Friday 21 October 2016

What does it take to win at Ladies Day? Ireland's Best Dressed women share their style secrets

Published 26/06/2016 | 02:30

(l-r) Best dressed winners Laura Jayne Halton, Kirsty Farrell, Jennifer Wrynne and Cpt Catherine Lundon. Photo: Naomi Gaffey.
(l-r) Best dressed winners Laura Jayne Halton, Kirsty Farrell, Jennifer Wrynne and Cpt Catherine Lundon. Photo: Naomi Gaffey.
Best dressed winner Kirsty Farrell, Photo: Naomi Gaffey
Best dressed winner Jennifer Wrynne. Photo: Naomi Gaffey
Best dressed winner Laura Jayne Halton. Photo: Naomi Gaffey
​Catherine Lundon from Mullingar, Co Westmeath.

It takes more than a big hat to sway the judges on Ladies' Day. So what is the winning formula? Our reporter meets four Best Dressed ladies - who have been in 20 finals between them - to find out.

  • Go To

As the Dubai Duty Free Irish Derby gets underway at the Curragh on Saturday, the winner of the 'Most Stylish Lady' competition will receive fabulous prizes including a luxury holiday and jewellery. With so much at stake, it's no wonder that for women all over Ireland, the highlight of the annual style calendar is Ladies' Day at the races. It's a chance to don the finery and compete for amazing prizes, and with hundreds of people going all-out to impress at every racing festival, the competition to be crowned winner is fierce.

Ladies' Day also gives a massive injection to the fashion industry, with milliners, boutiques and fashion designers all striving to provide the outfits that will turn the judges' heads and see their clients romping home in first place. It's a serious business as some larger festivals offer prizes every day for the most stylish women, culminating in a major award on the final day.

For example, the winner of the 'Dundrum Town Centre Best Dressed Lady' at the Dublin Horse Show on July 21 will walk away with a prize worth €10,000, and a spectacular prize worth €10,000 will be awarded to the g Hotel & Spa's 'Best Dressed Lady' at the Galway Races on July 28.

Here, we asked four style queens who have enjoyed the thrill of being crowned Best Dressed Lady many times to share their tips for sartorial success.

Kirsty Farrell

iw IMG_8140.jpg  

Kirsty (20) is from Newry in Armagh. She works full-time in Rosie's Closet, which is co-owned by herself and her mum Rosie.

"I first went to Ladies Day at Dundalk Races in 2014, and ended up in the top 10. I had just gone for fun but really got into it after that. When we go buying for the shop, I'll see things that I love, so I order them but wouldn't have a clue where I'll be wearing them. I went to Fairyhouse in 2015 and ended up in the top three, and then I won 'Best Dressed Lady' on day one of Punchestown both in 2015 and 2016, which put me into the final. The prizes included Bollinger champagne, a €1,000 voucher for Gold Fever hair extensions and a lovely necklace.

"I have only won the overall prize once, when I won the 'Killashee Irish Tatler Style Icon' competition at the Curragh a few weeks ago in May. The prize was €2,000 for Cullen & Co jewellers and a two-night stay for 10 people at Killashee House Hotel. I picked the outfit weeks in advance when Mummy and I were buying for the shop. I spotted the dress and ordered it straight away. It was white with lace on the top, and I brought it to my milliner, Mairéad Traynor, of Millinery by Mairéad. She wanted to use the same lace because it was kind of different, so I contacted the supplier and we got it. I carried a pearl clutch, also from Mairéad, and wore pointy nude shoes.

"I was so surprised at winning and completely didn't expect it, because there was so much amazing style and my outfit was quite plain. I have all my outfits picked weeks in advance, and I obviously wouldn't spend as much as the average girl because we have the shop so I have a huge advantage there. I admire the Kardashians and their style, and my favourite outfit was probably the turquoise one I wore to Galway last year, which I got from America. It got a huge reaction on Facebook with over 20,000 likes, and lots of bloggers shared it so that was a really nice one for me.

"One of my Punchestown outfits this year was a black and white trouser suit, which was really different for me because I always wear dresses, but I thought I'd get away with it because I'm young. I'll probably enter four competitions this year, and won't be disappointed if I don't win. I just love getting done up and wearing the dresses and it's always a good laugh. It's amazing winning though, as everyone wants to take your picture and talk to you so it's crazy."

Kirsty's tips

The hat:

"You have to be confident and can't be embarrassed or uncomfortable if it's really big. It has to suit your face and hairline too."

The outfit:

"​Your dress should always be below the knee, because it's more ladylike and sophisticated and you're not going to a nightclub. The silhouette also has to suit your body."

The shoes:

"I usually always wear nude points, and think a closed toe is more sophisticated, elegant and dressy."

The secret to winning:

"I think it's down to luck, as it depends on what the judge is looking for. If you are going to take a risk, you have to feel confident, so don't go crazily different and then feel ridiculous."

Laura Jayne Halton

iw IMG_7998.jpg  

Laura Jayne (31) is from Treadstown, Co Kildare. She's a fashion designer and illustrator based in Maynooth, who has provided illustrations for Sarah Jessica Parker's fragrance campaigns and dressed nominees Fodhla Cronin O'Reilly and Nora Twomey for the Oscars.

"Last year was phenomenal for me. My client, Mary White, won the 'Kilkenny Best in Irish Design' award at the Galway Races with one of my designs. Then I entered the 'Best Dressed Lady' competition at the Dublin Horse Show in the RDS in August wearing my own black and white outfit, which is my favourite outfit to date.

"The dress had a simple silhouette, but the main attraction was the cape, which was mainly white with a Salvador Dali-inspired graphic black print all around the bottom. The hat was black with white feathers to tie the outfit together, and I wore black court shoes and a red lip.

"My sister Lisa told me to enjoy the day, whatever happened, as I had put so much work into my outfit. There were 552 entrants, and I couldn't believe it when I was called up on stage as it was my first time to enter. When my name was called for 'Best Dressed Lady,' I felt like I was actually going to faint. The prize was a €10,000 voucher for Dundrum Town Centre, which was so generous. When you run your own business, you have to make a lot of sacrifices, so it was great to be able to treat myself.

"Then in February of this year, I won the 'Powerscourt Hotel Most Stylish Lady' prize at the Irish Gold Cup Day at Leopardstown. I wore a black flared dress and a raspberry pink wool double-sided cape with a lace trim - I think I'm being called the 'Caped Crusader' at this stage. It was winter and I had the thermals on underneath so I was well prepared. I also wore a beautiful hat by milliner Aoife Kirwan from Portlaoise.

"The prize was a night in the presidential suite at Powerscourt Hotel, with spa treatments, dinner and afternoon tea and I can't wait to use it. Apart from that, the only time I have entered a competition was 10 years ago at Carton House, when my sister Jennifer and I won together and received a €1,000 shopping spree between us. The lace dress I wore was actually my grandmother's when she was in her 20s. She was crazy into style, so it rubbed off on me.

"When you win, the exposure is amazing, although you should never read the online comments. I was called Cruella de Vil, but I didn't mind as she's a legendary character who is really memorable. Coco Chanel always said to take something off when you go out the door, and I think paring it back is good. Some people do huge hats and dresses, with umbrellas and details on the shoes and bag, which can make you look more like you're in costume for a play."

Laura Jayne's tips

The hat:

"Your hat should complement your outfit, or else pick one you absolutely adore and can wear with pride, and then the outfit will follow."

The outfit:

"Choose one that suits your shape and silhouette. Don't show too much skin because it's the races, so keep it classy."

The shoes:

"Height in the shoe will lengthen the silhouette, but only do that if you can manage it. If you can't walk in the shoes, leave them at home."

The secret to winning:

"Be comfortable in your own skin. I think it's about your personality as much as your outfit, and it doesn't have to be designer. Pick one statement piece and build around it. Everything else should work in unison with that piece and not shout out so the eye doesn't know where to go."

Jennifer Wrynne

iw IMG_8081.jpg  

Jennifer is 27 and is from Mohill in Leitrim. She started her millinery business over five years ago, and has provided hats for many best-dressed winners, including herself. She recently opened a new boutique in the Powerscourt Townhouse Centre, which also sells dresses and accessories from different designers along with her own hat designs.

"I started going to Ladies Day in 2011, which was when I started my millinery business. My first race meet was Punchestown and I got a fire in my belly when I was picked as a finalist for 'Best Dressed Lady,' wearing a hat I had made myself. It was very surreal winning, as I had never gone to the races before and knew nothing about it, and I was just dressed up for the fun of it. It was a boost of confidence for my business, which was only starting off.

"I was also a finalist at Fairyhouse and Galway, and was delighted to win 'Best Dressed Lady' at the Sligo Races in 2012. I was amazed when I won 'Best Dressed Lady' on Ladies Day at Cheltenham in 2015, as the competition was huge and no one could believe that an Irish girl won over there. I didn't expect it myself at all. I won a £15,000 (€19,500) prize that was made up of a holiday, vouchers for different brands, jewellery and other lovely things.

"The outfit was by Canadian designer Greta Constantine, and I stock her designs in my new boutique. It was an emerald green silk dress and I wore raspberry, green and gold accessories. My hat that day was a raspberry disc with gold and green lace. I think that's my favourite outfit, because it was a big turning point for me with business, and it really put me on the map in the UK as well as Ireland.

"I still go to all the races and I love them, but I don't enter the competitions now because my customers take part in them. I'm happy to take a step back as I look at it from a business perspective and don't want to put a bad taste in anyone's mouth.

"I often just take a dress or hat that's left in stock at the boutique and put an outfit together at the last minute. I have a bold but girlie style, so I tend to wear bright and bold colours with clean-cut designs. I like to wear a more pared-back dress and an elaborate hat."

Jennifer's tips

The hat:

"If you're wearing a very simple dress, you should go for a big statement hat and people will talk about that. I wear my hair up to let the hat do the talking, and also sweep it to the opposite side of my head to the hat."

The outfit:

"I prefer a simple cut, which allows me to go a little crazy with the hat. You shouldn't let the hat and dress fight, as only one of them should have the wow factor."

The shoes:

"I am not a comfort person when it comes to shoes. As long as they look good, I'll suffer the pain."

The secret to winning:

"I think it's an overall well-finished outfit. There is no point in having a beautiful statement hat if your shoes aren't clean or you don't have your nails done. Be groomed and polished."

​Catherine Lundon


Catherine is from Mullingar in Westmeath and is in her early 30s. She's a captain in the Irish Defence Forces, and is currently the acting brigade transport officer responsible for transport throughout the two eastern brigades.

"I had an amateur jockey's licence when I was 17, and rode on the track in Kilbeggan, Galway and Roscommon and saw everyone dressed up for the Ladies' Days. I decided I would like to be part of that as I have style and have lots of clothes at home, so why not wear them?

"The first time I entered, I was runner up at the winter meet in Leopardstown in 2010, and then I won 'Most Stylish Lady' there in 2012, wearing a Ted Baker floral jacket and skirt, with a Fiona Mangan hat and nude shoes. I won a €5,000 prize - €2,500 was for the label FeeG and the other half was for the Ritz Carlton Hotel in Powerscourt. I was also successful at the Irish Grand National in Fairyhouse 2014, and was completely taken aback by that.

"The theme was 'All that glitters is gold,' so I had a gold Virgo's Lounge jacket that I had previously bought for a wedding in Nell's Closet in Athlone. It was priced at over €200 but I got 20pc off, and wore it with black trousers from Vila, Kurt Geiger shoe boots, a DKNY clutch bag and a faux fur collar from Ted Baker. I designed the hat myself but milliner Fiona Mangan made it. That was probably my favourite outfit. I won an €8,000 prize for Carton House, which was great. I have been a finalist five times, and when you're called, it's just a brilliant feeling and the buzz is incredible.

"When I won, the press loved it because it showed that I can be in the army, work hard, get dirty and manage weapons, but still have a sense of style and fashion. There are stereotypes around the army, but I'm here to show that it can be quite the opposite. It's important to recognise that gender does not limit us in the Irish army, and I'm as proud of my uniform as I am of my own individual style. The men I work with think it's great, and I appear to have inspired a few colleagues as some have since entered 'Most Stylish Man' competitions.

"I don't put a price on what I spend on an outfit in general, as sometimes I can be lucky and can buy something that's very reasonable, and at other times I might spend a little more to have that cutting edge or something extra. I don't go out and buy one specific thing, as it happens over time. If I see something I like, I work around it. I have also been fortunate that I have been deployed overseas with work and get to travel, so I can pick up something different that no one else would have."

Catherine's look

The hat:

"I'm a hat person, so I go for proper hats rather than little headpieces. I like milliners that push the boundaries, and I think Philip Treacy does that."

The outfit:

"The outfit should be unique to you, and should be something that makes you feel wonderful when you put it on."

The shoes:

"I love height but you should try to go for comfort. Kurt Geiger works for me because you get both height and comfort."

The secret to winning:

"Go with your own individual style, and don't follow trends. Do something unique to you and be proud of what you wear. Coco Chanel said: 'Dress shabbily and they remember the dress, dress impeccably and they remember the woman.'"

Photography by Naomi Gaffey, shoot stylist Bairbre Power

Weekend Magazine

Read More

Promoted articles

Editors Choice

Also in this section