98% of Women don't know what "well dressed" means. Just like 98% of guys don't. This includes you, and probably all of the girls you've ever tried to pick up. Girls like some pretty stupid shit on guys.  I recently read a thread on styleforum with a girl posting things she and her friends wish their boyfriends would wear. It was atrocious. Women basically have no clue. Some do... but not the ones guys are typically trying to attract when they dress to go to the club.
You could look at anyone's style and criticize it, but you'd have no idea what you're talking about. It'd sort of be like a weekend warrior criticizing Pollard and Pep's skiing ability. Some people know a lot more than you do about fit, colour, proportion, lines and quality in shoes and clothes, it's as simple as that. These people, however, do not wear hollister, and they don't wear the stuff Ajay wears either. I didn't read most of his posts in here, but I wouldn't be surprised if he DOES try to pick up fake, materialistic, and pretty hot bitches, and I'm sure his style is optimal for doing so. It's still pretty terrible though, in terms of, for example, fit, proportion, quality, and colour palette.
200 dollars is just what good jeans cost. Like I said, check out www.selfedge.com or www.denimbaronline.com, both have a great selection of well made raw jeans. I think the entry level of that kind of denim is the APC New Standard at about $145, going up to 300ish for various Japanese made brands. Paying 200 for much better made raw jeans is absolutely encouraged in my book. The problem is paying 200 (or in most cases now, 300+ for Rocks and Religions) which are poorly made, look ridiculous, and are only expensive because they're hyped. Thus the term "Hypebeast". Urbandictionary.com it.