WPF

<ListBox>
                        <ItemsControl
                           ItemsSource="{Binding Path=AvailablePitchbookChartFamily}"
                           Width="100">
                            <ItemsControl.ItemTemplate>
                                <DataTemplate>
                                    <ListBoxItem
                                        Content="{Binding Path=DisplayName}"
                                        IsSelected="{Binding Path=IsSelected}"
                                    />
                                </DataTemplate>
                            </ItemsControl.ItemTemplate>
                        </ItemsControl>
                    </ListBox>

Private _objAvailablePitchbookChartFamily As ReadOnlyCollection(Of OptionViewModel(Of enumPitchbookChartFamily))

Public ReadOnly Property AvailablePitchbookChartFamily() As ReadOnlyCollection(Of OptionViewModel(Of enumPitchbookChartFamily))
        Get

            If _objAvailablePitchbookChartFamily Is Nothing Then
                CreateAvailablePitchbookChartFamily()
            End If

            Return _objAvailablePitchbookChartFamily
        End Get
    End Property

Private Sub CreateAvailablePitchbookChartFamily()

        '   We can't bind directly to the enum as we need to support multiple languages
        '   Map the enum to the resource file string here
        Dim obj As New List(Of OptionViewModel(Of enumPitchbookChartFamily))
        With obj
            .Add(New OptionViewModel(Of enumPitchbookChartFamily)(My.Resources.Strings.ChartFamily_Area, enumPitchbookChartFamily.Area))
            .Add(New OptionViewModel(Of enumPitchbookChartFamily)(My.Resources.Strings.ChartFamily_Bar, enumPitchbookChartFamily.Bar))
            .Add(New OptionViewModel(Of enumPitchbookChartFamily)(My.Resources.Strings.ChartFamily_Bubble, enumPitchbookChartFamily.Bubble))
            .Add(New OptionViewModel(Of enumPitchbookChartFamily)(My.Resources.Strings.ChartFamily_Column, enumPitchbookChartFamily.Column))
            .Add(New OptionViewModel(Of enumPitchbookChartFamily)(My.Resources.Strings.ChartFamily_Line, enumPitchbookChartFamily.Line))
            .Add(New OptionViewModel(Of enumPitchbookChartFamily)(My.Resources.Strings.ChartFamily_Pie, enumPitchbookChartFamily.Pie))
            .Add(New OptionViewModel(Of enumPitchbookChartFamily)(My.Resources.Strings.ChartFamily_Scatter, enumPitchbookChartFamily.Scatter))
            .Add(New OptionViewModel(Of enumPitchbookChartFamily)(My.Resources.Strings.ChartFamily_Stock, enumPitchbookChartFamily.Stock))
            .Add(New OptionViewModel(Of enumPitchbookChartFamily)(My.Resources.Strings.ChartFamily_Waterfall, enumPitchbookChartFamily.Waterfall))
        End With


        For Each objOption As OptionViewModel(Of enumPitchbookChartFamily) In obj

            '   Set the default value assigned in in Model for display in the view
            If Me.PitchbookChart.ChartFamily = objOption.GetValue Then
                objOption.IsSelected = True
            End If

            AddHandler objOption.PropertyChanged, AddressOf OnPitchbookChartFamilySelectionChanged
        Next

        obj.Sort()
        _objAvailablePitchbookChartFamily = New ReadOnlyCollection(Of OptionViewModel(Of enumPitchbookChartFamily))(obj)
    End Sub

Imports System.ComponentModel

Public Class OptionViewModel(Of TValue)
    Implements INotifyPropertyChanged
    Implements IComparable(Of OptionViewModel(Of TValue))

#Region " Declarations "

    Private Const UNSET_SORT_VALUE As Integer = Integer.MinValue
    Private _bolIsSelected As Boolean = False
    Private _intSortValue As Integer = Integer.MinValue
    Private _objValue As TValue
    Private _strDisplayName As String = String.Empty

#End Region

#Region " Properties "

    Public ReadOnly Property DisplayName() As String
        Get
            Return _strDisplayName
        End Get
    End Property

    Public Property IsSelected() As Boolean
        Get
            Return _bolIsSelected
        End Get
        Set(ByVal Value As Boolean)
            _bolIsSelected = Value
            OnPropertyChanged("IsSelected")
        End Set
    End Property

    Public ReadOnly Property SortValue() As Integer
        Get
            Return _intSortValue
        End Get
    End Property

#End Region

#Region " Constructors "

    Public Sub New(ByVal strDisplayName As String, ByVal objValue As TValue)
        _strDisplayName = strDisplayName
        _objValue = objValue
    End Sub

    Public Sub New(ByVal strDisplayName As String, ByVal objValue As TValue, ByVal intSortValue As Integer)
        _strDisplayName = strDisplayName
        _objValue = objValue
        _intSortValue = intSortValue
    End Sub

#End Region

#Region " Events "

    Public Event PropertyChanged As PropertyChangedEventHandler Implements System.ComponentModel.INotifyPropertyChanged.PropertyChanged

#End Region

#Region " Methods "

    Public Function CompareTo(ByVal other As OptionViewModel(Of TValue)) As Integer Implements System.IComparable(Of OptionViewModel(Of TValue)).CompareTo

        If other Is Nothing Then
            Return -1

        ElseIf Me.SortValue = UNSET_SORT_VALUE AndAlso other.SortValue = UNSET_SORT_VALUE Then
            Return Me.DisplayName.CompareTo(other.DisplayName)

        ElseIf Me.SortValue <> UNSET_SORT_VALUE AndAlso other.SortValue <> UNSET_SORT_VALUE Then
            Return Me.SortValue.CompareTo(other.SortValue)

        ElseIf Me.SortValue <> UNSET_SORT_VALUE AndAlso other.SortValue = UNSET_SORT_VALUE Then
            Return -1

        Else
            Return +1
        End If

    End Function

    Public Function GetValue() As TValue
        Return _objValue
    End Function

    Protected Sub OnPropertyChanged(ByVal strPropertyName As String)

        Dim handler As PropertyChangedEventHandler = Me.PropertyChangedEvent

        If handler IsNot Nothing Then
            handler.Invoke(Me, New PropertyChangedEventArgs(strPropertyName))
        End If

    End Sub

#End Region

End Class