Do These Go?

This goes in quick questions/answers.

First of all: those shoes are pretty poor knockoffs on Vans. Yeah, Voi is a decent brand blah blah blah, but get a pair of Vans instead. Blue plimsolls are pretty versatile and go good with all sorts of jeans (except for bootcuts), so yes. Get a pair plimsolls.  

Second: those are not good looking jeans. They are an abomination meant as workwear. You should never, ever, wear those out of a work-related situation where they're actually useful.

You want to get less "chavvy" and you would buy those jeans?

Re-examination needed. 

That polo is horrible, I suppose they all "go" colours wise, but they're all kind of awful.

If you're looking for nice, cheapish jeans, go for some uniqlo ones. Uniqlo is good for shirts, and if you really have to, polos too. 

I always find vans to look kind of disproportionate, but if you really want something that looks like vans go for real vans, but a better shoe would be a pair of white cons, you can never really go wrong with them.