 <p>in your solution consider changing</p> <pre><code>&lt;Trigger Property="MenuItem.Header" Value="enums:AnEnum.ItemA" &gt; </code></pre> <p>to </p> <pre><code>&lt;Trigger Property="MenuItem.Header" Value="{x:Static enums:AnEnum.ItemA}" &gt; </code></pre> <p>in your example you check that header is equal to <strong>sting "enums:AnEnum.ItemA"</strong> not to enum AnEnum member ItemA.</p>