Sorry, but I disagree with them going with boot cuts. Prefer a slim or straight. The shoe has too-rounded a toe to look good with boot-cuts IMO. But, then, I am not a fan of boot-cuts, so I guess I am biased.
Amen to the "oversized" comment. I had a Filson Halsey that was supposed to be an heirloom piece and dumped it for this very reason. Very corny looking with the big, open bottom. Went with a Schott--also they are made in the USA (as opposed to China.) And at $500 or so, a great price. you don't want a leather jacket that screams "department store." Also have an Aero--check those out, too.
Black is the only way to go. White is corny, red would be cornier and don't do gray unless it's a monochromatic look you're going for. You didn't mention the color of the pants--others will want to know, too.
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.