Picture #1 His faded black jeans go together with his faded black shirt. If he would of worn a brand new black shirt he would of looked too manufactured. It is important when buying these different washed jeans that the shirt is appropriate, because if the outfit mismatches and matches at the same time, it will look like you are trying way too hard. Let me say that again, if the outfit mismatches and matches at the same time it will look like you are trying way to hard. If the shirt was a brand new black shirt it would of matched, but you need a faded black shirt to make it REALLY match. His brown shoes is a clash on purpose, which is what makes it work. He was trying to throw you off which is exactly why it works. Picture #2 This outfit is one belt away from being “too” put together. It works because the shirt matches the shoes, the first two things any ones looks at. Secondly he has a wash in jeans that makes the white stick out, going along with his blue and white theme. He rescued himself by wearing accessories away from white and blue. His brown cuffs and his green belt, stray away from too much white but all in all this why it works. Had he worn a white belt with a white watch then he would have gone too over board. If your jeans are going to be worn to aid in your attempt to match; be careful it is not too much. This guy’s accessories did a great job a taking way from that.