It's a question that regularly leaves Fashions on the Field aficionado Richard Luton perplexed.
The real estate mogul and fashion devotee must have one of Canberra's most opulent and expensive wardrobes, lined with luxury brands and rainbows of colour.
And suits. Lots of suits.
"This one I had made in Singapore by my tailor, especially for Derby Day," Mr Luton said, of the houndstooth ensemble he was sporting for an exclusive peek into his closet.
"I'm wearing it with a pink rose today, because that's the flower for the Black Opal Stakes."
Ahead of Stakes Day on Sunday, Mr Luton is lamenting the woeful state of men's fashion at the races.
"I think now that racing has become more popular, almost like a football match. People don't get dressed up. But I think there is still a need for people to look good," he said.
"I think men just need advice, there's plenty of places that can help you out and it doesn't have to be gay or anything, it can just be a nice suit, a nice tie."
In other words, it's time to leave the chinos at home.
The rules regarding men's and women's race outfits have relaxed in the past few years, with men now controversially allowed to wear shorts at the Melbourne Cup.
Mr Luton himself appeared at Flemington last year in a nifty jacket-and-matching-shorts combination.
But he wouldn't dream of wearing the same get-up in Canberra: rules are rules.
"If they didn't allow it, I wouldn't wear it; they wouldn't let me in!" he said.
"And I've got a lot to choose from as far as conservative and colourful suits go."
While the dress code has been relaxed, style educator Frankie Droulias says it doesn't excuse the wave of blue shirts and chinos among the male punters on the track,
"I feel like we need to go back to when the rules were applied: men were always in a three-piece suit, a nice tie, a hat, an umbrella is a nice touch," Ms Droulias said.
"I feel like in the past we've relaxed a bit on these rules and we haven't seen as many put-together outfits."
But tell that the constant parade of blokes in safe, conservative ensembles that wouldn't be out of place at a city office.
She's not the only one disappointed in the lacklustre efforts of male racegoers; Fashions in the Field judge Nick Risteski sees wasted opportunities every year at the Canberra Cup.
He believes men often want to make more risky outfit choices but are limited by gender stereotypes.
"Fashion in general, whether you're male or female, is an expression of your personality," he said.
"Seeing the current state of men's choices, it's a real mixed bag, and unfortunately it's the minority that will go out and really express themselves with some good gear.
"On race day, you always go to back a horse, but you've got to back yourself as well."
For Mr Risteski, that means wearing a pink and white linen suit he described as a take on "White Chocolate Raspberry Swirl".
On dressing for this Sunday's event, Ms Droulias says it's out with the beige pants and chambray shirts, and in with the autumnal hues.
She recommends trying a bit of colour or a clash of prints to make a more interesting ensemble.
Different fabrics and textures can also lend some pizzazz to a race-day outfit.
And the shoes tie it all together.
"The shoe always matters! It can make or break a man's outfit, and I always say you can tell a lot about a man by his shoes," she said.
- Black Opal and The Canberra Times Fashions on the Field is at Thoroughbred Park on March 10. For more information or tickets go to thoroughbredpark.com.au.
