Become a MacRumors Supporter for $50/year with no ads, ability to filter front page stories, and private forums.
What i've done is the following:

Configure gmail to be used as an imap service on your mail.app (on your mac)

copy all the mail from the mail.app to that gmail account.

Next; go to the windows machine, again configure the gmail account as an imap service and sync the account. that will give you the mac mail on the PC.

next you copy the gmail mail to your outlook mailbox(es)...

enjoy
 
Register on MacRumors! This sidebar will go away, and you'll see fewer ads.