Charles played his first twenty20 match in January 2008, representing Saint Lucia in the Stanford Twenty20. Opening the batting with Keddy Lesporis, Charles managed scores of 2 and 21 from the only matches he played in the competition. Later that year he debuted for the Windward Islands in the West Indies Board Cup, the regional one-day tournament. His performances weren’t sufficient to secure a place in the team’s one-day side, and in 2009 Charles played neither List A nor twenty20 cricket. However, he made his first-class debut in January that year and played eight matches for the Windward Islands in the Regional Four Day Competition. In 16 visits to the crease he accumulated 292 runs, including a single half-century, putting him seventh in the team’s list of leading run-scorers in that year’s competition.
Charles did not represent the Windward Islands in the 2009/10 Regional Four Day Competition, but in 2010 he returned to the List A side for the West Indies Board Cup, and played his first twenty20 match for the team. In the first match of the Caribbean T20, Charles opened the batting with Devon Smith and exploited several reprieves (Charles was dropped three times and nearly run out) to score his first half-century in the format.
Having been selected in the West Indies squad for the 2012 Twenty20, Charles opened the bat with Chris Gayle in the third match (he batted after the fall of the first wicket in the West Indies opening match and in the second did not bat as the match was rained off). After building a century partnership with Gayle, Charles (who was described by ESPNCricinfo as having "little obvious pedigree as an opening batsman") went on to score 84 to help his team to victory against England. It was his highest score in first-class, List A, or even twenty20 cricket. The following month Charles was dropped from the West Indies squad to face Bangladesh in a five-match ODI series.