Ahh, the Melbourne Cup. It doesn’t really matter whereabouts in Australia you are, the first Tuesday of November is an opportunity to dress up, drink champagne and have flutter at the races. The actual race itself is the richest group one race in Australia (first across the line last year, Americain, won AUD$3.3 million!) and at 3.2Km it is one of the longest. It is an Australian tradition 151 years in the making, but unlike other mid-week race meetings, Cup Day is little bit different, it’s an event targeted at women. This means two things; glamorous luncheons and high teas; and Fashions on the Field.

Now, I’ve been working at race tracks for the last four years, so here are my top tips for looking fabulous trackside.

1. Stay away from facinators. They’re cheap but more importantly, they look cheap. It looks like you’re wearing an intergalictic parasite made out of feathers and sinamay. It’s sucking your brains out through your skull. Don’t.

2. A word about cocktail dresses. Racetracks are windy places. Do yourself a favour and wear something that comes to at least your knees. Otherwise I promise that you will spend your whole day holding down the folds of your skirt. Try a tea-dress or something more suited to day-wear. Satin is best avoided as it rarely looks flattering in daylight.

3. In stilettos, walking around on the grass near the track, or inside a marquee, quickly becomes uncomfortable. Oh, and messy. I’m not saying that you should’t wear your most glamorous pair of high heels, but I would recommend wearing something without the kind of heel that is going to sink two inches into the earth with every step. Keep a pair of afterparty shoes in your bag if you’re worried.

Here are four ensembles that are unconventional, awesome and break a few of the rules.

An Ode to Apfel

This outfit pays homage to the amazing Iris Apfel, rocking electric purple, gold, and a turban all at once. Start the day with a visit to the horse enclosure, then enjoy a lively lunch with friends and a mojito or three. Dance with one or two dashing strangers and keep a record of the compliments you receive. Bonus points for wearing an amazing Egyptian styled statement necklace.

Gold Turban | Purple Kaftan | Sandals | Clutch | Feather Earrings | Statement Necklace | Sunglasses

Eastern Filly

Rethink head-wear with the gorgeous embellished vintage comb. Do your homework beforehand and choose a horse for each race. Place your bets with a bookie at the beginning of the day (and flirt to get over-odds).  Keep hydrated with fruit juices. Gossip with friends about this years Fashions on the Field winner and help yourself to tapas for lunch. Collect your winnings from the bookmaker’s stand on your way home.

Cheongsam | Floral Heels | Vintage Piano Shawl | Comb | Clutch | Armband | Earrings

Palamino in Pink

Cosy up  in this amazing Prada faux-fur and bat your lashes from underneath a pink beret. Have lunch at your favourite desert parlour before hand. Bet small change on horses with funny names and squeal with your friends when they come first! Open a bottle of  Billecart Salmon Brut Rose at three o’clock and giggle your way through the rest of the day. Bonus points for sporting a polka dot manicure.

Dress | Faux-Fur | Beret | Stockings | Shoes | Cocktail Ring | Clutch | Gloves

Tartan Bearer

Break the rules and wear trousers to the track! Have high tea at one of the marquees and then spend the rest of the day flirting with handsome strangers. Pick all your horses based on the colour or the jockey’s jersey. You manage to squeeze a pair of opera glasses into your purse, which comes  in handy for watching the big race from afar.

Trousers | Blouse | Cape | Shoes | Cloche | Gloves | Clutch

Extra Credit

How to bet with a Bookie

Melbourne Cup Trivia

The Official Melbourne Cup Website