OutSync: Sync your Facebook Friends with your Outlook Contacts
OutSync is a small little Windows application that is used to pull the pictures from your Facebook friends and apply that to the matching contacts in Outlook.
*Note: I have blurred the bulk of my contacts names, pictures and information for their privacy.
You can download OutSync from the link above, and installing is quick and painless. The first time you launch OutSync, it can take a minute or so to even show up. While you may think you misclicked or perhaps think the app didn't launch, give it a minute or two depending on the speed of your machine before you get too impatient.
Once OutSync is up and running you'll see a window like this prompting you to login with your Facebook credentials:

Once you have logged in OutSync will start pulling your friends list ( this can take a while depending on internet connection speed and number of friends ):

Once that's done you should see something like this:

This window lets you check off contacts that you want to sync and ones that you don't want to. The only difficulty I had was that contacts in Outlook and in Facebook have to match EXACTLY. So, if your friend on Facebook displays a middle initial or their entire middle name, you have to have it like that in Outlook for the match to be made. I'd like to see the ability to "link" a Facebook profile with an Outlook contact as well, without the name having to be a perfect match, but maybe that's a future enhancement.
Once you have selected the contacts that you want to sync you press the "Sync" button and the screen will change to something like:

Followed by:

Once that is done you can open up Outlook and see that the matched contacts do indeed have pictures now:

If you have an iPhone that syncs to Outlook or a Windows Mobile phone where you can use ActiveSync, you can easily then sync your Outlook contacts to your phone.