First thing to try would be to rebuild the icon cache on your machine, it's an option from TweakUI - download it from the Microsoft site and give it a whirl.
One question too - is it the original icon? Or have you used an applicaton such as iconStudio, MircoAngelo or similar to change it? If so then check the folder where your icons were stored hasn't moved, as it can also cause what you described.
Heh, ok - well option two is to cheat and use one of the aforementioned apps to replace the icon yourself. Just point it at the outlook.exe and it will use the icon. I'll google to see if i can find some common causes and exactly where it's referenced in the registry.
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