Organizing and accessing contact information in Outlook.com
Yes, Winphone 8 will also display images you've added through the People app, which is how I do it.
So that's good, yet those still don't sync back to Outlook 2013 or Outlook.com, so still a bifurcated experience to some degree. The People App, Outlook.com, Windows Phone 8 and Outlook 2013 should all be getting their images from the same source if the user overrides the default social network photos and adds their own.
Interestingly enough, Mail and Contacts on iOS also syncs my contact photos from Win 8.1. Yet, Outlook 2013 still doesn't.