I doesn't matter. It's Jamaica. It's always summertime there! and besides, where whatever you want to wear. who cares what others think. Besides, there are no rules in fashion anymore. Mix it up! Be hot! Look great! No worries, mon!
PLEASE I live in WI where it gets cold and that whole white after labor day thing is older than dirt! Hence the reason they make "winter white". Not to mention if you're in JA it's never "winter" so it's ok.