Dubai-it: From Ireland to Dubai, how a passion for tailoring turned this expat into an entrepreneur

Dubai: He remembers being shy, as a young boy in school. But Irish expat Stephen Conroy still remembers the effort he – as well as his mum – put into ironing his school uniform. “I was always just very interested in looking good. It’s not really about ‘standing out’ as much as it is about just looking well and feeling good,” Conroy told Emirates 24|7. Today, he runs an Irish tailoring shop in Dubai, the only one in the region, according to him. But his journey with tailoring started many years earlier, as a college student in Dublin. “I was still in college when I took a part-time job at a menswear store in Dublin and I really fell in love with the process and how people felt when they would look at themselves in the mirror, wearing a well-tailored suit,” he said. He started working more closely in the ‘made-to-measure’ section of the store, where even though the prices of suits were double, and people did not always seem keen on spending more on bespoke tailoring, Conroy was able to connect with clients, sharing his passion for good tailoring. “I was the record salesman there,” he says with pride. After spending a few years at the menswear store, he was laid off during the pandemic. With most places shut down, he fell back on his other passion – cycling. “For about six to nine months, I was just a professional cyclist in Ireland, cycling for four to five hours every day, and racing every week, non-stop for nine months, with some of the best cyclists in the country,” he said. But despite the tight schedule of cycling, he was still on the hunt for a job. Then, one day, he saw a message on his social media feed. “It was from Emirates airlines, with a message saying, ‘We’re open for business’,” he said. This was a time when almost everything around him had slowed down to a grinding halt, so Conroy decided to pack his bags and go to the one place that was still open. The best-dressed agent In September 2020, Conroy landed in Dubai, and began working as a real estate agent. Even though it wasn’t a field he had particular interest in, his background in tailoring helped with the presentability aspect of the job. “I was always dressed 10 out of 10. Anyone I met – whether my colleagues or my clients – would mention how well-dressed I was because I had brought the suits from my country,” he said. But while the real estate job gave him the proverbial foot in the door in Dubai, his heart was still in the world of tailoring. So, a year after landing in Dubai, he reached out to a tailoring house in Business Bay, after seeing a video on social media. “I just messaged them on their social media account, asking them if I could come in for a talk. I told them how passionate I was about tailoring and had five years of experience in Ireland,” he said. The love for tailoring, once again, spoke louder than all else, and Conroy got himself a job as a sales advisor. But with the tailoring shop a relatively small operation, that also meant he had to cover other aspects of the business, like managing the workshop or handle back-end operations. The experience was immersive, and Conroy was finally back doing what he loved the most. He fell back on the client base he had built working in real estate and even began actively posting online as ‘The Dubai Tailor’, commenting on the art of traditional tailoring and why the little details made all the difference between a well-tailored suit versus an ill-fitting one. “I think putting in the effort to be well-dressed also has so much to do with respect. I was always really passionate about not leaving any aspect of my personal brand on the table – I have always paid attention to the little things, even when I was working as a real estate agent. I would be on time, I would dress well, learn about the area I was selling in … it’s all part of being respectful,” he said. Then there is the tradition of tailoring, something that Conroy believes has stood the test of time. “My idol has always been Tom Ford and then I also really love the King Charles suits and the Saville Row tailoring … it’s very structured, the shoulders are a little bit relaxed, with wide accents and lapels and longer jackets. I like the traditionalism and that’s one thing I try and keep in my own personal image and my clients’ image as well,” he said. “These suits have been around since the 17th century and I know people try to reinvent it, but it’s not something I like very much. What I fell in love with, and still love, is the traditional aspect of tailoring,” he added. And so, with the attention to detail, and the ambition to continue working in the field that he always had a passion for, Conroy took a leap of faith and started his own tailoring house - The Grafton Tailors - in July 2025. While he believes his passion for the job and the effort he puts into ensuring every client gets the highest standard of service has helped spread the word, becoming an entrepreneur might not have been possible if he was not in Dubai. Speak