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There are two types of shutters; wooden shutters and vinyl shutters. Wooden shutters can and should be painted approximately every 5 to 7 years. Some vinyl shutters can be painted while some cannot. The only reason to paint a vinyl shutter is if you want to change the color. If they look worn or really dirty, vinyl shutters can be power washed or scrubbed with hot soapy water along with a good rinse.
If you think you want to paint your shutters and you know they are vinyl, take one down and look carefully at the back of the shutter. If you see something stamped into the back of the shutter that says "Unpaintable" or "Do Not Paint", then don't. You're done. You'll regret trying. If they are unpaintable and you can live with the color, and they are oxidized, you can bring them back to life with something like Armor All. If there is nothing stamped on the shutter prohibiting painting, then Krylon has some very good paint for vinyl. Ask your dealer which products are best for your shutter. Don't be afraid to bring a shutter in, either. They will help you determine the best paint products to use.
If your shutters are wooden, and this is a handyman project you can wrap yourself around, then take your shutters down and start out with a good cleaning. If they have paint chipping, you'll need to get a scraper and go to work. Be careful not to gouge the wood itself. Finish off the surface prep with some 80 grit sandpaper. You don't need a super smooth surface since it's an outdoor application, but make sure all the chipping is removed and you have a fairly smooth surface. You should prime your shutters since it is a pretty sizable job, and you'll want your final paint to last as long as possible.
Your paint can be oil based or water based, but make sure it is exterior grade. You can thin oil based paint a little with paint thinner but you'll probably need to do at least 2 coats. Remember, 2 coats are way better than 1, and 3 coats will give it an awesome finish. If you don't have a sprayer you can brush it, but I highly recommend thinning down your paint and applying multiple coats. There are also products you can buy that remove brush marks for both oil based and water based paints. For around ten bucks you can buy an additive that will give you final coat a very smooth finish.
Some tips when painting your exterior shutters: Let your paint dry all the way between coats. Most paints will have guidelines for minimum times between coats on the label. You can lightly sand in between coats to get the best adhesion as well. Talk to someone with experience about color coordinating with the rest of your house so your shutters will blend and compliment your house colors. Remove all your shutters at one time and follow an assembly-line pattern for the entire project. It will save time over trying to paint one or two at a time.
As you can see, giving your home exterior a facelift with a fresh coat of paint on your shutters is not at all hard to do and depending on how many you have, it's not ridiculous to plan it as one of your weekend handyman projects. Or maybe two. Finally, remember that shutters give a house a very classic look and ad to the appeal of your home tremendously. Even terribly worn shutters can be refurbished with just a little bit of work, and it's definitely worth the effort it takes to get them back in shape.
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