Can't figure out a color to paint dining set
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A nice shade of gray will look nice.
Are the chairs upholsteted? Recovering them is really easy to do with a staple gun and not a lot of fabric is required. I'd go to a fabric store or the Walmart fabric section and pick up a fabric that you fall in love with that will help you decide a color. Use chalk paint which covers everything with no sanding, dry between coats. With a table I would put on two coats of wax on the top
Any color you like! Something to at matches the room it is in, something to contrast to the room it is in. Its all up to you and your preferences. Black or white is always a safe bet. Two-toned is usually good for that retro 50s furniture, like darker wood top, maybe a mahogany, and then lighter, maybe pickled white or cream legs and sides... The possibilities are endless.
I'm not big on painting dining room sets; but you could just redo the original stain that's already on there. If you really want to paint it white works very well.
I love steel blue :)
If you have fabric on the chairs; yes I would reupholster for a fresher look; putting stain on any of it I think is a great idea; rich looking.