It’s the day that kicks off the Melbourne Cup Carnival, but just because it’s not the main event, doesn’t mean it’s short of drama.
Derby Day has attracted some of Cup Week’s most memorable looks in recent years, despite enforcing a strict black and white dress code.
It has also attracted some of the biggest stars, including Nicole Kidman who made a rare appearance in 2012, and Spice Girls icon Mel B, who was seen trackside at Flemington back in 2010.
One of the most unforgettable Derby Day moments occurred just a few years ago, when the now 36-year-old model Erin Holland was snapped suffering a wardrobe mishap inside the prestigious Birdcage.
The former Miss Universe Australia wore a custom Daniel Moore Couture gown in 2022 that featured a white top with ruffle detailing with a figure-hugging black pencil skirt.
Her outfit was quickly labelled “stunning” and “gorgeous” by fans, but Holland later came unstuck when the dress’ thigh split revealed a little more than she bargained for.
In a series of very relatable snaps, Holland – who had been styled by fashion guru Donny Galella – inadvertently flashed her undies to onlookers while moving between the invite-only marquees inside the exclusive enclosure.
Of course, wardrobe disasters can happen to anyone (we’ve all been there), but unfortunately for Holland, hers occurred in front of a team of waiting photographers.
She had the last laugh though, returning the following year in a killer ensemble that saw her hailed as the style icon of Derby Day 2023.
This time she opted for a custom white mini-dress made by Jaton Couture, styled again by Galella, that featured a statement hood while attending as a guest of Penfold’s.
The outfit was paired with a black Bulgari bag and Billini peep-toe shoes as well as black leather gloves.
“This is so hot,” one follower declared at the time, confirming Holland had recovered from her the infamous wardrobe malfunction.
“Killed it,” another agreed.
Jennifer Hawkins’ suffered her own Derby Day fashion faux pas when she turned up to the exclusive Birdcage wearing the same outfit as racing commentator Francesca Cumani.
Hawkins reportedly “brushed off the embarrassing blunder” in 2017 while trackside in Myer’s marquee.
“No biggie,” she said. “It has never happened to me before. Francesca looked so gorgeous.”
Cumani returned the compliment, stating: “I’ve always admired Jen’s style from afar, and now I’m flattered to be seen in the same dress.”
However, it was reported that by the time the TV coverage went to air, the Channel 7 host had a black blazer on over the dress.
She said in a later interview, the situation had been tricky.
“We were in the middle of coverage,” Cumani recalled, “and [someone] came up to me saying, ‘Oh my God, you’re wearing the same dress as Miss Universe.’ And I was like, ‘Great.’
“By then it was so frigging cold, and I put a big black coat on… Supposedly I was made to cover up, because Jen Hawkins didn’t like it…’ Like, whatever.”
Another star who has been the unlucky soul to suffer a wardrobe malfunction at Derby Day is former Block star Elyse Knowles, whose Flemington outfits have been labelled “risky” more than once.
In 2017, the then 25-year-old attended the first event of Cup Week wearing a white midi-dress with seemingly see-through netting as she posed outside the Lavazza Marquee.
The eye-catching design featured a large panel over Knowles’ lap that flaunted her upper thighs, and what some suspected was her undies.
It also had a similar revealing panel across her waist.
Two years later, Knowles the TV star – who has since had 3 children with fiance Josh Barker – courted more “controversy” when she “broke the Victoria Racing Club’s no bare midriffs” rule by wearing a white blazer dress with cut-outs”.
The members area dress code restrictions have caught out a few stars over the years, including Nadia Bartel who was accused of breaching the rules in 2019 with a white figure-hugging Dion Lee gown that had two cut outs on the hips.
“I did not even think about it being controversial? I just thought it was a white dress,” she told the Herald Sun at the time.
Lara Worthington also got stung by the same rule at Derby Day in 2013 when she famously wore a black two-piece to the event that featured cut outs.
The troublesome dress code has since been relaxed a few years ago.
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