I am sure there is a way from Apple Cloud services or even via iTunes. but the only way I have done it was via emailing the photos or MMS attached in both or either. I then just save the photos to my pictures folder. Then in my contacts I assign the photos that way. A pain I know.
I have never done it from the computer . You may go to http://www.apple.com and under forums you can search for that answer.
Having a face to match the contact if always a great way to spruce up the layout of your phone. I did the same and went from bland to grand so let's do that for you too.
Now, there are definitely a few different ways you can accomplish this. A few of the more popular routes, as suggested by a fellow poster, are to either utilize iTunes or even e-mail each picture to your phone (the process of which is dependant on your respective computer). If going the iTunes route though, you'll want to download it to your computer to start at http://bit.ly/9aRuhJ . Once on your computer, you can transfer your computer's saved media files to the platform and then to your device when hooked up while running a sync. I hope this helps out and if you have any further questions or concerns, I look forward to hearing back.
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