Crown Oaks Day may not stop the nation, but don’t be fooled. The style stakes remain sky-high.
Traditionally known as Ladies’ Day, the third outing on the Melbourne Cup Carnival calendar is where Flemington turns soft, pretty, pastel, and somewhat daring.
After the black-and-white glamour of Derby Day and the bold spectacle of Cup Day, Oaks Day is all about florals, sugar-spun hues and a touch of feminine flair, at least, in theory.
Because while the dress code may be lighter and the vibe more playful, the pressure in the Birdcage certainly isn’t.
This was the last big chance of the season for celebrities, influencers and racing regulars to deliver a look worth talking about, whether for the right reasons or the wrong ones.
And as always, with high style comes high risk.
There were elegant hits from the likes of AFL WAG Brit Selwood and Miss Universe Australia Moraya Wilson gracing Flemington, but there were also the inevitable fashion misfires.
Plus a famous housewife that jetted into Australia to be the celebrity guest on the day with her daring backless frock setting the bar very high.
The Real Housewives of Beverly Hills star Dorit Kemsley was the star overseas guest at Oaks Day. Although it was her Melbourne Cup Carnival debut, she absolutely understood the race-day glam brief
The reality star brought high glamour with her daring two-toned backless frock, paired with elbow length gloves, giant platform heels and a wide statement feather-adorned hat
Making her Flemington debut as a Crown Ambassador, Real Housewives of Beverly Hills star Dorit Kemsley swept into Oaks Day with pure trackside glamour.
She wore a flowing, colour-blocked halterneck gown in soft lilac, the fabric trailing elegantly down her back and finished with a delicate rose detail at the waist.
The backless silhouette was the real showstopper, balanced perfectly with sleek black evening gloves, a satin train and towering pumps.
And to top it all off, a dramatic, feathered wide-brim hat that sealed the look as racewear perfection.
With style like this, Dorit has a solid chance of scoring a return invite next year.
AFL WAG Brit Selwood was also a trackside standout.
Sleek and statuesque in a head-to-head white outfit, the wife of former footy player Joel Selwood was a dream in this monochrome ensemble. (Even if it had more Derby Day dress code vibes than Oaks Day.)
The sharp structural elements around the shoulders and hips paired with a big circular hat was a risk – but one that paid off beautifully for Brit.
AFL WAG Brit Selwood was sleek and statuesque in a head-to-head white outfit. The sharp and structural floor-length dress fit her like a glove, making for an overall chic look
Demure pillbox hats were the headwear trend we never saw coming at 2025 Oaks Day. The statement headpiece was seen on (from L-R) Bella Henry, Jessie Murphy and Eden Kannourakis
Model Lindy Klim wore a striking floral dress that was confident, playful and perfect for the more relaxed Oaks day dress code
Miss Universe Australia Moraya Wilson certainly ruffled our feathers in her Alin Le’Kal mini and one of the most show-stopping headpieces of the day
Meanwhile, a very particular statement style of headwear piece was a popular and repeated choice among the fashion set.
The demure pillbox hat proved to be a popular choice, as seen on Jessie Murphy, Bella Henry and Eden Kannourakis.
Despite fashion critics questioning whether the headwear has a little bit of plane stewardess energy, its recurrence at Oaks Day as well as Melbourne Cup days earlier suggests this probably isn’t the last we’ve seen of this emerging trend.
Meanwhile, perennial best dressed lister Lindy Klim was a spring carnival dream wearing a floral dress that was confident, playful and yet rode that casual line that is so particular to Oaks Day.
Having a very butter-yellow moment were former AFL WAG Brodie Ryan (left) and model Mia Fevola (right). While most were opting for headbands, Mia has embraced the veil
Ruby Brownless got the pretty pastel memo and aced the brief in exaggerated pleats
Paired with a black turban-style headpiece, a dark green purse, drop earrings and black pumps, this level of mix and matching is one only a seasoned fashionista would dare attempt – and be able to pull off so well.
Miss Universe Australia Moraya Wilson certainly ruffled our feathers in her Alin Le’Kal mini, silver accessories and one of the most show-stopping headpieces of the day. Kudos to her Melbourne-based stylist Alicia Marshall.
Having a very butter-yellow moment were former AFL WAG Brodie Ryan and model Mia Fevola. While most were opting for headbands, Mia embraced the veil.
Meanwhile, Ruby Brownless got the pretty pastel memo and aced the brief in exaggerated pleats.
Better luck next year
Some eyebrow furrowing fashion choices meant that not everyone had a winning day out at the races.
Racing royalty Kate Waterhouse had been amongst our top picks for best dressed on Cup Day.
Kate Waterhouse was amongst our best dressed on Cup Day. But just a few days later, her Oaks Day outfit left us perplexed
Tessa James’ strapless sequined blue dress was undoubtedly pretty, but lacked the wow-factor of a racewear look
But in an unexpected about face, Kate was near unrecognisable in an ensemble that looked a little awkward.
The tone felt, dress length and burlesque-red ribbon details all felt a little off. And the less said about that bustle tail, the better.
Former Neighbours star Tessa James‘ powder-blue ensemble also proved that even sequins can sometimes fall flat.
The strapless two-piece shimmered under the lights, but sadly lacked any spark of excitement for a day that’s full of it.
Between the safe silhouette, muted colour and minimal styling, the whole look felt more bridesmaid than race-day glamour. Pretty? Yes. Memorable, unfortunately not.
Another puzzling outfit choice was made by make-up artist Jade Kisnorbo. Perhaps the usually glamorous Melbournite was struggling to get out of bed – and instead just decided it would be simpler to take the bedsheets with her!
Jokes aside, the triple-layered drapery swallowed her frame and pooled around her feet. Between the overextended sleeves, floor-length folds and stark accessories, it was a reminder that sometimes less is more.
Speaking of oversized, the theoretical description of Alli Simpson’s gloriously oversized burgundy suits sounds high fashion – and a definite pushing of the boundary.
Jade Kisnorbo’s dramatic, draped gown drowned her frame (left), offering a reminder that less can be more. Meanwhile, Alli Simpson’s oversized burgundy suit also tipped past fashion-forward and into costume territory
Rozalia Russian experimented with a different style of races headwear
The Daily Mail style jury was out on the gorgeous Jessie Murphy
But execution-wise? Sadly, it simply looked like Cody Simpson’s baby sister had pulled something out of a much more portly uncle’s closet. Points for trying something different though – and bet it was comfier to wear than the standard fitted frock.
Although races season is an opportunity to dabble with infrequently worn headwear, Rozalia Russian’s choice was not favourite.
Channelling rap stars, the head piece in a lace matching the frock looked straight out of a music video, or a gypsy’s wardrobe.
It’s such a shame as everything else about this mint green look was on the money. So close.
Melissa Leong turned heads at Lexus arrivals with a quirky fascinator, though her silky look felt more pyjamas than party. While Sylvia Jeffreys’ pink frock and rhinestone veil tipped from glamorous to pantomime princess
However one look that divided opinions at Daily Mail Fashion HQ was the always gorgeous Jessie Murphy.
On the one hand, the lilac lace dress left little to the imagination, channelling more lingerie than luncheon. The overall effect felt more ‘boudoir at brunch’ than birdcage glamour.
But then, the structured pillbox hat with matching white heels and clutch brought it all back together. And as per usual, her flowing blonde locks and make-up was flawless.
Melissa Leong showed off her very quirky sense of style as she stepped out at the Lexus arrivals. Although her Stephen Jones millinery fascinator was a fun pop, the silky ensemble looked too much like a pyjama set to us.
Sylvia Jeffreys’ pink frock came with a sparkling collar and a rhinestone-dotted face veil to match, but the combination tipped from polished to a touch pantomime princess. A little less sparkle would have gone a long way.
Oaks Day certainly was a glorious display of fashion highs, eyebrow-raising lows, and everything in between.
Whether they nailed the brief or left us scratching our heads, one thing’s for sure, the style stakes at Flemington were anything but boring.
