Neither 32 or 64 bit version will install
In cases where neither the 32 and 64 bit version of the ClearContext installer will install, reporting that the 32/64 bitness of Outlook does not match ClearContext, there is likely conflicting information in the Windows registry on whether Outlook is 32 or 64 bit. This can be caused by having 32 and 64 bit versions of Outlook installed at different times.
You can verify whether your Outlook is 32 or 64 bits by going to the Outlook File->Office Account->About Outlook screen (may vary by version). By the full version number will be listed 32 or 64 bit description.
If the installer is warning you about a 32/64 bit mismatch mistakenly, then you can override the warning and proceed with the installation.