his is a common question asked by Windows switchers, and the solution isn't as easy as it should be. There are several methods each with their own pros and cons. Choose the one that best meets your needs.
An easy (and free) way to transfer email from Outlook (Windows) to Mail (Mac) is to use an IMAP account (e.g. Gmail) as an intermediary between the two. It's simple and reliable but can be a bit slow for large amounts of email. Expect over an hour per Gigabyte.
- Enable IMAP on your email account. 
- In Windows, open Outlook and add your IMAP account. 
- Copy the folders (don't drag and drop them) from your PST file into your IMAP account. Drag and drop will move (not copy) your folders and you may lose mail if the communication is interrupted during the move.
- On the Mac, open Mail and add your IMAP account. 
- If you want your mail stored on your Mac, you can copy it from your IMAP account to mailboxes created by selecting "On My Mac" as the location in the new mailbox dialog inside the Mail application.
For another fairly easy migration, you can use Eight Hoof's 8Convert program ($14 shareware), which runs on your PC and directly exports files for use with Apple Mail. Theuserguide gives instructions on everything from install to file copying to importing into Apple Mail.
The program exports Outlook data to industry-standard mbox, vCard, and iCal formats that can be imported into Apple's Mail, Contacts, and Calendar programs, as well as compatible programs such as Entourage.
This alternative is free, mostly automated (no renaming of folders) but it requires a separate application, i.e. Thunderbird.
- Install Thunderbird. On first launch, tell it to import from Outlook (not Outlook Express).
- It will import account settings, contacts and email.
- Copy your Thunderbird profile (XP:
C:\Documents and Settings\, Vista/7:
\Application Data\Thunderbird\Profiles\ .default
C:\Users\) to your Mac. Several methods can be used to perform the copy operation:
- If both computers are on the same network, file sharing can be used.
- If the computers are NOT on the same network, the fastest approach is to zip-compress the profile folder in Windows, put it on an external storage device, bring the device to your Mac, connect it, and decompress the zip file.
- Start the Mail application and go to File > Import.
- Select Thunderbird and point it to the profile folder you copied to your Mac. The imported mail will be under "On My Mac".
- To be safe, you can go to "Mailbox > Rebuild" inside Mail to make sure there's no corruption resulting from the import.
This option can be done without the need for installing additional software on your PC but it will require Entourage (or Outlook) on your Mac which you may not have.
- Open Outlook Express on your PC.
- Highlight all mail in a folder e.g. "important mail", and drag them into a any folder on your hard drive (ideally - outlook mail/important). Having Outlook run in window mode (not fullscreen) and dragging the mail to a folder on your desktop seems to be the easiest way, because you don't have to switch windows.
- Make as many folders and fill them this way as you have/need, then copy them to your Mac.
- Start Entourage (or Outlook) on your Mac (if you have either of them).
- Drag them into a folder the same way as you exported them on your pc.
- Now you should have the mail in Entourage.
- Mail can now import mailboxes from Entourage.
Once you've imported all your email into the Mail application, you can delete all the other email from your desktop/Outlook/Entourage to save space.