Black and white results in a few red faces at Derby Day

That awkward moment when you spot someone else wearing the same dress as you...

(Photo:backless formal dresses)The key to taking a fashion risk is knowing when to take one, and when to take a second look.

Monelle Mondello took one of the greatest risks at Melbourne’s Derby Day by entering Fashions on the Field for the first time, in an outfit she sourced entirely online.

Her long, striped skirt, by an Italian designer, sleeveless top and angular hat may not have had traditional racewear all over it but it won the debutante prizes worth more than $5000 in the daily competition.

“I didn’t know what to expect … it was all very last minute; my skirt only arrived in the post on Friday,” Mondello said.

Making decisions at the last minute was the fashion prescription for Derby Day, the chilliest in 40 years.

Neighbours star Olympia Valance, wearing Melbourne designer Jason Grech​, chose comfort and style over shivering at Flemington on Saturday.

“I always wear pants and thank god I wore pants because it’s freezing out there,” she said.

Valance said she learnt her lesson after freezing through the Caulfield Cup carnival, and also changed her shoes for Derby at the last minute.

“I changed to some Nine West shoes I had in my wardrobe that I know are going to be all right all day.”

Robyn Lawley​, one of the world’s best known curvy models, said she was sipping cocktails to numb the pain caused by her shoes. The Kennedy ambassador said she’s a huge fan of taking fashion risks.

“I once wore a hat that was [had a rude word on it] and it didn’t really work in my favour,” she said. “There’s a time and a place for everything. I was in New York and I was wearing it all the time around Williamsburg and Brooklyn.”

One of the fashion highlights of the day was actress Melissa George’s couture gown by Schapiarelli​, which she teamed with a Gregory Ladner​ wide-brimmed hat in the ultimate high-low move at the track.

Other celebs to make the best-dressed list included Lavazza guest and Mimco ambassador Montana Cox, in a dress with billowing white sleeves and a simple gold crown, a look favoured by The Block’s Elyse Knowles, whose Paolo Sebastian dress had a series of sheer netted panels.

Fashion blogger and TV personality Tash Sefton, wearing a polkadot shirt and a headpiece made from baby’s breath, said taking a risk requires confidence and a bit of knowledge.

“There were some girls who maybe took a risk but didn’t look in the mirror before they left,” she said.

Fashion faux pas were relatively light, although in a significant clanger, face of Myer Jennifer Hawkins and racing commentator Francesca Cumani​ were sporting the same dress