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    <p>Use ItemTemplateSelector:</p> <pre><code>public class MenuItemTemplateSelector : DataTemplateSelector { public DataTemplate SeparatorTemplate { get; set; } public override DataTemplate SelectTemplate(object item, DependencyObject container) { var menuItem = container.GetVisualParent&lt;MenuItem&gt;(); if (menuItem == null) { throw new Exception("Unknown MenuItem type"); } if (menuItem.DataContext == null) { return SeparatorTemplate; } return menuItem.ItemTemplate; } } </code></pre> <p>Xaml:</p> <pre><code>&lt;ContextMenu DataContext="{Binding PlacementTarget.DataContext, RelativeSource={RelativeSource Self}}" ItemsSource="{Binding Path=ViewContentMenuItems}" &gt; &lt;ContextMenu.ItemTemplateSelector&gt; &lt;templateSelectors:MenuItemTemplateSelector&gt; &lt;templateSelectors:MenuItemTemplateSelector.SeparatorTemplate&gt; &lt;DataTemplate&gt; &lt;Separator /&gt; &lt;/DataTemplate&gt; &lt;/templateSelectors:MenuItemTemplateSelector.SeparatorTemplate&gt; &lt;/templateSelectors:MenuItemTemplateSelector&gt; &lt;/ContextMenu.ItemTemplateSelector&gt; &lt;/ContextMenu&gt; </code></pre> <p>In model:</p> <pre><code>public ObservableCollection&lt;MenuItem&gt; ViewContentMenuItems { get { var temp = new ObservableCollection&lt;MenuItem&gt;(); temp.Add(null); temp.Add(CreateFolderMenuItem); return temp; } } private MenuItem CreateFolderMenuItem { get { var createFolderMenuItem = new MenuItem() { Header = "New Folder", Icon = new Image { Source = new BitmapImage(new Uri("/icons/folderWinCreate.png", UriKind.Relative)), Height = 16, Width = 16 } }; Message.SetAttach(createFolderMenuItem, "CreateDocumentsFolder");//Caliburn example return createFolderMenuItem; } } </code></pre>
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