The first time I was sent to cover spring racing fashion at the Melbourne Cup it was 1985, and I was fresh out of school and an unfortunate Laura Ashley phase.

I had no money. I had no clue. I had no chic.

What I did have was a brother with knee-length tennis shorts. I wore them with long white socks, white patent ballet flats with a grosgrain bow and a white trapeze top with black and gold flashes of paint over it.

I put my hair half up, half down and tied about six giant black taffeta bows in it.

Melbourne’s 1980s socialite queen Lillian Frank thought I was completely mad but oddly original and asked for a photo with me on the members’ lawn.

My other myriad outings to Flemington have been less sartorially successful and more predictable – Diane von Furstenberg shifts, a low-cut Willow dress, a rabbit fur coat that moulted on everyone – but the one constant has been my refusal to buy anything new apart from the odd thing to stick on my head.

You can’t talk Melbourne Cup fashion without mentioning Jean Shrimpton’s game-changing mini in 1965.

It’s a day occasion. It’s not black tie. Just be creative with what you have.

At a time when repurposing is all the go, I wanted to test my theory that you can shop your own wardrobe and still be a racing winner.

So The New Daily invited stylist and former Melbourne Vogue editor Anthea O’Connor to rifle my cupboard and see if I was on the right track.

O’Connor, a mother of three who runs marathons, showed up in navy wide legged and high-waisted Scanlan Theodore pants and a covetable gold 1980s-inspired top from the same label.

Oh, and a Melissa Jackson navy fedora with cream ribbon.

“I do love the challenge of this,” she said of upcycling. “Let’s mine some treasure.”

But first, O’Connor shared tips on what to do and what not to do when dressing for spring races.

She says think masculine dressing, and “don’t be too faddy. Go for what suits your body type. Put a little more money into something you know you’re going to get more wears out of rather than that random crazy panic purchase at Myer.”

Her No.1 tip for 2019 is to wear ribbon – velvet, grosgrain, even rick-rack trim – as a belt or in your hair: “Go to Spotlight and you’re basically done.”

If there’s one thing you wear to the races this year, make it ribbon. Photo: Getty

Throw away the rule book

“I’m not a big one to follow rules. It’s far more important you dress to suit your sense of self and your style. And I also think it’s more important to dress for the weather in Melbourne, especially. It’s great to have Plan A but have your back-up plan,” O’Connor says.

Remember what your mum told you

Appropriate dressing is everything, says the stylist.

You’re not off to the disco

So here’s where suits come into play.

What to wear with the suit

“Go a feature top with a fabulous pair of pants, and to me that’s a complete outfit. That’s enough,” says O’Connor.

“You’d probably add a hat, but headwear is a whole other rocky, dicey area because it can go wrong quickly. Simplicity and pared back is the name of the game there.”

Let’s take it from the top

Basically, this season you should rummage through your drawers or go to Spotlight.

Crack out the Robert Palmer suit

“Just go to the part of your wardrobe you haven’t thought about for decades and find dresses or suits you can tinker with, the boxy 1994 suit,” O’Connor says.

“The longline is fabulous, but maybe it needs just a little bit more shape through the body. Take it to the tailor and off you go. Look at what you have, your suiting, dresses you’ve had for weddings, christenings and see what can be done to refresh and reimagine them.”

But which shoe?

At this point, O’Connor points to her Chloe shoes – bought overseas on sale in 2014 – as a good blueprint.

“What I love about these shoes is the heel. A stiletto is not your friend at the track unless you’re getting a car service straight to the Lexus marquee, which is not most people.”

Now for the acid test

When shopping your own wardrobe, structure is key in whatever you choose. “Dresses are fabulous but they do need to have form and shape,” O’Connor says.

“That’s what makes a race-appropriate dress. A little bit more cover to it. It can still be sexy and fashion forward, but it needs length.”

Derby Day

O’Connor pulls out a black 1980s Covers dress – which she would team with a burgundy velvet cowboy boot, but also likes a black and white Life With Bird number, which she would pair with a black hair ribbon and gold shoe.

Melbourne Cup

O’Connor grabs a 1980s dress that was a Red Cross op shop $12 buy and recommends pairing it with either a grey suede ankle boot or the YSL gold shoe she loves, plus a “super simple” headpiece.

Oaks Day

The stylist goes straight to a vintage chiffon pleated dress.

So, giddy up. The best takeaway? “Buy well, buy one.”