A painted checkerboard pattern on a floor evokes a folksy, rustic, farmhouse simplicity--which is ironic, because it's actually a pretty complicated project. You have to stencil in the pattern using painter's tape, which sounds easy enough, but since the corners of the painted squares meet, you have to skip a row each time (instead of painting the whole grid at once) to accommodate the thickness of the tape--all the while making sure the end result will fit together. Use good floor paint, and choose your colors carefully, as you don't want to have to redo this.
Whether you're painting your floor with one color, two colors in a checkerboard pattern, or your own rendition of the Mona Lisa, getting the paint to stay on the floor is always a challenge. Whatever material is covering the floor to start with has to be flat, clean, and free of gloss. Use a belt sander with 80-grit sandpaper to go over the whole floor, working the surface until you can look at it from various angles and not see sharply reflected light. Clean up the dust, then use a floor roller to apply a thin layer of flat sealing primer, which will give you an even color field to start with and assist in getting the paint to stick.
Checkerboard patterns look like intermingled squares, but they're actually a full-room base color with squares of a second color laid on top. Paint the whole floor in the lighter of your two colors, using a floor roller. When it dries, lay out the squares for the darker color. Do this by dividing the room into four even squares with a chalk snapline, measuring from mid-wall to mid-wall in both directions. Measure from the middle intersection of the squares out to the wall to figure out what size of smaller squares will fit evenly to the walls. Once you've determined the size of the squares, mark the whole grid out on the floor with your chalk snapline.
Start painting on the squares in the darker color from one side of the room. Lay down painter's tape all along the outside edge of the first row, from wall to wall, with shorter pieces of tape in between to mark off each square. Paint the darker color within the taped squares. Skip a row, then tape and paint again. Continue until you've done every other row in the room. Pull up all the tape and let the paint dry, then follow the same process for the rows you skipped before. Once your whole pattern is done, top it with two or three coats of floor-grade polyurethane gloss.
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