Yo wannabe, why do you pose with your legs bowed way out like that? Anyway, jacket's a bit tight, and a wish the PS was a bit louder. I like the Chinos. Where are they from?
Wannabe, honestly I don't think that look is salvageable. That's clearly an orphaned suit jacket (whether you change the buttons or not) and you won't have much luck try to change the button profile. The shape is built into the canvas (or fused interlining) when the jacket is made. Trying to iron it may help but generally results in a deformed collar. My advice is find a new jacket with the qualities you're looking for and buy/save up for that one. As for pocket squares, just poof and stuff. Don't overthink it. Sometime just blow it off altogether. Re: pants. Try some proper dress pants. If you want an olive sport coat... tan or gray pants. In fact tan or gray pants will go with pretty much everything. Keep trying! Look at lots of pictures to find what you like and go check out the clothes in person.