Winter in Seattle = Possible Crisis

So as we prepare to move- the one thing Kevin and I are actually nervous about is the weather change- especially since we will be moving right in time for winter. I've been looking up clothing styles and trying to get ideas for what we can buy for Kevin who owns three pairs of shoes: sandals, running shoes, and a pair of dress shoes I bought for him for our wedding. I have no idea what to do about him for the winter since he HATES shoes and doesn't exactly jump at the idea of buying winter coats, or jackets in general- he does not own an actual jacket.

Here is what I could maybe get him to wear while snowing:

However here is what he would probably want to wear:

And if I'm being honest, more like this guy in the background:

LORD HELP ME! Since this is what I found online when searching "mens winter fashion":

I mean I could probably get him to dress like that for the pure humor/ridiculousness of it- but hey- at least he'd have shoes on... Maybe I could find a happy medium with this...?

Or any of these...

I will keep you posted on our progress! Because lawd knows this will be a project. As for me.. I am looking forward to this... (Minus the awkward green coat lady)

and hope that we don't end up looking like these people...

Any winter tips for those ignorant of what "weather" really is!?