How to win at the races – in the fashion stakes
Competition for the coveted title of Best Dressed Lady at Sunday's Hennessy Gold Cup is said to be more fierce than between the horses on the track
After wearing a suit all week, Margaret Connolly can't wait to get dolled up for the Hennessy Gold Cup on Sunday.
Like hundreds of other fashionistas from across the country, the Westmeath woman is throwing her hat in the ring for 'Best Dressed Lady' at Leopardstown.
But she admits not everyone will be happy to see her.
"You hear people saying: 'There's that Margaret Connolly one again!" says Margaret, a manager at Heatons in Mullingar. "I'm sure some people wish I'd just stay at home!"
Serial best dressed lady Margaret has taken top prize four times so far both at home and abroad.
"When I was 17 I went to Cheltenham with my family and saw all the women dressed up," she says. "That's where I got the inspiration to get dressed up for the local races at Kilbeggan, where I got my first big win.
"So winning best dressed at Cheltenham in 2012 was such an honour.
"I actually won best dressed at the Hennessy Gold Cup two years ago," she adds. "If you've won before, people would be saying you shouldn't win again, but that's up to the judges."
Among those hoping to give Margaret a run for her money in the style stakes on Sunday is Dawn Leadon Bolger from Wicklow.
After several photo finishes, the 26-year-old admits she has her eyes on the prize and will be taking no prisoners: "It's more competitive than the racetrack."
Film and TV student Dawn explains: "Both of my parents were jockeys, so I've been going to the races since I was born.
"I've been in the [best dressed] finals a few times, most recently at the Curragh, but I've no problem admitting that I want to win.
"It sounds crazy," she adds, "but I start planning my outfit about eight months in advance, and even do mood boards.
"On the morning of the races, it's like a military operation. I've got my outfit – a vintage Alexander McQueen suit that I got on eBay and a peacock feather hat made by my friend – and make-up for tomorrow laid out already."
If she impresses French-Canadian fashion designer Tara Jarmon and shoe designer Lucy Choi, who are judging this weekend's event, Dawn could walk away with €7,000 to blow in Harvey Nichols, as well as a bottle of Hennessy Fine de Cognac.
Cash, clothes and even a car are just some of the prizes Margaret – who splashed €350 on her most expensive winning outfit – has bagged over the years.
"The best prize I ever won was the use of an Alpha Romeo MiTo, which was taxed and insured, for a year," she says.
"I nearly cried when I had to give it back!
"I've also won a stay in the penthouse suite of the Sheraton Athlone worth €2,000 and a €5,000 voucher for Athlone Towncentre."
As runner-up, thrifty Dawn – who scours car boot sales for ladies day duds – has also gone home with goodie bags stuffed with gift vouchers for spa breaks and beauty products: "I know some people who've spent €5,000 on their outfit, but I've never spent more than €120."
Meanwhile, Carol Kennelly, from Kerry, has even managed to make a career out of getting dressed up at ladies day.
"I've always loved going to race meetings with my friends," says the award-winning milliner based in Tralee. "For me, getting dressed up for ladies day is the ultimate girly day out.
"However, I often found it difficult to find the perfect hat to compliment my outfit, so a few years back I decided to start making my own.
"Wearing a headpiece I created myself, I won best dressed lady at Listowel in 2007 and again at Galway Races the following year.
"Soon after I set up my own millinery business in 2010, Anne Marie O'Leary won best dressed at Galway Races wearing one of my designs.
"Everything just took off from there."
There is a downside to whipping the competition, warns Margaret: "When people hear you've won best dressed, they assume you've won cash.
"My house has been robbed four times in the past two years, and a fabulous €3,000 diamond necklace that I bought with one of my vouchers was stolen."
Winning isn't everything, insists four-time champion Sarah Cass from Kilkenny: "It definitely is more enjoyable when you dress up.
"You'd nearly have butterflies in your stomach going off for the day, thinking: 'Is my outfit good enough?'
"But I never go with the attitude: 'Oh, I want to win'. I also go to watch the horses and put on a couple of bets."
"Years ago, we had greyhounds and would go to the races as a family," says the 27-year-old midwife, who has won a €5,000 voucher for Newbridge Silverware and a K Club spa day for two among other prizes. "It just evolved from that.
"One day, myself and my friend said: 'Sure we'll dress up for the races in Gowran'.
"I happened to win [best dressed] and after that it was just really very addictive."
"It's the prestige more than the prize," for Dawn. "You know you're going to be in all the papers the next day.
"When you're crowned best dressed lady, it's like you're better than all the rest."
Tips on how you can be first past the post
"My biggest tip is to dress appropriately for the occasion – and the weather! You see girls going around in minskirts, skyscraper heels and fake tan: you're going to the races, not a nightclub."
"A statement hat is the key to standing out on ladies day. As I'm only 5' 4", most of the ones I go for are quite high. Make sure your hair and makeup go with the hat, and use plenty of hairpins to keep it in place!"
"Confidence and a warm smile are the perfect winning touches to any outfit, in my opinion. It shows the world that you're proud of your chosen look – no matter what anyone else thinks of it."