7. Leon Kennedy's Jacket from Resident Evil 6
Aside from how negatively some fans view Resident Evil 6, there's not too much hate out there for Leon Kennedy. His jacket and hair are certainly his most memorable traits, so they would be an awesome addition to Skyrim's world. Leather is a common resource in Skyrim, so this one wouldn't be too hard to craft. Should probably be a light armour, though.
6. Idiana Jones' Outfit
One of the main draws of Skyrim is exploring and raiding ancient crypts and tombs, and no one does it better than Indy himself. Sorry, Nate. The iconic fedora and whip wouldn't look too out of place in the streets of Tamriel either, there are certainly some stranger mods out there. The man bag could be used in a similar fashion to Nathan Drake's weapon holsters, a device used to increase inventory capacity. The rest would hopefully fit into the light armour category, but I doubt it would provide any real protection in real life. Luckily, this isn't real life.