In theory it doesn’t matter where you format it, but I’d always prefer OS X as 
it’s more thorough.  Just make sure the format is FAT32 or ExFAT; never NTFS or 
OS X.  In Disk Utility on OS X this is pretty painless; choose the disk from 
the table, and then press Erase in the toolbar.  Set the name and format.

Now copy your iTunes folder onto the stick, and then copy from the stick onto 
the target Mac inside your Music folder (deleting any existing folder that 
might be there).  You want the entire folder called iTunes, including all of 
its contents.  Make sure neither copy of iTunes is running while you are doing 
this.  Hopefully, when you next relaunch iTunes, it should identify as being 
the same library as was running on Windows for syncing, although you probably 
will need, as Jonathan said, to visit iTunes Preferences and make sure things 
are as you like them.  It might be a good idea, before you start this process, 
to transfer purchases and back up your device on your Windows machine; that way 
you can always come back to it if things should somehow go pear-shaped.

Good luck.

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