Answers

Yes, you can paint vinyl shutters. First make sure they are throughly clean and dry. Then is they are glossy give them a light skuff up with a scotch bright pad or fine sandpaper. Finally I would recommend using a spray paint that is designed for plastic. You can buy this at most home improvment stores. Do a test spot first and make sure there are no reactions.   

Yes Vinyl can absolutely be painted! Be sure to clean it well before applying the paint.  Using a paint that has more sheen to it will bring a more protective finish.  Most customers of ours prefer using a semi-gloss or a gloss on the shutters.  

The shutters on my own home are painted, although not well. 

I think the consideration becomes is when the cost of painting them approaches about 70% the cost of new.  Shutters aren't terrible expensive and the ones that are on new construction homes have usually taken a beating for other reasons.

Don't get me wrong, I dislike throwing stuff away.  I would post up a picture of my garage if I wanted to be really embarrased, but if they are in good shape, paint them.  If not, replacements make sense. 

Windows on Washington

Yes. You can paint vinyl shutters. Clean and then use an acrylic latex paint made specifically to plastic materials.

Yes vinyl shutters can absolutely be painted, although maintenance will be required again with normal wear & tear and exposure to the elements. Have you considered replacing them with a low maintenance product? There are a lot of products that can offer the color you desire with the maintenance you also desire... little to none. Here are some examples of shutters that we replaced with low maintenance shutters. 

Yes, they absolutely can be painted.  Go to your local Home Depot, Sherwin Williams or Lowes for advice and color selection.  It is best to remove the shutters first.  This will probably make the job easier and you won't have to paint on a ladder if the shutters are located over one story high.  Next, check on the anchoring system.  If they are connected into say, a vinyl siding, you will probably wreck the plastic, ring shanked, fasteners.  You can get these at the above box stores as you will need new ones to re-attach the shutters when you are done painting them.  If the shutters are over brick, the removal process is a bit easier as you can simply remove the screws.  If this is the case, check the mortar anchors to make sure they are still well intact.  Most of all, have fun.  These projects can be fun and rewarding if you start with a good plan.

Yes vinyl can be painted! My recommendation is to make sure that all of the previous paint is removed, if any exists, and that the surface is smooth and dry. Also priming and sealing is the best way to make sure that your shutters stay in great shape for long periods of time. Hope this helps and good luck!

About 6 years back we installed replacement shutters on a 1930's era home. The origonal wood shutters were painted black but had serious rot issues after years of enduring the wet conditions of the Pacific Northwest. We decided to construct the new shuters with Azek PVC. Our Azek Rep. recommended that we use Sherwin Williams VinylSafe Paint. It resists UV heat gain and the shutters we installed still look great. Good Luck!