Smile, score and take no prisoners: How to judge racing’s best looks

I know what it feels like to be jockey Jamie Melham. The Melbourne Cup winner trained for a lifetime to pass the post first on Half Yours, and since rolling my eyes at my classmates’ off-white First Communion dresses at St Damian’s in Bundoora in the seventies, I have been preparing to decide the winners of the Fashions on the Field finals on Oaks Day.

It takes more than being able to assess the fashionability and fit of an outfit before someone fully enters a room to feel confident in handing over sashes for the Best Dressed and Best Suited categories, and prizes from a pool valued at $300,000.

Years of judging racewear competitions at Flemington, Randwick, Wagga Wagga and Nyngan’s surprisingly strict Duck Creek Races have helped fashion a formula that sends the man dressed like Colonel Sanders from KFC commercials to the back of the pack and has the woman unable to walk in a voluminous ballgown holding back tears in the elimination heats.

My philosophy? Smile, score and take no prisoners.

The racewear rules

1. Tap into trends
It may be the only fashion category with a direct relationship to a specific sport but most people have difficulty describing what racewear actually is.

For me, it’s more than following the codes of wearing black and white on Derby Day, bright colours for the Melbourne Cup and feminine frippery of Oaks Day. Racewear is elevated day wear that occasionally nods to tradition while engaging with the current trends.

Pay attention to the day wear part. This is for the front lawn, not the red carpet.

If you’re wearing another My Fair Lady-inspired look, be inspired by Chanel’s drop-waist silhouette, Bottega Veneta’s minimalist purpose or the deft combination of prints at Dries Van Noten. Get your head out of the history books and look at the international runway.

2. Drop the gimmicks
By the end of the competition, judges experience fashion fatigue from men carrying horse-head canes and wearing cheap patterned waistcoats, and women in 1950s vintage-inspired dresses and oversized, impractical hats.

This is racing cosplay.

Dial it down and don’t scare the horses – and the judges.

3. Don’t give Grandma a break
Older entrants in competitions deserve our respect, not our pity. I’m afraid that your Seniors Card holds no sway unless you’re demonstrating your personal style to the same level as other contestants.

4. Go shopping
Fashions on the Field is a wonderful demonstration of the skills of local dressmakers and tailors but competitors shouldn’t be afraid of stepping inside a store. Recent winners have managed to capture the sash in canny finds from ASOS, Zara, Salvos and outlet stores.

5. The wear-it-again rule
The man in the suit jacket and micro-mini skirt or woman in the stiff silver dress should be able to wear the outfit beyond the races and think about sustainability. You can also ignore Joe Cocker’s advice. You don’t need to leave your hat on.

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