How do I repaint furniture?

I have this dining set that I want to paint to match the rest of my house, which has a farmhouse feel to it. The top has a dark granite look, so there isn't much I can do about that. The rest is a glossy wood look. I was thinking about painting the legs and chairs white and distressing them and then redo the seats with a medium gray fabric.

First of all, do you think that would work and actually look good?

Second of all, how would I paint it? Do I need to strip anything off first? Is there a specific type if paint I need to use?

This is the best picture I have of it right now and I can't find it online. I would love to just buy a whole new set, but I can't afford it right now. I really don't like how dark this set is and just want to brighten it up.