So long, headbands: The on-trend hats taking over the Melbourne Cup

When it comes to hats, Australians are a timid bunch. Even at the Melbourne Cup, where people are expected to look a little bit ridiculous, most racegoers stick with measly fascinators and embellished headbands.

But there are some recent signs of courage. The prevalence of pillbox hats and toques (brimless styles) on the international runways at Alaia, Emporio Armani and Prada have finally encouraged women to ditch tiaras and cover their crowns.

“The people who wore headbands are now the clients coming to me and ordering smaller styles,” says milliner Jill Humphries. “Headbands and fascinators were their introduction to hats. Now they want to take things further. Racewear is a great reason to push it.”

Models wear work by milliner Jill Humphries, who has found success this season with straw berets, wedges and pillboxes for the Melbourne Cup carnival.Credit: Eddie Jim

The refined pillbox style that will always be associated with Jackie Kennedy in the 1960s, during the Camelot era of US politics, is a versatile silhouette that is easier to manage than wide-brimmed boaters. In past years, photo-hungry guests resorted to floppy copies of the Jacquemus straw hat from 2018, leaving overturned champagne glasses in their wake.

“I much prefer people to draw back and embrace absolute elegance as opposed to putting something big on their head just so they will stand out,” Humphries says.

Before descending on the races at the Caulfield Cup, where content creator Rozalia Russian topped her Sportmax sleeveless dress with a compact black hat from Melissa Jackson, and at Derby Day, where model Georgia Fowler jumped on the trend, small hats dominated the northern hemisphere summer.

Lady Gaga donned a jaunty Dior beret for the Venice premiere of Joker: Folie a Deux, while Demi Moore chose a veiled pillbox for the launch of Feud: Capote vs The Swans.

“Adding a veil to a pillbox is a great way to feminise the masculine angles of some pillbox styles,” says milliner Melissa Jackson, who will judge the Lillian Frank Millinery Award as part of the Fashions on the Field competition on Cup Day.

“The style is fabulous, whether you’re having lunch indoors or squashed in a Birdcage marquee, because you’re not having to constantly readjust it,” Jackson says. “You can wear it with a jaunty tilt, to the side like an air hostess or at the back like Jackie Kennedy.”

Along with international influences, Humphries says changes to the Fashions on the Field competition, where the best-suited category is now open to women, has made smaller styles more desirable.

Lady Gaga in a beret at the Venice Film Festival; a Prada feather hat, $5300; and Demi Moore in a veiled pillbox at the premiere of Feud: Capote vs The Swans.Credit: Getty Images, Prada.

“There is something architectural about these hats, like the buildings of the ’30s and ’40s, that suits the stronger tailoring we now see women wearing,” Humphries says.

While black hats are popular, Humphries is diving deeper into the Pantone chart and championing lipstick-red toppers.

“If you have the right red, it goes with everything.”

Jackson supports the colour movement but she isn’t willing to retire big-brimmed hats from future races.

“A wide-brimmed hat can really balance out a womanly figure and generous hips,” Jackson says. “Try doing that with a pillbox.”

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