I'm trying to mimic this look from the Outlook's Image contextual tab.
Hello,
If you are referring to the 'Picture Shape' and the tools below it - you could set their caption and image from 'SharedProps'. The 'Caption' property is right under it and the image I suppose is under the 'AppearancesSmall'. Otherwise, the tool with the four pictures inside it is a 'PopupGalleryTool', you could read about it at the following link: http://help.infragistics.com/NetAdvantage/WinForms/2011.2/CLR2.0/?page=WinToolbarsManager_PopupGalleryTool.html.
Please feel free to let me know if I misunderstood you or if you have any other questions.