When Jennifer Wrynne won the best-dressed title at Cheltenham last year in a Kelly green rental dress, a vintage shrug and one of her own hats, the headline writers had a field day with the “luck of the Irish”. Though the 26-year-old admits to Irish Country Living that she very nearly missed out on it all thanks to a pair of crippling high heels.

“My feet were actually killing me because it was the third day of racing, so myself and my mum were like: ‘Do you know what? We’ll just head home,’” says Jennifer, explaining that while a photographer at the races had taken her picture, she had not entered the best-dressed competition herself. Indeed, she had changed back into her jeans and a pair of flat boots at the hotel when a call came from a friend still at the racecourse who said that the organisers were looking for her.

“I didn’t drop my passport or my licence,” laughs Jennifer of her initial confusion. “And she was like: ‘You’re one of the top three – you better come back here quick.’”

Jumping in a taxi – and after convincing the people at the gate she had paid her £75 entrance fee already – Jennifer made it back to the racecourse with minutes to spare when she was called on stage and announced as the winner.

“I nearly died,” she says. “It was so unexpected.”

And not only did Jennifer win a prize fund worth €20,000, the resulting publicity saw her business rocket overnight.

“In order to take payments for hats, we do it on an app on the phone, and I couldn’t take any payments that day because the phone just kept ringing,” says Jennifer, explaining that within two weeks she went from working by herself to employing a full-time administrator as well as three part-time staff to help with orders.

“I don’t think anything was such a big game changer as that.”

Though then again, Jennifer has made her own luck ever since she left her job with Louis Vuitton in Dublin in 2013 to move home to Leitrim to establish her millinery business.

Going her own way

Entrepreneurship runs in her veins: her father, John Gerard Wrynne, is a beef farmer in Mohill, while her mother Mary is a curtain designer whose website features testimonials from clients including former Westlife members Kian Egan and Mark Feehily.

It was Mary who taught Jennifer to sew and inspired her interest in fashion – a passion she pursued after realising that the French and business degree she had started in Dublin was just not for her, leaving after first year to work full-time as a visual merchandiser with Louis Vuitton at Brown Thomas and study at the Grafton Academy of Design at night.

It was at this time that Jennifer started to experiment with millinery.

“It was a lot of trial and error,” she says. “Putting things together and throwing them in the bin, and starting again.”

However, when her creations started earning likes – and sales – on her Facebook page, and with one hat even winning a prize at the Melbourne Cup, Jennifer saw there could be a viable business in her hobby. Unwilling to burden herself with a loan to meet studio costs in Dublin, however, in 2013 she decided to leave her job to move home to Leitrim and open her own shop in Ballinamore aged just 23, even though some people thought she was making a big mistake.

“I was getting keys cut for the door and the guy was like: ‘Who are you? What are you doing here?’” she recalls.

“And I was like: ‘Oh, I just opened a hat shop.’ And he said, ‘A hat shop? In Ballinamore? Oh God, love, will you go back to where you came from!’”

But while the realities of running her own business soon hit home (“Somebody might be worrying about how they might afford the next dress for the night out and you’re thinking, ‘Oh my God, I’ve got rent and rates to pay,’” she laughs), Jennifer was determined to build a client base nationwide, catering primarily to the races and wedding markets, with prices on average ranging from €175 to €400 and bespoke orders and one-to-one consultations also available.

Indeed, 70% of her business is now online, driven by savvy use of social media like Facebook – she has almost 50,000 likes on her page – as well as her popular blog where she shares her personal style.

“I suppose I was the cheapest way of marketing the business,” she laughs.

“When you put a photo up on Facebook and you link it to your website, it drives traffic to your website. And if two of the customers hit on the shop section and buy a hat, then it’s worth it.”

Building her profile

Jennifer’s win at Cheltenham certainly proved that she was the best ad for her business and saw the start of a run of success throughout 2015. Not only did clients Alex Butler and Sarah Cass win awards at the Galway Races and Dublin Horse Show wearing her designs, she was also named Leitrim’s best young entrepreneur as well as winning best established business in the regional finals, with a prize of €20,000.

Jennifer has used this fund to recently launch her own boutique in Dublin’s Powerscourt Centre, with a strong focus on Irish designers and influenced by her own immaculate style. Though she admits that when it comes to working in her studio, her uniform is a lot less glamorous.

“Runners and leggings,” she laughs. “If anybody saw me, they wouldn’t be taking any style advice from me.”

Jennifer’s Style Secrets

What three makeup products could you not live without?

I recently started wearing Estée Lauder double wear foundation. It’s magical; it doesn’t budge the whole day.

My go-to lipstick is Mac in Full Fuchsia. Once it’s put on, it lasts for the day. I top it up from time to time with lip gloss, but the colour pigment remains. I have been using Diorshow mascara for years now. It lengthens your lashes, stays all day and is waterproof; most important for Irish weather!

Apart from your own boutique, name three of your favourite go-to shops?

Kabuki Boutique, Carrick-on-Shannon, Co Leitrim;

My Sister’s Closet, Dungannon, Co Tyrone; and Serendipity Boutique, Kilkenny.

Name one thing you always have in your handbag?

I would never leave the house without a little sewing kit. I always have a needle, thread and tiny scissors in my handbag. I have rescued ladies in the toilets on many occasions from zips busting to hems falling.

What haircare products work best for an event?

For an up-style where you need a firm hold, I use Redken Pure Force fixing spray and Redken Quick Tease finishing spray.

For a down-style, L’Oréal Elnett hairspray is great for a light hold, as you can brush the hair through, without that sticky feeling. For a blow dry, elixir oil leaves the hair smooth and frizz free.

Finally, any secret to staying comfy in high heels on a long day?

The sensible thing to say here would be to wear comfortable low-heeled shoes but I’m not sure if that will ever happen. A great tip I once received was to put Voltarol (for muscle pain) on your feet before you go out. It keeps them cool throughout the day, preventing swelling, which in turn prevents pain. It’s important to never take your shoes off if they are hurting you, unless you’re taking them off for the day. It’s impossible to get your foot back in and feeling normal again.