A lesson in elegance: The Caulfield Cup fashion winners

October 17, 2026 — 4:55pmThe Caulfield Cup is celebrating a momentous 150 years in 2026, but you wouldn’t know it looking at the crowds.Large throngs of twenty-somethings descended upon the racecourse on what was an unseasonably warm Melbourne day. Many were dressed to the nines: some in corseted tulle gowns that looked borrowed from a recent school formal, others in dresses that came dangerously close to unwanted exposure.But the old hats knew what they were doing. Olivia Molly Rogers was the picture of sophisticated elegance, Lucy Elam glowed in her sweet yet distinct blue dress while Bonnie Lane nailed elevated whimsy.Here were the big fashion winners at the 2026 Caulfield Cup.Olivia Molly RogersOlivia Molly Rogers in a custom Oglia Loro Couture outfit at the Caulfield Cup.PENNY STEPHENSOlivia Molly Rogers’ elegant blush pink custom look by local atelier Oglia Loro Couture was a welcome sight in the stands. The tailored contoured jacket 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 look, styled by Meggy Smith.Lucy ElamLucy Elam in a Deconduarte dress at the Caulfield Cup for the first day of the Spring Racing Carnival.Penny StephensLucy Elam’s frock seemed to float in her wake. Her soft blue dress featured a textured scarf that draped around her neck and fell across her waist elegantly. Paired with silver Bellini shoes and a matching Novo bag, it was a distinctly sweet look.When Elam learnt that the dress was by local Perth-based label Deconduarte she knew she wanted to hire it for the occasion: “I loved that it was a small Australian brand. Their pieces are handmade, so I made it my mission to get this dress.”Rebekah PattersonRebekah Patterson in the Beverly at the Caulfield Cup.PENNY STEPHENSSome people come to the races just to enjoy themselves, others mean business. Publicist Rebekah Patterson sits in the latter camp, but that doesn’t mean she can’t look chic at work.Wearing a sleek Eliya the Label dress that fit her like a glove, paired with a Ford Millinery headband, Dolce Firmi shoes and Chanel handbag, the South Yarra resident was poised to make all the right style statements.Delainey MaryDelainey Mary at the Caulfield Cup.Penny StephensDelainey Mary prompted a double-take as she made her way through Caulfield, that’s how striking her delicate headpiece was in person.The jewelled piece by Ezara/J Millinery is a great example of style that doesn’t need to shout to be heard. Worn with her simple baby pink Forever New dress, she’s a testament that you don’t need to break the bank to make a statement either.Bonnie LaneBonnie Lane wearing a Leo Lin dress and Stephanie Spencer headwear at the Caulfield Cup.Penny StephensBonnie Lane hit all the right notes in her Leo Lin Boat Neck mini dress. Featuring embellished lemons and oranges mixed with black polka dots, the dress is whimsical without being kitsch. Her black Stephanie Spencer fascinator gave a distinguished edge to the look.The stay-at-home mum and wife to jockey Damien Lane said she’s developed a few firm fashion codes over the years, but her main rule is borrowed from her mum. “If the dress is above the knee, you’ve got to be covered at the top.”“Race wear should be elegant and not party wear,” Lane says.Here are all the Caulfield Cup looks you need to see: Lisa De Sanctis wearing Revolve and a Zara hat in the Beverly at the Caulfield Cup.PENNY STEPHENSDanielle Collis and husband Cameron. She’s wearing a dress by Tohja, millinery by Velvet Hammer, bag by Olga Berg, shoes by Nine West in the Beverly at the Caulfield Cup. PENNY STEPHENSAdelle Petropoulos outside the Beverly at the Caulfield Cup.PENNY STEPHENSDemi Brereton dons the French Riviera look at the Caulfield Cup.Penny StephensDemi Brereton and Meggy Smith arriving at the Caulfield Cup. PENNY STEPHENSAlexander Merrett and Zach Merrett at the Caulfield Cup.PENNY STEPHENSZana Pali (left) and Calista Clements at Caulfield.Penny StephensMake the most of your health, relationships, fitness and nutrition with our Live Well newsletter. Get it in your inbox every Monday.From our partners