Preliminaries
Grouping items in an ItemsControl in WPF (which DropDownButton derives from) is fairly simple, and is accomplished in two steps. First you need to set up the items source by tweaking an ICollectionView associated with the source collection. Then you need to populate the ItemsControl.GroupStyle collection with at least one GroupStyle item - otherwise the items are presented in a plain (non-grouped) manner.
Diagnosis
The main issue you're facing is getting the drop-down to present the items in a grouped manner. Unfortunately, unlike setting up the items source, it is not something that is easily accomplished in case of the DropDownButton control. The reason for that stems from the way the control (or, more precisely, its template) is designed - the drop-down is presented inside a ContextMenu attached to a Button which is part of the template (see MahApps.Metro source code). Now ContextMenu also derives from ItemsControl, and most of its properties are bound to corresponding properties of the templated DropDownButton. That is however not the case for its GroupStyle property, because it's a read-only non-dependency property, and cannot be bound or event styled. That means that even if you add items to DropDownButton.GroupStyle collection, the ContextMenu.GroupStyle collection remains empty, hence the items are presented in non-grouped manner.
Solution (workaround)
The most reliable, yet most cumbersome solution would be to re-template the control and add GroupStyle items directly to the ContextMenu.GroupStyle collection. But I can offer you a much more concise workaround.
First of all, let's deal with the first step - setting up the items source. The easiest way (in my opinion) is to use CollectionViewSource in XAML. In your case it would boil down to something along these lines:
<mah:DropDownButton>
<mah:DropDownButton.Resources>
<CollectionViewSource x:Key="LeaguesViewSource" Source="{Binding Leagues}">
<CollectionViewSource.GroupDescriptions>
<PropertyGroupDescription PropertyName="NationName" />
</CollectionViewSource.GroupDescriptions>
</CollectionViewSource>
</mah:DropDownButton.Resources>
<mah:DropDownButton.ItemsSource>
<Binding Source="{StaticResource LeaguesViewSource}" />
</mah:DropDownButton.ItemsSource>
</mah:DropDownButton>
Now for the main part - the idea is that we'll create a helper class that will contain one attached dependency property that will assign an owner DropDownButton control to the ContextMenu responsible for presenting its items. Upon changing the owner we'll observe its DropDownButton.GroupStyle collection and use ContextMenu.GroupStyleSelector to feed the ContextMenu with items coming from its owner's collection. Here's the code:
public static class DropDownButtonHelper
{
public static readonly DependencyProperty OwnerProperty =
DependencyProperty.RegisterAttached("Owner", typeof(DropDownButton), typeof(DropDownButtonHelper), new PropertyMetadata(OwnerChanged));
public static DropDownButton GetOwner(ContextMenu menu)
{
return (DropDownButton)menu.GetValue(OwnerProperty);
}
public static void SetOwner(ContextMenu menu, DropDownButton value)
{
menu.SetValue(OwnerProperty, value);
}
private static void OwnerChanged(DependencyObject d, DependencyPropertyChangedEventArgs e)
{
var menu = (ContextMenu)d;
if (e.OldValue != null)
//unsubscribe from the old owner
((DropDownButton)e.OldValue).GroupStyle.CollectionChanged -= menu.OwnerGroupStyleChanged;
if (e.NewValue != null)
{
var button = (DropDownButton)e.NewValue;
//subscribe to new owner
button.GroupStyle.CollectionChanged += menu.OwnerGroupStyleChanged;
menu.GroupStyleSelector = button.SelectGroupStyle;
}
else
menu.GroupStyleSelector = null;
}
private static void OwnerGroupStyleChanged(this ContextMenu menu, object sender, NotifyCollectionChangedEventArgs e)
{
//this method is invoked whenever owners GroupStyle collection is modified,
//so we need to update the GroupStyleSelector
menu.GroupStyleSelector = GetOwner(menu).SelectGroupStyle;
}
private static GroupStyle SelectGroupStyle(this DropDownButton button, CollectionViewGroup group, int level)
{
//we select a proper GroupStyle from the owner's GroupStyle collection
var index = Math.Min(level, button.GroupStyle.Count - 1);
return button.GroupStyle.Any() ? button.GroupStyle[index] : null;
}
}
In order to complete the second step we need to bind the Owner property for the ContextMenu (we'll use DropDownButton.MenuStyle to do that) and add some GroupStyle items to the DropDownButton:
<mah:DropDownButton>
<mah:DropDownButton.MenuStyle>
<Style TargetType="ContextMenu" BasedOn="{StaticResource {x:Type ContextMenu}}">
<Setter Property="local:DropDownButtonHelper.Owner" Value="{Binding RelativeSource={RelativeSource TemplatedParent}}" />
</Style>
</mah:DropDownButton.MenuStyle>
<mah:DropDownButton.GroupStyle>
<GroupStyle />
</mah:DropDownButton.GroupStyle>
</mah:DropDownButton>
This I think should be enough to achieve your goal.