I’m just going to come out and say it, both Microsoft and Apple are lame!
Apple first: Apple is lame on the issue for the following reasons. OSX Address book only exports VCF files or one big VCF file if you are doing all your contacts. OK, you could export every single contact individually, but that is going to take a couple hours. Secondly they are lame for not supporting Windows Live Mail the Windows 7 replacement for Outlook Express.
Now Microsoft is lame in that only Windows Live Mail can import a VCF file with 200 contacts in it. Albeit with much heartache and memory woes as your computer grinds to halt, fails to redraw the screen and has you click in some “Add” or “Import” or OK type of button that may or may not actually be displayed on the screen. When you are done your computer will require a reboot when the import is done. Outlook 2010 will import the first record in the VCF file. Windows Live Mail and Outlook 2010 cannot talk to each other.
So how do we get contacts into Outlook 2010?
You are going to need this on your Mac http://gwenhiver.net/address-book-exporter.html
This program will take allow you to export your Address Book to a TSV file. Get this file over to your PC. The next step is to import this TSV file in to Excel and save as CSV (Comma Separated Value) file. Outlook can import from this format. There is only one big caveat that I found, you will need to check the mapping for the import of e-mail addresses. I think this is due to a header problem in the CSV file.
There you go; now we have contacts. You had to buy Office 2010, but I bet you were going to do that anyway. (Actually I was going to give Open Office a go.)