There has been no shortage of fashion disasters over the years during the Melbourne Cup Carnival.
But the wildest look that will go down in history was worn by Gabi Grecko, who shocked onlookers in The Birdcage in 2014 alongside her then-partner Geoffrey Edelsten.
The former prostitute, who enjoyed a romance with the late businessman following his split from wife Brynne, donned a clown-inspired corset and feather headdress.
Strutting through the celebrity enclosure as proud as a peacock, jaws collectively dropped to the floors.
Geoffrey’s previous wife Brynne also garnered attention for the wrong reasons at Melbourne Cup Day in 2010.
She raised eyebrows with her extravagant feather headdress that plumed high above her.
The avian-inspired headdress was paired with an equally unusual frock that featured neon embroidery.
A year later, Brynne made another bizarre wardrobe selection by stepping out in a fluorescent pink dress with a matching floral headpiece and heels.
She was seen posing with her then-husband Geoffrey, who wore an entirely white outfit – which even included a pair of white dress shoes.
More recently, fashion mogul Pip Edwards made the worst dressed list when she attempted a cowboy-inspired look at Derby Day 2022.
Her choice was met with criticism due to an over-the-top hat that didn’t complement her ill-fitting suit.
She suffered another mishap in 2023 when she paired an all-white outfit with a trucker cap.
The P.E Nation co-founder also donned a sheer skirt over a pair of hot pants, ensuring her legs were on full display.
She topped the ensemble with an oversized blazer and a large white clutch.
That same year, Crystal Kimber made an early shot at worst dressed with an outfit featuring a few too many bows.
Crystal’s dress, shoes and headpiece were gorgeous as standalone pieces, but there were so many elements it made it hard for any one part to shine on its own.
In 2006, Bec Hewitt surprised attendees in The Birdcage by making a memorable entrance alongside her tennis star husband, Lleyton.
She wore a strange top resembling a boob tube paired with white bike shorts.
Not only did the Home and Away star seem to misinterpret the event’s theme by wearing black and white — colours traditionally reserved for Derby Day — but she also violated the Victorian Racing Club’s strict dress code.
According to the VRC’s website, clothing items such as short jumpsuits, midriff-baring garments, and shorts are not allowed.
To complete her unconventional outfit, Bec paired the ill-fitting top with a white jacket, black and white sandals and a rhinestone-studded black clutch.
She accessorised with a ruffled fascinator in her tightly curled hair and wore a white Dior watch.
In 2021, champion jockey Michelle Payne donned a monochrome turquoise ensemble that included a futuristic icicle fascinator and a tiered halterneck dress reminiscent of a chocolate box wrapper.
She looked angelic with her golden tan and elegant updo, but fell short of the mark with her garish colour theme and bizarre accessories.
MasterChef Australia’s Melissa Leong experienced a fashion fail in 2021 with her choice of accessories, as her plastic wrap did little to complement her intricate eye makeup or lime green stilettos.
Meanwhile, Bec Judd, a regular at racing carnivals, has suffered a few fashion disasters in her time, despite her well-known impeccable style.
In 2009, she made a statement on the Crown Oaks Day red carpet in a unique tulle-covered smock dress that showcased various shades of beige.
She completed the unforgettable look with a matching beige sinamay fascinator adorned with feathers and lace.
In 2011, the AFL WAG donned another unusual outfit on Melbourne Cup Day, wearing a dress that featured bib-like laying in neon yellow, a tribal-inspired necklace and a huge feathered headdress in electric blue.
Mining magnate Gina Rinehart also turned heads at Melbourne Cup Day in 2016 thanks to the dizzying amount of haberdashery trimmings that embellished her look.
From her ostrich feather handbag to the heavily-netted hatinator that obscured half her face, the glamorous businesswoman certainly didn’t hold back.
Meanwhile, The Biggest Loser star Tiffiny Hall also wore a similarly eccentric hat to Melbourne Cup Day in 2014.
While the personal trainer sensibly made sure to wear an understated frock with the eye-popping hat, many fans were left wondering whether the hat should have been worn at all.
The same could be said about several outfits worn by model Ashley Hart, who is known for her love of wacky race-day dresses and out there headpieces.
In 2014, the sister of Jess Hart made a head-turning appearance at Flemington Racecourse wearing a blue dress with a strange tulip-shaped peplum.
A year later, she once again landed on the worst dressed list after wearing a dizzingly-printed dress with an array of mismatched accessories.
Style queen Kate Waterhouse turned heads at the 2016 Melbourne Cup with her theatrical Gucci frock, which featured a dramatic pearl embellishment.
While Kate’s quirky dress was not in itself a bad sartorial selection for the stylist, the overly-embellished headpiece and chunky gold shoes saw the outfit veer squarely into OTT territory.
The Bachelorette’s Sam Frost also went for a busy look at the Melbourne Cup in 2015 after she stepped out in a boxy pinafore dress with a robot-inspired print.
Sam’s mismatched silver headband and black lace-up heels also failed to enhance her strange dress.
Rob Mills wasn’t immune from critique as he posed at the Melbourne Cup the same year, with the musical theatre performer donning a perplexing jacket emblazoned with tiny medals.
Glamorous presenter Sonia Kruger suffered a sartorial disaster in 2011 when she stepped out in a satin dress and trench coat – both in fire engine red.
The bright colour of her look failed to compliment Sonia’s bronzed complexion, while the Today Extra hosts’ mushroom-like fascinator also stood out.
