The WORST dressed celebrities at Oaks Day: Sheer horrors and awkward cuts were all the rage trackside for the ‘prettiest’ day of Spring Racing


Oaks Day is here – and while it isn’t exactly high-stakes on the race track it is in the Birdcage where A-listers are constantly under pressure to look their best.

Known as ladies’ day, the final day of the spring racing carnival at Flemington race course in Melbourne is the last chance many of the celebrities will have to put their best fashion foot forward this year.

Unfortunately for some, the higher the sartorial stakes the bigger the disaster. Here’s everyone who failed to put together the perfect outfit and landed themselves on the worst dressed list for ladies’ day this year.

Melissa Leong

Melissa Leong managed to make her make on the worst dressed list again with another awkward pop-punk race day mash up.

The 42-year-old chose an awkward bell-sleeved velvet gown with statement collar and cuff beading.

The $890 Alemais dress was paired with a pink, spotted headscarf and a $2050 mini clutch by Gucci.

She added punk-rocker inspired eyeliner and simple black heels to complete the look. 

Melissa Leong managed to make her make on the worst dressed list again with another awkward pop-punk race day mash up

Melissa Leong managed to make her make on the worst dressed list again with another awkward pop-punk race day mash up

Shaynna Blaze 

Celebrity interior designer Shaynna Blaze found herself on the worst dressed list in a wild deer themed frock.

The tulle gown featured a relaxed V-neckine, spaghetti straps and a thin black belt.

It would have been a safe bet had it not been emblazoned with deer of all shapes, sizes and colors.

The 61-year-old looked comfortable in her choice though as she smiled beneath her tiny black veil.

She wore a stylish black bag and timeless black heels for the day at the track.

Celebrity interior designer Shaynna Blaze found herself on the worst dressed list in a wild deer themed frock

Celebrity interior designer Shaynna Blaze found herself on the worst dressed list in a wild deer themed frock 

Demi Brereton 

Demi Brereton smiled comfortable at the entrance hall of the Birdcage as she swanned through for ladies’ day.

Unfortunately for the former Melbourne Cup Ambassador her choice of dress, a custom made piece by Atoir, landed her on the worst dressed list.

From the awkward wrapped scarf neckline to the sheer panels which showed off the bottom of her belly the stunning model failed to quite pull off the look.

The top of the dress almost looked like a corset, while the sides featured even more long drapes of material which confused the eye.

The blush pink Atoir bowed shoes, which would have been perfect with a simpler dress, got lost among the drama.

The 27-year-old chose a simple headband and wore her hair in a loose, low ponytail which looked beautiful.

Demi Brereton smiled comfortable at the entrance hall of the Birdcage as she swanned through for ladies' day

The dress featured awkward sheer panels

Demi Brereton smiled comfortable at the entrance hall of the Birdcage as she swanned through for ladies’ day 

Annalise Dalins

Annalise looked stunning in her super short, super structured pink dress, but unfortunately the risky outfit landed her on the worst dressed list.

It simply didn’t feel race day appropriate and did not meet the dress code requirements.

The plunging neckline, super high hemline and bare back showed off her stunning figure but stood out for all the wrong reasons at the Birdcage.

She paired the look with a hat which looked like a bizarre cross between a cowboy hat and a typical fascinator and a cute pink bag which tied in nicely with the pleated skirt.

The AFL Wag and former Miss Universe Australia model wore simple pointed Tony Bianco pumps to finish off the look.

The young woman headed to Oaks Day with her mum and was cheered on by her Instagram followers who labelled the look ‘perfection’. 

The dress simply didn't tick enough race-day boxes

Annalise looked stunning in her super short, super structured pink dress, but unfortunately the risky outfit landed her on the worst dressed list

Annalise looked stunning in her super short, super structured pink dress, but unfortunately the risky outfit landed her on the worst dressed list

Jess Gawn

AFL Wag Jessica Gawn opted for an understated look on Oaks Day, but didn’t quite pull it off.

The mother-of-two, who usually stuns on the red carpet, looked washed-out as she tried to meet the blush-pink trend of the day.

The dress, which featured an awkward knee-height tie, aged the young mum-of-two.

The tied section revealed an odd sheer piece which flowed gently to the floor. 

Jessica chose a blush headband and to wear her hair down to complete the look.

Her husband Max Gawn, a former premiership winning captain, proudly matched his wife’s outfit with a blush tie and pocket scarf. 

AFL Wag Jessica Gawn, pictured here with husband Max, opted for an understated look on Oaks Day, but didn't quite pull it off.

AFL Wag Jessica Gawn, pictured here with husband Max, opted for an understated look on Oaks Day, but didn’t quite pull it off.

Chyka Keebaugh

‘Australia’s favourite homemaker’ Chyka Keebaugh looked like a character out of the Handmaids Tale with her caped red dress.

The dress featured a strange fluoro orange strip which ran down from the waist and along the hemline earning it a key spot on the 2024 Oaks Day ‘worst of’ list.

The 55-year-old, who is typically styled brilliantly, added a ‘flight-attendant’ hat and red and gold bag which looked more suited to 1991 than the present day.

She added sky-high heels to finish the confusing look and looked thrilled with her choices as she posed for photographers at the birdcage.

'Australia's favourite homemaker' Chyka Keebaugh looked like a character out of the Handmaids Tale with her caped red dress

‘Australia’s favourite homemaker’ Chyka Keebaugh looked like a character out of the Handmaids Tale with her caped red dress

Jessie Murphy 

Jessie Murphy landed on the worst dressed list again after opting to follow the bubble skirt trend.

The stunning AFL Wag smiled at the door of the Lexus marquee in her Capellazzo couture bubble dress. 

But the proportions  of the dress seemed off and looked more ‘Jetsons’ than ‘race day’.

it wasn’t all misses for the young woman who wore stunning heels by Lana Wilkinson, a cute Bvlgary bag and vintage YSL earrings.

She wore her hair in a thick, low ponytail with the help of luscious hair extensions and topped the whole look off with a Melissa Jackson millinery hat. 

Jessie Murphy landed on the worst dressed list again after opting to follow the bubble skirt trend

Jessie Murphy landed on the worst dressed list again after opting to follow the bubble skirt trend

Rebecca Harding 

Model and entrepreneur Rebecca Harding headed straight onto the worst dressed list with her Oaks Day look.

The glamorous 34-year-old followed the wrap-scarf neckline trend which rarely works out.

She then added a handful of golden necklaces which added to the confusion.

The pale dress washed out her fine features and the full, floor-length skirt made her look much shorter than she really is.

Model and entrepreneur Rebecca Harding headed straight to the worst dressed list with her Oaks Day look

Model and entrepreneur Rebecca Harding headed straight to the worst dressed list with her Oaks Day look

Gemma Ward 

Gemma Ward  looked washed out in her Oaks Day outfit. The stunning blonde’s dress looked like it needed a good iron before the big day.

The model paired the dress with pearl necklaces and bracelets which added a touch of timeless sophistication. 

Gemma Ward looked washed out in her Oaks Day outfit

The model's dress washed her out

Gemma Ward looked washed out in her Oaks Day outfit



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