Can you dye leather
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Yes, and you can paint it too.
You can but it doesn't last that long and it will peel off like skin
Yes, check with your local arts and crafts store or Tandy leather for supplies and instructions
For sure, there are special leather dyes for such a project http://www.ebay.com/gds/How-to-Dye-Leather-For-All-Smooth-Leathers-/10000000000877002/g.html
My sister and I had a couple of old leather purses that were good quality but looking a little worse for wear. We both used strong rit dye - just soaked the purse in it and then hung it up to dry. That was years ago and the color has not faded. This would only work for a small item, tho.
Don't use a paint on real leather! I used to work with real leather (not pleather); make sure to clean first, make sure it is dry, only then should you stain it. It can look brand-new.