To move entries to a different spot in the outline, first select the entry, and then use click the Move Up or Move Down button on the Outlining toolbar until the entry reaches the spot you want.
If the entry you're moving contains sub-entries and you want to ensure that the sub-entries move with it, be sure to first click the plus sign next to the entry before using the toolbar buttons. This selects the entry and all sub-entries so that they move as a unit. Doing this works whether the top-level entry is expanded or collapsed.
Tip You can also drag entries to their new position. Once again, if you want to move sub-entries along with an entry, be sure to first click the plus sign.