I think the jeans look fine. They're slim/tapered enough for me to not confuse them with the vast majority of dad's jeans. Of course, I also like Ervell in his washed out Levi's. It's more early 90s to me than it is "dad jeans".
It's pretty hard to find skinny fits with high rises (I know, I've looked). Imperial's Shearer model comes to mind, but it's probably too tapered for what he wants. Next best thing for a straight fit might be Levi's Vintage Clothing 1947 501. The 36x38 will probably shrink down around 34x35 (but I believe the rise will only be about 12").
I thought the same thing about the scarf (it looks enormous). I like it, but I feel like maybe it would be less overpowering if it weren't pared with a completely slim outfit. Maybe it's just goth ninja groupthink creeping in, but I see it working best with more drape or some looser fitting items.
Are people really carrying food in these leather bags? I like this waxed canvas bag more than those leather ones,
But I would probably buy neither since a plain washable canvas bag seems like the most practical.
MelonadeJello is right, it's not a very laughable fit. If I saw him on the street with that outfit and those glasses I would immediately assume he is a mentally disabled person. The last thing I would want to do is laugh and point at someone like that.
Chunky boots can be worn with tapered pants. But your shoe and pant size will influence whether or not the shoes have a "clown shoe" appearance. I like the bottom pair. I was looking at those myself and would have probably ordered them if I hadn't just ordered some other boots.