skewering it, an unexpected tribute to William Tell; a three-foot wide daisy with a tapering stalk embroidered down her back; a giant football for World Cup year; a vast sombrero; a picnic hamper containing plates of strawberries and champagne flutes; and a television, to advertise the advent of breakfast-time TV.
And don’t forget the collage of red, white and blue targets with a corsage of two doves of peace, to celebrate victory in the Falklands War; a dartboard; a colossal cup and saucer; a black and white cartwheel carrying the names of European nations to illustrate the Common Market, with her beaming face at the centre of it; an enormous paper sailing boat; and many more. You really didn’t want to be stuck behind her when trying to watch a race.
Shilling’s invigorating adventure in fashion was prompted by a diagnosis of breast cancer in 1966, at which point she was given 18 months to live.
Act of defiance
Her hats were an act of defiance, two fingers up to cancer, a celebration of life, and not, as the usual sour apples presumed, a display of exhibitionism or narcissism.
“I attended St Paul’s school in London,” David Shilling told the Daily Telegraph. “Art was really not on the agenda there. My mother allowed me to indulge my creative side by designing outfits for her.
“The outfits I made for my mother were really theatre rather than fashion. The early ones were quite extraordinary, three and four feet high, the product of a child’s imagination.
“She was great fun, incredibly energetic. A gay icon before the term was even thought of. She was terrified of wearing the giraffe hat, but it became a real favourite.”
In time, Gertrude Shilling saw off the threat of breast cancer, became the first woman in Britain to have a breast implant, a prosthetic shipped in from the US – “There is a little bit of me that is forever America,” she said – and carried on wearing her hats.
Whatever one thought of her outlandish headgear – and the catty, choleric Daily Mail diarist Nigel Dempster usually thought very little of them, once writing: “Mrs Shilling was up to her mad-hatter tricks again. She arrived in an outfit of such low taste that I am unable to bring myself to describe it” – Shilling displayed far more class and decorum than another memorable Ascot attendee, porn actress Linda Lovelace, the ‘leading lady’ of the notorious film Deep Throat (right).
The skin-flick siren arrived at Royal Ascot in 1974 in a Rolls-Royce Silver Cloud adorned with the numberplate PEN15, wearing a transparent dress with nothing on underneath. The occasionally irascible Bernard Fitzalan-Howard, 16th Duke of Norfolk, the Queen’s representative at the royal racecourse, had a few years earlier banned hotpants from the enclosures and drew an even thicker line at the prospect of no pants at all.
Prurient publicity
Thus Lovelace was denied her day at the races, but got all the prurient publicity she’d wanted. On another occasion she donned full top hat and tails but neglected to wear a shirt underneath. Perhaps she’d lost it on the favourite in the first race.
The Ascot authorities, never slow to regulate their customers’ attire, have formalised the dress code down to the last button, the last strap, working their way down the racecourse from the Royal Enclosure to the Windsor Enclosure, which lies farthest from the winning post and actually has no official dress code; simply getting dressed in the first place is probably sufficient.
The small print of their instructions is as absorbing as blotting paper. In the Royal Enclosure, ladies – not ‘women’ – may not wear a fascinator, although a headpiece with a base at least four inches in diameter is permitted. Shoulder straps must have a minimum width of one inch. Someone, somewhere, will be measuring carefully.
Nothing sheer is permitted – the tremors of the Lovelace effect are still capable of shaking society’s foundations – and midriffs must forever remain invisible.
Five-foot giraffe
The guidelines don’t mention accessorising a five-foot giraffe, which is a loophole surely worth exploring.
No-one would ever wear it as well as Mrs Shilling, though, who wore her inimitable hats to Royal Ascot until she was well into her eighties.
She was no aimless dilettante, either; she gave much of her time to charity and to entertaining the elderly, one hopes with glorious stories of Royal Ascot week and her son’s endlessly innovative inventions, and perhaps a tale or two about Linda Lovelace.
Gertrude Shilling died in 1999 at the age of 89, more than 30 years after being given 18 months to live, beating the odds as upliftingly as any plucky longshot.
Her legacy is the archetypal Ascot look, the one that encapsulates for so many the extravagant madness of the great race meeting. Hats off, you might say, to Mrs Shilling.
• Visit the Royal Ascot website
View the latest TRC Global Rankings for horses / jockeys / trainers / sires