I have painted and striped, cars and vans my whole life.
Painting on stripes requires the right type of paint, and good technique.
Save yourself a lot of trouble, and don't paint them, use the stripe tape.
Remove the backing about an inch, (if there is one), and place one end of the stripe, on the end of the item your striping. Unroll enough stripe to go the length of your project. Holding the tape taught, and away from the surface, remove the rest of the backing. Pull the tape straight and gently lay it against the surface. If the tape is where you want it, gently finger it down, then press hard to set the adhesive. If it is not where you want it, you can lift and reset it. Cut the ends while holding them above the surface, with a brand new razor blade. DO NOT CUT THE PAINT. Pinstripes usually have a clear protector on top called a liner. If there is a liner, peel it back with your finger, or use a piece of masking tape to lift it, and remove it completely.