Why are your pants so long and uncuffed in your "typical style?" The other suit was boring by SF standards but perfectly fine by the other 99.999999999999999% of the population who aren't fucking nuts.
Buy shirts that fit in the neck and have them tailored. You are probably too young for custom and they're not as cheap as some may say or you may want. This is going to be a problem for some time to come so might as well address it head on. Open collars are not a long-term option.
The shoes are fine for a guy in your position, whether you overpaid or not. But, unfortunately, asking a sensible question in good faith on this site does not immunize you from abusive responses from assholes. They just like to fuck with people.
P-Diddy, or whatever name he goes by. I admire his business savvy but as far as his music goes, forget it. I think he is better as an actor, actually. But, then I have to say I also think that, his immaculate grooming aside, he is not very good looking or in particularly good shape. I don't know who the hell buys his clothes, either.
Just finished Ian Frazier's "Travels in Siberia." "New Yorker" readers who know his stuff should not miss it--it is as entertaining as it is exhaustively researched. Now on a Martin Booth kick: His "A Very Private Gentleman" was the basis for the move "The American" with George Clooney. His 'The Industry of Souls" was great and I'm now on to "Hiroshima Joe." Check the reviews on Amazon if you need confirmation. Too bad he died several years ago; he was very prolific...