I'm always pushing this brand, but Naked and Famous hasn't let me down yet.
If $150 isn't working for you, they make a lower end brand called Unbranded, which is like $60ish on average.
Truth be told, in the pics you posted with brehs from your area, the third pic down not breh on the right got a fit I'd rock for the jeans.
It wasn't all bad breh.
But yeah, I'd turn down some of the branding, and just plain upgrade the general aesthetic.
Hit up Zara and Asos for shirts that'll be toughie but inexpensive.
J's are cool but not the necessary imo.