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The key to a winning fashion formula for Melbourne Cup

Sydney Morning Herald (SMH) •
November 02, 2026 • 08:00 AM
• By Courtney Thompson
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Insiders share the one big rule for style success at Flemington.

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In a country where the default style setting is laid-back and effortless, occasions like the Melbourne Cup offer a rare opportunity to lean in to excess and dress a little over the top.

But with great power comes great responsibility, and racegoers can sometimes end up looking more like Effie Trinket than Zara Tindall with their extravagant looks.

It’s with this in mind that Camilla Freeman-Topper always advises restraint with one’s sartorial approach to Cup Day dressing.

“Avoid doing too much. Too many competing elements can take away from the look,” says Freeman-Topper, co-founder and creative director of Camilla and Marc.

“You don’t need to make every element of your outfit a statement. Choose one hero piece and let it lead, whether that’s a dress, blazer, colour or headwear. Prioritise fit – the most memorable looks are usually the best tailored and feel effortless not the most elaborate.”

Freeman-Topper adds that a failsafe option for the occasion is anything that champions sculptural tailoring.

“It’s an elevated take on traditional dressing, with shape and proportion that make it interesting,” she says.

“You want to look considered and polished, without feeling overly styled.”

Some of Michelle Greene’s earliest memories are of having Melbourne Cup celebrations at school and has been attending since her mid-20s.

With the insight of many years’ experience, the Jaggad co-founder and guest of G.H. Mumm says key to a winning fashion formula is sticking to what you know.

“It’s really important just to stay true to yourself and not to overthink it,” explains Greene, who’s chosen a vibrant red Jacquemus dress and leopard print pillbox hat by Millinery Jill for her Cup Day look.

“I always style my own outfits, and it’s when you feel confident that you feel great.”

As for the gentlemen, Patrick Johnson warns that slimmer does not equate with more stylish.

“It can work for some but not the majority,” says Johnson, tailor and founder of P. Johnson, who adds that another common mistake is treating it like a costume rather than clothing.

“Most men typically look a little stronger with less information: purer, simpler outfits, using beautiful fabrics.”

And if you’ve left your outfit to the last minute, Freeman-Topper directs people to their own wardrobes.

“Go back to the pieces you know you feel great and comfortable in,” she advises.

“A well-cut dress or a strong tailored look is always a good starting point. Choose one piece that does the work for you, then keep the accessories considered and simple.”

At the end of the day, Greene believes there’s more to admire in people experimenting with fashion.

“A lot of people say they put on a persona when they wear their outfit,” Greene says. “And it’s great they’re confident in themselves enough to do that and make a bit of a statement.”

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