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Have you ever tried painting fabric? The process is very different than painting furniture but I'm so pleased with the results!
When I found this $20 chair at the Habitat for Humanity Restore I walked past, admiring it, multiple times and even sitting down to test it out before I decided I couldn't leave without it.
Fabric - General Finishes Lamp Black milk paint (mixed with water & fabric softener to achieve a cake batter consistency)
Frame & Caning - Painted in General Finishes Antique White
Faux Wood Finish - achieved using General Finishes Glaze Effects in Van Dyke Brown
Sanding in-between coats on the fabric softened it quite a bit. I also waxed the entire piece after and it really seemed to help