I came across a requirement that needed the silverlight dropdown to show an image, only when the item has been selected after the dropdown has been closed. I have, however, showed an image with a label that shows a small description.
The code is given here:
<combobox x:name="cmbTest" itemssource="{..}" selectedvaluepath=".." width="52" selectedvalue="{Binding }">
<ComboBox.ItemTemplate>
<DataTemplate>
<StackPanel Orientation="Horizontal">
<Image Grid.Row="1" Margin="0,0,4,0" Source="{Binding image}" Width="25" Height="25" />
<TextBlock Text="{Binding YourProperty}" Margin="0,0,4,0" Visibility="{Binding Path=IsDropDownOpen,
ElementName=cmbTest, Converter={StaticResource BoolToVisibilityConverter}}" />
</StackPanel>
</DataTemplate>
</ComboBox.ItemTemplate>
</combobox>