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Best Dressed at Ascot’s 2024 Winterbottom Stakes Day Fashion in the Field Parade

At Ascot’s November 30, 2024, Fashion in the Field Parade, Holly Keenan won in yellow florals and orange accessories, and Lee Madden took the men’s category in a pink suit.
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Holly Keenan won the women’s competition at Ascot’s Fashion in the Field Parade on November 30, 2024, with a yellow floral look and orange accessories. Lee Madden took the men’s category in a pink suit. The parade was held during Winterbottom Stakes Day.

Who won the 2024 Fashion in the Field Parade?

PerthNow’s recap of the November 30, 2024, event names Holly Keenan as the women’s or main competition winner. Hayley Ursich and Christine Badia were runners-up. Lee Madden won the men’s category; seven men entered.

The recap describes a day of bold colours and dozens of contestants taking the stage. It does not publish judging criteria, prize values, or formal category definitions, so the results should not be read as evidence of particular scoring rules.

What did contestants wear?

Holly Keenan’s floral look

Keenan’s winning outfit featured yellow florals, complemented by orange accessories, according to PerthNow’s event recap.

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Lee Madden’s pink suit

Madden won the men’s category in a pink suit. The recap also notes a chic trouser suit on the runway, which an unnamed Perth Racing spokesperson believed was a first for the event; it does not identify the wearer.

Charlie Smith’s hand-painted dress and fascinator

Twenty-four-year-old Charlie Smith made the top 10 in a hand-painted bridal dress and handmade fascinator. She told PerthNow she found the dress at an op shop and painted it with a spring floral theme inspired by an Oscar de la Renta dress. She said painting took more than 12 hours.

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Smith said she made the headpiece using cable ties from around her home and a narrow headband from an op shop, then used spray paint, hot glue, and beads. These are details of one entrant’s outfit—not contest requirements or evidence of a formal sustainability award.

What the event report says about fashion and making

PerthNow describes a range of approaches, from colourful styling and tailored suiting to Smith’s DIY, secondhand-sourced outfit. A Perth Racing spokesperson praised the standard of entries as “absolutely fabulous” and noted an outfit that had been recycled and recreated from a basic white transparent dress sourced at an op shop. The recap does not establish an official sustainability policy or judging category.

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Smith, described by PerthNow as a sustainable fashion advocate, said: “Being a part of an event that is so supportive of Australian fashion, and specifically the fashion community in Western Australia, is not only inspiring, but so empowering.”

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Keep the event date distinct from the 2026 race day

The parade covered here took place on November 30, 2024, at Ascot during Winterbottom Stakes Day. A separate So Perth preview, created in partnership with Perth Racing, lists the 2026 MC Equine Surfaces Winterbottom Stakes Day for November 28, 2026. That later calendar date is not the date of the 2024 fashion parade.

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