Who are the queens (and kings) of Best Dressed? What are the judges' essential elements? How can you use it to boost your career? And just HOW MUCH can you win?

Published: 01:46, 1 August 2026 | Updated: 01:46, 1 August 2026 Best Dressed competitions are now big business. While these glittering occasions are promoted as celebrating individuality, elegance and the power of personal style, the motivation for many contestants is not just the kudos of being anointed a style icon, but the highly lucrative prizes too. Top-tier race meetings and gatherings like the Gallagher Dublin Horse Show and the Galway Races offer amazing cash prizes of €10,000, so competition is intense. While it may be all style and smiles for the assembled media and judges, behind the scenes the generous prizes must lead to strong emotions if not occasional antagonism. Huge time and effort is involved in catching the judges’ eyes to win because participating in Best Dressed events is not only a social outing but a way to boost your bank balance or win a luxury trip with accommodation, flights, meals, champagne and spa treatments included. These lavish prizes for the most stylish attendees now challenge the equestrian events as the focus of attention. Stylist and MC Marietta Doran has previously referred to them as ‘like a competition within a competition’. Certainly, they drive major footfall within the racing calendar and help to guarantee a strong attendance. Almost every successful race meeting boasts a competition for the most stylish racegoers, with men regularly participating too. Frequently there are weeks of planning involved with the clothes, hats, accessories and grooming deliberated over and co-ordinated with military precision. Some contestants will bring multiple outfits, only deciding on which to wear at the last moment having scouted out the competition. So lucrative are these occasions that there is a core group of women who travel the circuit attending multiple race meetings annually. Motoring hundreds of miles in pursuit of a win, their motivation is often monetary, although they will never admit so openly. Winning can also be valuable in other ways, as success boosts a winner’s profile and potentially adds thousands of social media followers overnight. Previous winners of Best Dressed events include Lisa McGowan of Lisa’s Lust List, who won at the Galway Races in 2016 and parlayed her victory into a successful career as an influencer with numerous brand affiliations. Many aspiring designers and milliners still attend Best Dressed events to promote their careers by wearing their own creations. Maya Grisham accessory designer Kimberley Tino was a runner- up recently at the Dubai Duty Free Irish Derby, sporting her own Irish harp clutch bag. Faith Amond, 72, from Carlow remains Ireland’s most successful Best Dressed diva, with wins at more than 50 events. Her first was at Leopardstown over 40 years ago and she won a Range Rover Evoque at Aintree in 2017. She is the doyenne of raceday glamour but there are others hot on her heels. Here we review recent winners at Irish Best Dressed events and the lavish prizes secured by their ensembles. Jeanette Kelly wore a blush pink dress and cape by Ukrainian designer Malva Flores Dubai Duty Free Irish Derby 2026 Jeanette Kelly from Wexford won the coveted Dubai Duty Free Best Dressed at the Irish Derby at The Curragh as per judges including Vogue Williams. Her look incorporated a blush pink dress co-ordinated with a dramatic ruffled cape by Ukrainian designer Malva Flores, a headpiece by Laura Hanlon and bag and shoes from Next. She had foregone a holiday in Portugal to attend, but her spectacular win provided consolation as it included return flights for two to Dubai, five nights at the luxurious Creekside Hotel, and €1,000 spending money to indulge herself at the airport retailer. Róisín Logan with judge Marietta Doran at Gowran Races Gowran Races Best Dressed was snapped up by Róisín Logan, a palliative care nurse whose working life is spent in practical navy scrubs. In contrast, her winning outfit – pictured beside judge Marietta Doran – featured a vivid orange and pink dress with a dramatic floral corsage on the bodice, a headpiece by Hats By Caroline, pink Lodi shoes and a lip-shaped clutch bag sourced on Vinted. The dopamine-drenched outfit scored Róisín a two-night stay and evening meal at Lyrath Estate, a €1,000 gift card to MacDonagh Junction, Kilkenny, and a courtesy car for the weekend. Joann Murphy won the title at Listowel Races last September Listowel Races Harvest Festival 2025 Listowel Races are one of the oldest racing events on the Irish calendar. This year’s event won’t happen until September but in 2025, Joann Murphy from Kilgarvan won the McElligot Kia’s Best Dressed in a stylish all-white Celia B trouser suit and a Carol Kennelly headpiece paired with black and white striped shoes and co-ordinating bag. She won an all expenses trip for two to New York, with accommodation at the iconic Fitzpatrick Hotel in Manhattan. Joyce Silva was the worthy winner at Kilbeggan Races 2026 The worthy winner at Kilbeggan Races in July was Joyce Silva, a professional pastry chef who sported a self-made hat, a Coast dress, Zara shoes, second-hand Christian Dior earrings and a bag found on Vinted. Her incredible prize package, worth €4,000, included €3,000 cash, a three-course meal for two at The Old House Restaurant, Annebrook House Hotel, jewellery from Choko Jewellery, a voucher from Clypso Hair Salon, a bouquet from Theresa Nixon Florist, a luxury hamper from Mullingar Pharmacy and a bottle of Prosecco from Wines Direct Mullingar. Her vintage look was ladylike and elegant, and she wore it well.   Lisa Walsh wore a dress by Australian label Only One Ashley Galway is one of the most prestigious and therefore most competitive Best Dressed events in the racing calendar. This week the winner of the Ella & Jo Best Dressed Lady Competition was Lisa Walsh, an accountant from Dunboyne, Co Meath. Her successful look consisted of a check fit-and-flare dress by Australian label Only One Ashley paired with a Fiona Rafter hat, ladylike black gloves, a neat black box bag and bright orange shoes. Her cash prize of €10,000 will no doubt be wisely used thanks to Lisa’s profession. Nadine King won Best Dressed at the 2025 Dublin Horse Show Gallagher Dublin Horse Show 2025 The Gallagher Dublin Horse Show returns with the Best Dressed event sponsored by Poretti next Thursday, with a huge cash prize of €10,000. Last year’s victor was Nadine King from Donnybrook, who dazzled judges with her retro Pride and Prejudice-style look. The feminine outfit was styled from a dress by Agua Bendita (a Columbian sustainable clothing brand), a hat from AnedeCoco, earrings by One Dame Lane, a choker by Costume, bag by Loewe and shoes by Zara. She pulled it all together with an easy elegance to look pretty as a picture. If you would like to emulate her, then registration for Best Dressed 2026 is now open at dublinhorseshow.com. Tariq Anwar scooped The K Club's Most Stylish Racegoer at the Dubai Duty Free Irish Derby K Club’s Most Stylish Racegoer 2026 Increasingly events welcome men for their Best Dressed competitions and one such dandy, Tariq Anwar, scooped the K Club’s Most Stylish Racegoer at the Dubai Duty Free Irish Derby in June. His dapper look included a 100 per cent Irish linen pink bespoke suit, a shirt from Reiss, a striped vintage tie by Polo Ralph Lauren, a hat by Kennedy and McSharry, shoes by Marks & Spencer and sunglasses by H&M. The theme was 1950s pastels, which Tariq channelled into an outfit with hints of The Great Gatsby. The Ballsbridge resident’s prize was a three-night break for two at The K Club, with award-winning dining and exclusive estate experiences. Oniesa Owens wore a Ter et Bantine coat and top with trousers by Roisin Linnane Longford woman Oniesa Owens won the Punchestown Bollinger Best Dressed in April with her striking navy Ter et Bantine shredded-effect coat and top from Fabiani in Longford, paired with navy barrel-leg trousers by Roisin Linnane, a hat by Wendy Louise, red Alai heart heels and a classic quilted Chanel bag. Her prize was an exclusive ‘money can’t buy trip’ for two to the Bollinger Estate with flights, five-star hotel accommodation, Michelin dining and a case of Bollinger. Sorry we are not currently accepting comments on this article.