Thousands of racegoers packed Royal Randwick in Sydney and Melbourne’s Caulfield Racecourse on October 17, 2026, for two of the biggest events on Australia’s racing calendar: The Everest and the 150th running of the Caulfield Cup.
Sydney and Melbourne Rivalry Flares as Randwick Hosts The Everest
The long-running rivalry between Sydney and Melbourne took center stage at Royal Randwick as the style set turned out for TAB Everest Day. Racegoers embraced the official A Touch of Blue dress code in tailored suits and flowing gowns.
Singer and model Alli Simpson went all out in a tailored blue suit. Meanwhile, The Real Housewives of Sydney and The Traitors star Krissy Marsh radiated in a saucer hat and an off-the-shoulder white gown, accompanied by her daughter Milania Marsh, who wore a headband, clutch, and a burgundy gown.
Her mother, Krissy Marsh, added: Oh look, The Everest is taking things to new heights because we’re not Melbourne, we’re Sydney, and we actually have good weather, so it actually is good for spring.
That sunshine matched conditions down in Melbourne, where the Caulfield Cup celebrated its 150th anniversary on an unseasonably warm afternoon with large throngs of twenty-somethings descending upon the racecourse.
Fashion Rules and Faux Pas at Randwick and Caulfield
Judges and designers at both tracks laid down firm opinions on what works trackside. Kate Waterhouse served as a judge in the ATC Fashion Stakes wearing a lavender Acler dress and a Ford Millinery hat, noting that she loves seeing how everyone interprets the mix of traditional racing elegance and modern fashion.
Racing fashion is a great opportunity to have fun and experiment, but you should still feel comfortable and confident.
Kate Waterhouse
Supermodel Montana Cox looked striking at Randwick in a blood-red strapless dress featuring a sheer floor-length skirt underneath, accessorized with a coordinating pillbox hat. Fashion designer Mariam Seddiq looked effortlessly chic in a high-necked dress, accessorizing with Chanel and adding a pop of blue with a pinky ring, while offering a blunt assessment of racewear missteps. Anything that needs constant adjusting is a big no. You should be able to move comfortably without the outfit losing impact,
she said.
Down in Melbourne, Bonnie Lane leaned on maternal wisdom for her trackside style. The wife of jockey Damien Lane wore a dress featuring embellished lemons and oranges mixed with black polka dots, paired with a black Stephanie Spencer fascinator. Lane mentioned that she has established several strict style guidelines over time, though her primary principle originates from her mother.
Powerbrokers and Celebrities Mingle in the Committee Rooms
Away from the mounting yard, politicians, sporting legends, and business leaders filled the invitation-only committee room at Caulfield.
Among the prominent figures in the VIP area were Racing Victoria chief Aaron Morrison, VRC vice chairman Michael Ramsden, businessman Gerry Ryan, former Collingwood president Eddie McGuire, trainer Gai Waterhouse, former jockey Michelle Payne, award-winning actor Rachel Griffiths—fresh from the set of her new project—footy great Chris Judd, ex-jockey Tom Prebble, former MP Martin Pakula, and former Melbourne Racing Club chair John Kanga. Prolific racehorse owners Ozzie Kheir, Rupert Legh, and John O’Neill were also spotted, alongside Olivia Molly Rogers, who arrived arm-in-arm with partner Hugo Breakey.
Jason Kimberley was spotted at the track. Meanwhile, Captain Maverick delivered a winning start to the day for 3AW breakfast radio host Ross Stevenson by taking out the second race in Doomben.
Notable Fashion Standouts Across Both Racecourses
A mix of custom couture, local Australian labels, and striking tailoring drew praise from style commentators at both venues, including Olivia Molly Rogers floating through the enclosure.
| Attendee | Outfit Details | Location |
|---|---|---|
| Olivia Molly Rogers | Blush pink custom Oglia Loro Couture jacket and tulle skirt with a custom Melissa Jackson hat | Caulfield |
| Lucy Elam | Soft blue Deconduarte dress with a textured scarf, silver Bellini shoes, and a matching Novo bag | Caulfield |
| Montana Cox | Blood-red strapless dress with a sheer floor-length skirt and pillbox hat | Randwick |
Lucy Elam’s frock seemed to float in her wake as she wore a Deconduarte dress for the first day of the Spring Racing Carnival. When Elam learned the dress was by local Perth-based label Deconduarte, she knew she wanted to hire it for the occasion, stating she loved that it was a small Australian brand. Olivia Molly Rogers’ look was styled by Meggy Smith, featuring a tailored contoured jacket that juxtaposed her feminine tulle skirt and was completed with a custom Melissa Jackson hat. It feels like a modern take on traditional racewear,
Rogers said of the outfit. Other attendees included sparkly Brightonites Zana Pali and Calista Clements, who parked their podcasts and social media projects for the day to enjoy the festivities.