A device for applying a painted pinstripe to a surface includes a paint applicator having an adaptor for attaching a paint striping wheel head to a low profile paint container. A traveler adjustably coupled to the applicator is moveable along a magnetized flexible guide track in order to control direction of the paint applicator as an annular paint carrying surface of the striping wheel is rolled against the surface being pinstriped. The paint applicator is adjustably positionable on a connecting arm extending from the traveler for controlling and adjusting the distance of the striping wheel relative to the guide track. The paint applicator is also pivotally adjustable relative to the connecting arm and the guide track to accommodate for variations in surface configuration and contour so that the annular surface of the striping wheel is maintained in flat contact with the work surface to produce a uniform painted pinstripe.