Could not get this working using a DockPanel quite the way I wanted and reversing the flow direction of a StackPanel is troublesome. Using a grid is not an option as items inside of it may be hidden at runtime and thus I do not know the total number of columns at design time. The best and simplest solution I could come up with is:
<Grid>
<Grid.ColumnDefinitions>
<ColumnDefinition Width="*" />
<ColumnDefinition Width="Auto" />
</Grid.ColumnDefinitions>
<StackPanel Grid.Column="1" Orientation="Horizontal">
<!-- Right aligned controls go here -->
</StackPanel>
</Grid>
This will result in controls inside of the StackPanel being aligned to the right side of the available space regardless of the number of controls - both at design and runtime. Yay! :)