For this project, you're going to need acrylic paints and/or acrylic paint pens, a pair of shoes (you can get knock-off converse from wal mart for around 12 bucks), and some spray-on sealer. I use Wilson's Leather and Suede Protector.
First, spray every part of your shoes with your sealer. THIS IS VERY IMPORTANT. Without it, the paint will just seep into the holes in your shoes and the color will be very dull.
I always find it helpful to make a quick outline of what I'm about to do with a white paint pen before I start painting. But it's up to you. If you feel really comfortable with your painting ability, you can go ahead and wing it.
When you paint, be sure to do more than one coat, otherwise the paint will dry too darkly.
Once you're happy with your painting, spray the shoes again with your sealer to keep it from getting washed out by water.
Step 5: Aaaannndddd... you're done!
Let your shoes dry, lace them back up, and strut your stuff.