Add a tooltip to the OutlookBarItems when the OutlookBar is minimized Approach to implement: Descriptions of the minimized RadOutlookBarItems can be achieved in WPF via: <Style TargetType="telerik:RadOutlookBarItem" BasedOn="{StaticResource RadOutlookBarItemStyle}"> <Style.Triggers> <DataTrigger Binding="{Binding RelativeSource={RelativeSource AncestorType={x:Type telerik:RadOutlookBar}}, Path=IsMinimized}" Value="True"> <Setter Property="ToolTipService.ToolTip" Value="{Binding RelativeSource={RelativeSource Self}, Path=Header}" /> </DataTrigger> </Style.Triggers> </Style> or by adding this trigger to the RadOutlookBarItem's ControlTemplate.Triggers