Managing multiple selections with MVVM

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Add an IsSelected property to your child ViewModel (OrderViewModel in your case):

public bool IsSelected { get; set; }

Bind the selected property on the container to this (for ListBox in this case):

<ListBox.ItemContainerStyle>
    <Style TargetType="{x:Type ListBoxItem}">
        <Setter Property="IsSelected" Value="{Binding Mode=TwoWay, Path=IsSelected}"/>
    </Style>
</ListBox.ItemContainerStyle>

IsSelected is updated to match the corresponding field on the container.

You can get the selected children in the view model by doing the following:

public IEnumerable<OrderViewModel> SelectedOrders
{
    get { return Orders.Where(o => o.IsSelected); }
}

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