There has been no shortage of fashion disasters over the years during the Melbourne Cup Carnival.
And 2024 certainly did not disappoint the critics.
DJ Perri Lee topped last year’s worst-dressed list, with an outfit that seemed more suited for a fairytale than the Flemington races.
The young woman, famous for her individual fashion sense, caught everyone’s attention with a vibrant pink dress. It was fitted at the waist and then flared out into many layers of soft tulle.
The middle section of her dress was see-through, revealing her midriff as she confidently ignored any dress code expectations.
The dress was completed with a matching pink purse and veil, both adorned with a bow that matched the color of her dress.
 

Another surprising fashion moment came from Brodie Ryan, formerly known as a WAG, who wore a Leo Lin dress that wasn’t very flattering.
The satin material reflected the light awkwardly and the floral details distracted the eye.
The necklace she chose seemed mismatched with the details on her hat, leaving people puzzled, and her boxy clutch didn’t fit the overall style at all.
Despite a somewhat strange hat and dress, Brodie successfully created a naturally elegant look with her simple hair and makeup.
That year, Melissa Leong continued to express her unique and unconventional fashion sense when she attended the Lexus Marquee in the Birdcage.
Okay, let’s talk about this look. The color of Viceta Wang’s dress – a really striking, burnt red – actually looked great on the TV personality. But honestly? That’s where the positives ended. While red is definitely having a moment, this particular take on the trend just didn’t quite land. It felt a little off, and the overall effect wasn’t as polished as it could have been.
The navy hat and maroon bag didn’t quite match, and her chain necklaces seemed better for a concert than for everyday wear.
The ruffled and layered details on the front of the outfit created a relaxed, intentionally mismatched, and textured look.


If there was an award for the worst outfits ever worn to the Melbourne Cup, Gabi Grecko would almost certainly win. Her outfit in 2014, worn with her then-boyfriend Geoffrey Edelsten at The Birdcage, was notoriously shocking.
The woman, previously a sex worker, wore a playful outfit – a corset and feather headdress reminiscent of a clown – after becoming involved with the businessman following his divorce from Brynne.
Everyone was stunned as the celebrity confidently walked by, showing off like they owned the place.
In 2022, Crystal Kimber quickly earned a spot on worst-dressed lists thanks to an outfit with excessive bows.
Crystal’s outfit – her dress, shoes, and headpiece – was beautiful, but there were so many details that it was difficult to appreciate any single element.
I’ll never forget when Bec Hewitt showed up at The Birdcage in 2006! She really turned heads walking in with Lleyton, her tennis star husband. It was such a glamorous moment, and everyone was talking about it!
She wore a strange top resembling a boob tube paired with white bike shorts.
The Home and Away actress made a fashion misstep at the event by wearing black and white, colors typically saved for Derby Day. She also broke the Victorian Racing Club’s rules about what people are allowed to wear.


The Virtual Reality Council (VRC) doesn’t allow certain clothing items, including short jumpsuits, tops that show the midriff, and shorts, according to their website.
Bec finished her unique look with a white jacket, black and white sandals, and a sparkly black clutch, completing the outfit despite the top not fitting perfectly.
She accessorised with a ruffled fascinator in her tightly curled hair and wore a white Dior watch.
At the 2021 races, jockey Michelle Payne wore a striking turquoise outfit. It featured a modern, ice-like headpiece and a layered halter dress that looked like something from a fancy chocolate box.
Honestly, she was stunning at first glance – that golden tan and her hair swept up so beautifully gave her an angelic look. But then, the whole outfit just…didn’t quite work. The colors were way too bright and the accessories were just so strange, it kind of ruined the effect. It was a shame, because she had so much potential!
Bec Judd, who often attends horse racing events, has had a few fashion misses over the years, even though she’s generally known for her great sense of style.
In 2009, she turned heads on the red carpet at Crown Oaks Day wearing a one-of-a-kind dress made of layered, beige tulle.
She finished the outfit with a beautiful, matching beige fascinator decorated with feathers and lace.





Meanwhile, The Biggest Loser star Tiffiny Hall wore a eccentric hat to Melbourne Cup Day in 2014.
The trainer smartly chose a simple dress to go with her very noticeable hat, but some people questioned whether the hat was a good choice.
Model Ashley Hart is famous for her bold and unusual race-day fashion, and several of her outfits are particularly noteworthy for their creativity.
At the 2014 Flemington Racecourse event, Jess Hart’s sister caused a stir with her outfit – a blue dress featuring an unusual tulip-shaped ruffle around the waist.
A year later, she appeared on the worst-dressed list again, this time wearing a brightly patterned dress with clashing accessories.
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2025-11-03 05:19