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? Haha, I honestly don't know about the legs. Maybe it's the way the picture was taken? The chinos are from Calvin Klein. 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. Argh...alright Parker. I think I'll try to iron the collar and see how that turns out. I still want to salvage the jacket; what buttons do you think would work? Or is it just that unsaveable ? . Thanks for your advise about the PS. And, excuse my ignorance, but what's the difference between proper dress pants and suit pants? Do the dress pants you refer to not have a belt loop, with this being the only difference? It's sort of hard to find things my size, so I'm relegated to the kids section of Calvin Klein. Unfortunately, they don't make a lot of 2-button jackets. Awesome shoe. Please share maker, model, and year!