At age 10, he was selected to perform the role of Tiny Tim with the Royal New Zealand Ballet's production of A Christmas Carol, which included touring New Zealand with the company.
As a Paraparaumu College student in mid-2005, he travelled into Wellington three times a week to attend vocational level ballet classes at Paula Hunt Dance and, in 2006, won the Royal Academy of Dance (RAD) 14+ Scholarship.
The win encouraged James to leave college and pursue his passion for dance, entering into full-time dance training at the New Zealand School of Dance with a classical major in 2007.
That year, having caught the eye of visiting tutor Anna Marie Holmes, he was offered a scholarship to attend the Jacob's Pillow Summer School, Massachusetts, in June 2008.
According to his mother Bronwyn Wynn, he made the most of his travel by applying for a scholarship to attend the San Francisco Ballet School Summer School (SFBS), which he attended afterwards.
"James received widespread financial assistance from Kapiti individuals, community groups and dance organisations for that trip, which may not have been possible otherwise, and he remains deeply grateful to all his supporters," Ms Wynn said.
At the completion of the SFBS, the budding young dancer was offered a place in the school's Trainee Programme, where he spent the next two years in San Francisco under the tutelage of director Jean-Yves Esquerre.
As his career quickly developed, Wynn was offered a contract in San Francisco Ballet's corps de ballet but, unable to secure a US work visa, he took up a corps position with the Royal Winnipeg Ballet in Alberta, Canada.
At the end of the first season, he was promoted to Second Soloist and then to First Soloist not long after, having impressed with his performance as leading role in choreographer Mark Godden's new self-influenced work Svengali.
A successful audition for Bejart Ballet in Lausanne, Switzerland, followed, where he spent a year performing works choreographed by Maurice Bejart and touring with the company to the likes of France, Italy, Russia, Japan and South America.
"He was drawn back to Canada by the desire to perform classical ballets again, live in an English-speaking country and cement a relationship," his mother said.
After eight weeks recovering from a foot injury, his repertoire expanded to include lead roles in Manon, Romeo and Juliet, Carousel (A Dance), The Sleeping Beauty, The Winter's Tale, Le Petit Prince and Giselle.
Toronto publication The Globe and Mail recently described Wynn as "an elegant classicist with striking poise and emotional depth".
"James can do melancholy without getting maudlin," it said. "His charm always comes with a bolt of seriousness, a flash of verve."
According to the Canadian-based publication, traditional ballet companies usually relied on a bottom-heavy hierarchical pyramid, with many dancers spending 10 to 15 years of their careers performing the background choreography of the corps de ballet. Not Wynn, however.
"Imagine the most dashing and magnanimous princes of 19th century literature and you'll conjure an idea of his magnetic presence as a performer."
