Shortening System.out - which is better?
With the second approach you hide that out refers to System.out, so if anytime later you want to redirect the output, you need to change only static final PrintStream out = System.out; since the rest of the code is only aware of the fact that it is writing to a PrintStream.

The first approach is just using the shortcut offered by static imports.

Which one to use depends on the purpose of the code. If it is a one time, throwaway code trying out something, then I'd go with the first, otherwise the second, if there are many print statements. Otherwise I would not care replacing System.out.

On the other hand I would consider using a logger instead of System.out and that could be redirected to System.out to a File and to many other targets.