Kennedy Oaks Day 2022: Best and worst dressed celebrities at the Birdcage at Flemington Racecourse

While the horses battled it out for a $1million prize on the track at Flemington, the real competition took place on the field as Australia’s celebrities brought their sartorial A-game on Kennedy Oaks Day. 

Traditionally known as ‘Ladies Day’, the nation’s celebrities braved the breeze in Melbourne in an array of bright and pastel colours, baffling ensembles and eye-catching lengths. 

Many nailed the racing fashion brief, but others missed the mark with bizarre asymmetrical cuts, strange colour combinations and unflattering dress lengths.

Among those was Andy Lee’s girlfriend Rebecca Harding, whose strange semi-sheer skirt, asymmetrical shirt and bustier and pastel blue headpiece hit all the wrong notes.

Her grey wool houndstooth bustier was by Fendi and retails for $3,190.

Andy Lee’s girlfriend Rebecca Harding’s strange semi-sheer dress, asymmetrical jacket and pastel blue headpiece hit all the wrong notes (pictured); joining Rebecca was the TV host Melissa Leong, whose Cinderella-inspired bejewelled ensemble was a bizarre choice

The Block star Sharon Johal also chose a garish green number that served to swamp her figure (pictured)

Jules Robinson’s grey Elle Zeitoune dress and Serena Lindeman bunny ears fascinator washed out her beautiful pale complexion (pictured), while Hannah Ferrier’s floral ensemble had a similar effect 

Joining Rebecca was Masterchef Australia judge Melissa Leong, whose Cinderella-inspired bejewelled blue ensemble fell at an equally awkward, unflattering length, and marked her second appearance in FEMAIL’s worst dressed list this week.

Melissa paired her strange sheer bling-y ensemble with burgundy accessories, and ended up with an outfit that looked mismatched.

Jules Robinson’s grey Elle Zeitoune dress and Serena Lindeman bunny ears fascinator washed out her beautiful pale complexion, while Hannah Ferrier’s floral ensemble also did nothing for the TV star. 

The Block star Sharon Johal also chose a garish green number that served to swamp her figure.

Making an appearance in both best and worst dressed was supermodel Nicole Trunfio, who first wowed in a stunning tweed pink mini suit that was a tribute to the late Chanel designer, Karl Lagerfeld, but later changed into a neon-form fitting pink outfit, complete with elbow-length gloves and a floor-length satin coat

Making an appearance in both best and worst dressed was supermodel Nicole Trunfio, who first wowed in a stunning tweed pink mini suit that was a tribute to the late Chanel designer, Karl Lagerfeld, but later changed into a neon-form fitting pink outfit, complete with elbow-length gloves and a floor-length satin coat.

Melbourne model and Josh Daicos’ girlfriend Annalise Dalins, 21, opted for a risky blue thigh-high split that was a slightly racy choice for the conservative Flemington.

The otherwise pretty dress was bizarrely paired with pearl-encrusted sheer sleeves which did nothing for the overall outfit effect.

Model Nikki Phillips narrowly missed the best dressed list with her bright orange asymmetric-sleeved Mariam Seddiq dress, which swamped her delicate figure thanks to a strange statement waist detail.

Racing royalty Kate Waterhouse was also a whisker away from best dressed, with her stunning pink and red houndstooth two-piece suit, but her choice of hat didn’t quite match.

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Melbourne model and Josh Daicos’ girlfriend Annalise Dalins opted for a blue thigh-high split that was a slightly racy choice for conservative Flemington, while Nikki Phillips narrowly missed the mark with her statement-waisted Mariam Seddiq dress

While Jamiee Belle Kennedy’s choice of Barbie-pink dress was beautiful, the combination of the plunging neckline and frou-frou sleeves was more garish than girlish (pictured); racing royalty Kate Waterhouse (pictured) narrowly missed best dressed 

The 29-year-old style icon Jamiee Belle Kennedy’s choice of bright pink dress and matching headpiece perfectly nailed the Barbie-core trend (pictured)

The newly single Olivia Molly Rogers’ outfit choice was another sartorial standout. Her pastel blue Oglia Loro Couture dress was incredibly ladylike, especially when paired with a Valentino clutch bag and Stephanie Spencer hat (pictured)

But the show stopping outfits weren’t all for the wrong reasons – with some A-listers absolutely nailing their look on the day.

Among them was the always stylish Kennedy Luxury Group creative advisor Jamiee Belle Kennedy. 

The 29-year-old style icon’s choice of bright pink dress and matching headpiece perfectly nailed the Barbie-core trend, while her accessories were well-coordinated.

The newly single Olivia Molly Rogers’ outfit choice was another sartorial standout.

Her pastel blue Oglia Loro Couture dress was incredibly ladylike, especially when paired with a Valentino clutch bag and Stephanie Spencer wide-brimmed hat.

Christian Wilkins also ensured all eyes were on him, with the son of TV star Richard Wilkins turning heads in a floral peplum dress with the word ‘God’ emblazoned across the front, along with a Matador-inspired hat and leather boots (pictured)

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Tayla Damir impressed the fashion crowd in a green slip dress and pink hat, while model and 2022 Melbourne Cup Carnival Ambassador Demi Brereton was the picture of Audrey Hepburn-inspired elegance in her powder blue dress and white gloves. 

Christian Wilkins ensured all eyes were on him, with the son of TV star Richard Wilkins turning heads in a floral peplum dress with the word ‘God’ emblazoned across the front, along with a Matador-inspired hat and leather boots.