We have a Person who can have several Skills (Strength, Intelligence and Luck). In our WPF-Application, we want to bind these Skills to Checkboxes. When a Person has these Skills in his list, then the Checkboxes should be checked:

The Person Class and Enum:

public class Person
{
    public string Name { get; set; }    

    public List<SkillsEnum> Skills { get; set; } // <-- The skills of the user
}

public enum SkillsEnum // <-- All available skills
{ 
    Strength,
    Intelligence,
    Luck
}

Our View Model:

public class InitAppViewModel : ViewModelBase
{    
    public Person CurrentPerson { get; set; }

    public IEnumerable<string> AvailableSkills
    {
        get { return Enum.GetNames(typeof(SkillsEnum)).ToList(); }
    }

    public InitAppViewModel()
    {
        CurrentPerson = new Person() { Name = "Foo", Skills = new List<SkillsEnum> { SkillsEnum.Luck, SkillsEnum.Intelligence } };
    }
}

The respective XAML-Markup:

<ItemsControl x:Name="CurrentPerson_Skills" ItemsSource="{Binding AvailableSkills}">
    <ItemsControl.ItemTemplate>
        <DataTemplate>
            <CheckBox Content="{Binding}" IsChecked="{Binding RelativeSource={RelativeSource AncestorType=ItemsControl}, Path=DataContext.CurrentPerson.Skills, Converter={StaticResource SkillToBoolConverter}}" />
        </DataTemplate>
    </ItemsControl.ItemTemplate>
</ItemsControl>

The Converter:

public class SkillToBoolConverter : IValueConverter
{
    public object Convert(object value, Type targetType, object parameter, CultureInfo culture)
    {
        // conversion code here which returns a boolean
    }

    public object ConvertBack(object value, Type targetType, object parameter, CultureInfo culture)
    {
        throw new NotSupportedException();
    }
}

How can we pass the Enum-Value of the Checkbox-Elements and the Skills of the Person into the SkillToBoolConverter so we can validate the skills and return true/false so that the checkboxes are checked/unchecked?