+1 for using Gmail/Google calendar, contacts (and Gmail to "fetch" your pop3 emails). You can easily import your Outlook data to your Google account. Then, add that account (Gmail) to your iPhone's accounts. That's all you will need. From that point on, everything will sync instantly, whether you make changes on your iPhone or PC/Mac. It's outstanding in its effectiveness and simplicity. Best of all, there's no chance of losing data if your iPhone or computer crashes. It's stored in Google's cloud. Another advantage, your computer(-s) and any cell phone having the account, will all be totally current at all times - automatically.
I used Outlook with Gmail for a while, until I realized I was doing double the effort. Outlook isn't needed.