I personally HATE when guys wear skinnies. It's too feminine, and to be honest, it's not good for a guy's package. I like it when a man looks and dresses like a man. Stay out of MY wardrobe and leave the skinny jeans to me.
I like them loose, but not so loose you have to keep pulling them up. I don;t mind if they fall a little below the top of your boxers but any lower than that they are too big.
I like kind of baggy, bootcut jeans. Not so baggy that they're hanging past the rump, but just baggy enough to where the elastic band of the boxers are sticking out the top. And of course, not high- waters.