30 Vintage Photos of Mrs. Gertrude Shilling Wearing Eccentric Giant Hats for Years at Royal Ascot Racing Events

Considered now to be one of the greatest milliners and hat-makers in the world, the hats David Shilling designed for his mother Gertrude to be worn at Royal Ascot in the 1960s, 1970s and 1980s were anywhere from over the top, to avant-garde, to just plain insane!

For 30 years, until she was well into her 80s, Gertrude Shilling appeared at showy events in towering creations that took imagination to design and construct, and a very determined sort of cheek to wear. There was the five-foot tall giraffe design that she pioneered in the 1970s, a three-foot wide daisy hat – with a stalk embroidered down the back of her coat – and a massive concoction of an apple with a four-foot arrow pierced through it.

Gertrude Shilling was made for exaggeration. Born (March 3, 1910) and educated in St John’s Wood, London, she was one of the nine children of businessman Louis Silberston and his wife Phoebe. Her grandfather had been an alderman of the City of London, and most of the family were members of the Gold and Silver Wyre Drawers, a City craft guilds.

Gertrude married Ronald Shilling, who was something in the rag trade, and with whom she had David, her only son. The family lived in London’s west end, and socialized at places like the races at Deauville.

Gertrude encouraged her son’s design sense. He was 12 when he first designed a hat for her – she wore it to Ascot in 1966, stunned the staid folk in the enclosure and made the front page of the evening papers. It was the beginning of more than 30 years of Ascot outings for the mother-and-son partnership.

“I was at St Paul’s,” said David Shilling. “And 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.

“My mother’s outfits were outrageous, but as I got older they became more glamorous and that really sowed the seeds for this revolution. It is exciting that women have the freedom now to dress how they want.”

Gertrude Shilling was often congratulated on her slender figure but she had had to struggle hard for it. As an 18-year-old debutante, she weighed 14 stone and hated being photographed. At her coming-out dance she wore a silver and white dress and described herself as looking like “an oversized fairy queen.”

The following year, she vowed to lose weight in time for a Cote d’Azur party, with the Prince of Wales and Noel Coward among the guests. In five months she lost four and a half stone. A young man, who had not seriously noticed her before, told her she looked gorgeous. To celebrate, she treated herself to a white swim suit, with stripes of red and blue stripes, at Debenham and Freebody in Wigmore Street; a matching cap made her look a little like a French revolutionary.

Gertrude was first diagnosed with breast cancer in the 1960s, but did not let it impede her appearances at Ascot. She was later the first woman to have a breast implant in Britain. She worked for charity, entertained the elderly and kept her hats in a special warehouse near in home. When all was said and worn, she had chutzpah.

“She was great fun, incredibly energetic. A gay icon before the term was even thought of. She got cancer while I was still at school and then survived 35 years after diagnosis. Amazing. Having Royal Ascot to look forward to each year helped to prolong her life, giving her that goal of getting there.”

Gertrude Shilling died on October 13, 1999.