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Melbourne Cup

Opinion

Smile, score and take no prisoners: How to judge racing’s best looks

Damien Woolnough Fashion editor November 5, 2025 — 10.40am

I know what it feels like to be jockey Jamie Melham . The Melbourne Cup winner trained for a lifetime to pass the post first on Half Yours , and since rolling my eyes at my classmates’ off-white First Communion dresses at St Damian’s in Bundoora in the seventies, I have been preparing to decide the winners of the Fashions on the Field finals on Oaks Day.

It takes more than being able to assess the fashionability and fit of an outfit before someone fully enters a room to feel confident in handing over sashes for the Best Dressed and Best Suited categories, and prizes from a pool valued at $300,000.

Years of

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