Outlook 2011 can import .pst files, but some users are reporting problems importing. I have tested some .pst files submitted by users that brought over no messages using Outlook import, but using Emailchemy I was able to bring over the data easily. I know Microsoft is looking into this issue, but in the mean time you might want to try the demo and see if will help with the transition to Outlook.
Emailchemy can convert .pst files to Entourage .rge files, which Outlook Mac can easily import. For best results, the conversion from .pst should be done on a Mac. Also, for very large .pst files (anything over a couple gigabytes), you should use the free utility, Emailchemy MemoryBoost, which helps by giving Emailchemy a ton of working memory. This helps Emailchemy deal with giant email messages and it helps Emailchemy complete the conversions faster.
Another shortcut Emailchemy can offer is that it can convert several.pst files at once into a single .rge file, so that you only have to import one file into Outlook.
Convert .PST file using Emalichemy
Click on the circled tool button to start.
Select file type .pst
Browse to the location of your file and click on the Convert button. Your file will be saved as an .mbox file or .rge. The Entourage archive (.rge) is an easier import if you have a lot of folders.
Note: When you click the “Convert” button, the save dialog that pops up will have a drop down box where you select the format to which you want to save. Just like if you were saving a file in Photoshop, you need to select the format of the saved files. Standard mbox is the default, but for Entourage RGE you just need to select the “Entourage Archive (RGE file)” option from the drop down list.
The mbox files that Emailchemy creates when you select “Standard MBOX” are readable by Apple Mail, Entourage, Thunderbird and almost anything else, but the .mbox folders that Emailchemy creates when you select “Apple Mail” format as the output are only readable by Apple Mail.
Import the .mbox file into Outlook
Under File in the Menu bar, select Import. Select Outlook Data file (.pst or .olm)
You’ll find the imported file in the folder list. Toggle open to view messages. Copy messages or drag folders to their desired location then delete the remaining empty folders.