(1) writing to communicate ideas, in which case simpler is almost always better. There's something hypnotic about simple writing (e.g. Paul Graham's essays) where information just flows frictionlessly into your head.
(2) writing as a form of self-expression, in which case flowery and artistic prose is preferred.
Here's a good David Foster Wallace quote in his interview with Bryan Garner:
> "there’s a real difference between writing where you’re communicating to somebody, the same way I’m trying to communicate with you, versus writing that’s almost a well-structured diary entry where the point is [singing] “This is me, this is me!” and it’s going out into the world.