Help syncing with iTunes Outlook To Update iCloud

Hello Apple Community,
I have iPhone 4s and have just started to use iCloud. Can somone please tell me the best way I can use iTunes to sync to my Outlook Calendar & Contacts and then back this data to iCloud?
Forgive my lack of knowledge about this. I have always synced to iTunes for my Outlook Calendar & Contacts, but never sent this data to iCloud. Recently I lost all my Contacts & Calendar on the iPhone b/c I lost my PC hard drive (and to keep this story short) led to this new route of sending everything to iCloud.
I have searched for a few days but haven't found Tutorials on how to do this as yet.
So essentially what I am looking for is getting my Calendar and Contact data through iTunes to my iPhone and then send both the Calendar and my Contacts to iCloud.
If anyone can help me with this process I would be very appreciative hearing from you.
After the experience of losing everything and not being the sharpest person when it comes to understanding these things. I very much appreciate your help.

I've got similar problems with my old desk top running on Vista home premium, The problem started just recently (this year) and after iTunes had been updated. For two years I was syncing my Iphone 4S with Outlook 2007 with no problems. It just so happened that my wife's loptop was no longer reliable, so I bought her for Christmas a MacBook Air. After settng it up for her I realized the benefits and convenience having her Contacts, and Caleder on the icloud. She also has an iPhone 4S. I then decided to try and set up icloud with my desktop's oulook and my  iphone. At first it seemed that it was working although I felt something was not the same as before. It did not take long to realize that something undesirable was going on with my desktop. I could not figure out what. Looking into it I saw that iCloud (at least the latest version) could only be used with Windows 7 and 8. Having Windows Vista I proceded to remove iCloud from my desttop. In the process, to make a long story short, I had to remove iTunes and reinstall it without the iCloud. I found out removing iTunes is not as easy as it sounds. If you ever need to look it up elsewhre in this website, it requires a specific order of removing the components. By the way removing iTunes does not remove the Libtrary of songs (in my case a couple thousand). With the fresh installation my songs came back which made me happy. Reseting the fresh version of iTunes  to sync with my iPhone (not using the iCloud)  has not worked so far. Today is the second day working on it hope to get it going again.
By the way at one point I lost my contacts and calendar from my phone, however when I set the iPhone switches for iCloud all the contacts and Calendar data came back to my phone.

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