fabric paint should flex more than regular paint, but it works better when you put it on porous fibers. I believe wind breakers are made of synthetic and coated materials that are designed to not absorb water (& paint). So it would be like a scab or film lying on top of the fibers, waiting to be rubbed off.
You could try getting a polyester windbreaker in white and then using ipoly to dye the pink area and the black area (two separate dyelots). That stuff works surprisingly well.