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Giving new life to old vinyl furniture using spray paint! While this pattern is a bit bold for me, I think you could do so many fun and subtle things to save an otherwise dated, ugly chair from being cast aside. (And all it takes is a little time, spray paint and painters tape!)
Furniture Makeover: The best spray paint for wood chairs. Spray Painting tips - In My Own Style
My rule of thumb is this. Prime these surfaces: 1) anything meant to go outdoors that will be exposed to moisture because you risk rust (but see below), 2) glossy surfaces, or 3) wood. Forget everything else.