If I paint my walls a shade of gray. Can I leave my base boards oak?
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Of course, but pick your gray that doesn’t make the oak look too orange or yellow. Get “tester” jars.
There are so many gorgeous grays. It will look fabulous
I think a soft gray wall framed by your oak baseboards will lend a creativity to the room. Just remember to tape using a good painters tape.
You don't have to paint them white, especially if all the other trim in your house is oak. It will look great with oak trim!
Samples painted toward the base of the wall would be ideal..... grays that are too "blue" could make the oak look orange....... there is also the option to use a grey "wash" on the oak to tone down the orange aspect.
It’s a matter of taste. Just remember that once you paint them to match the grey you can’t go back to wood. You might just want to think of it as a ‘neutral.” Probably you’ll want to replace the grey in the future so if you paint them grey, you’ll have to paint them again.
Here are many examples. Often gray is suggested as a colour to complement orangey oak cabinets.
https://www.google.ca/search?q=gray+walls+with+oak+trim&source=lnms&tbm=isch&sa=X&ved=0ahUKEwid5oDjxurbAhUOo4MKHag2DqEQ_AUICigB&biw=1396&bih=690
https://www.kylieminteriors.ca/the-best-paint-colours-to-go-with-oak-wood/