Oaks Day best dressed: Flirty, fresh and fun the winning formula

Oaks Day can present fashion lovers with a dilemma: do you lean into the tried-and-true formula of pastels and florals, or do you go for something left of centre in an attempt to shake things up? Or, perhaps, a little from column A and a little from column B?

Oaks Day 2024 - Figure 1
Photo The Sydney Morning Herald

As Cup Week draws to a close, it’s a welcome sign that the penultimate day of the carnival continues to gain fashion cred. Here were some of the best on ground.

Michelle Payne, trainer, Melbourne Cup winning jockey 2015

Winning feeling ... Michelle Payne.Credit: Penny Stephens

Dress: Vivienna LorikeetMillinery: Wendy Scully

Having accessorised her jockey silks with the Melbourne Cup trophy in 2015, it’s safe to suggest that Michelle Payne has good instincts.

“The best outfit is one that you feel comfortable in immediately,” Payne says. “I knew this dress was a winner straight away.”

Weaving her way through the Crown marquee like an embellished ice skater, Payne sported a Russian-style headband that added some formality and centimetres to the cheerful ensemble.

“I take the extra height where I can,” she says. – Damien Woolnough

Oaks Day 2024 - Figure 2
Photo The Sydney Morning Herald
Damian Hurley, director

Mum’s the word – Damian and Elizabeth Hurley arrive at Oaks Day.Credit: PENNY STEPHENS

Suit: Tanner FletcherBoots: Dior

At the risk of outshining his famous mother, Elizabeth Hurley, wearing a white lace Monique Lhuillier dress after her outing in sunflower Rebecca Vallance to Tuesday’s Cup, Damian Hurley added best-dressed male to his list of accolades, many of which revolve around his incredible bone structure.

After a brief visit to the Birdcage, the pair, guests of the Victoria Racing Club, spent Oaks Day in the Committee Room, before judging the best-dressed and best-suited finals of Fashions on the Field.

While the Hurleys were notoriously mum where interviews have been concerned this week, Damian was happy to share details of his suit, by American designer Tanner Fletcher, which added a playful spin to the gender norms of Oaks Day. – Melissa Singer

Oaks Day 2024 - Figure 3
Photo The Sydney Morning Herald
Gemma Ward, model/actor

In her flapper era … Gemma Ward at Crown.Credit: PENNY STEPHENS

Outfit: ZimmermannJewellery: PaspaleyMillinery: Ezara/JShoes/bag: Jimmy Choo

Looking like she stepped off the set of an adaptation of The Great Gatsby, model and actor Gemma Ward was ready for a good time at the Crown Marquee in a current-season Zimmermann column dress, and a lot of pearls by Paspaley, from Ward’s native Western Australia.

Asked when she feels her most feminine – because, Oaks Day – the model-actress says when she’s doing self-care, enjoying nature with her three children or dressing up. “I do a lot of self-massage with oils, and I do love an ice bath,” she confessed.

Before arriving in the Birdcage, Ward stopped past the mounting yard. Does she ride? A little, says Ward, who has walked for Prada and Alexander McQueen. “I’m trying to convince a friend of mine to buy a horse.” – Melissa Singer

Oaks Day 2024 - Figure 4
Photo The Sydney Morning Herald
Renee Brown, Jardan, creative director

Jardan creative director Renee Brown in the Landmark by Lexus marquee wearing La Double J, with Loewe sunglasses and Charles & Keith handbag.Credit: Penny Stephens

Outfit: La Double JSunglasses: LoeweHandbag: Charles & Keith

It’s a short leap from making desirable furniture to crafting a look that you’re perfectly at home wearing. Former model and Jardan creative director Renee Brown applied her domestic design skills to the racewear brief.

“It’s a day for creatives in the Lexus marquee, so I was determined to be creative with colour,” Brown says. “I’m obsessed with colour and patterns and wanted to be bright today.”

The brocade, chartreuse-yellow outfit with a blue ostrich feather trim was in the spirit of Prada. “But it’s La Double J,” Brown says. “A few people have said it’s Prada, but that’s not a bad thing, is it?” – Damien Woolnough

Oaks Day 2024 - Figure 5
Photo The Sydney Morning Herald
Emma Scodellaro, Fashions on the Field Best Dressed winner and Kalombo Ntumba, winner of Best Suited

Fashions on the Field Best Suited winner Kalombo Ntumba from Sydney (left) and Best Dressed winner Emma Scodellaro from Greendale at Flemington racecourse.Credit: PENNY STEPHENS

After 15 years as a Fashions on the Field bridesmaid, Emma Scodellaro finally walked down the Flemington runway in Dior-inspired wedding white, winning the Best Dressed category and $20,000 cash.

“It’s been a dream come true,” says Scodellaro.

The collectible’s curator is a regular entrant at racetracks around the country but the Melbourne Cup carnival win is the biggest feather in her Jill Humphries hat. “People know how much I give to this. It takes my breath away.”

Best Suited winner Kalombo Ntumba wouldn’t reveal the tailor of his chartreuse suit. “I’m going to be that guy,” says the accountant. “I’m gatekeeping, but it begins with an S.”

As for the $20,000 prize money, he says: “Interest rates are terrible. It’s going on the mortgage.” – Damien Woolnough

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