Can you paint vinyl siding? The short answer is yes, thanks to advances in paint. In the past, it wasn’t possible to paint vinyl siding because of the way that vinyl siding expands and contracts throughout the year. Paint that mirrored the siding’s movement didn’t exist. But now, paints like latex urethane can handle the expansion and contraction. Prepare for a multi-day project when painting vinyl siding because the existing siding needs extensive cleaning and time to dry before painting.