In your second sample, try to use the WrapPanel inside a ItemsPanelTemplate for the ItemsControl, otherwise the ItemsControl uses a StackPanel by default and your WrapPanel doesn't do anything as there is nothing to wrap.
This is happening because the ItemsControl, by default uses a StackPanel in vertical orientation to layout it child objects. So the wrap panel is actually only laying out one child which is the ItemsControl. What you wan't to do is set the ItemsControl's ItemsPanel property so that is uses a WrapPanel for layout.
Your code would look like this.
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