Any help appreciated.
@ Cabana Boy-
Depending on how some things fit you off the rack, I would recommend going Made to measure/ semi bespoke for your suits. Start with the navy, as you said, with a medium grey as your next one. From there, dabble in shadow plaids as they are also easily broken up. With a MTM suit you are really barely getting a price bump after buying a decent suit and having it tailored as it is.
I would suggest Reda or Vitale Barberis Canonico to get you started. You will get a lot of bang for your buck there. In NYC those are usually around $800, and my favorites at Aksel Bespoke do Holland & Sherry at $890.
As for shoes, I would send you to meermin before allen edmonds. check out the thread on them, everyone has been really pleased and they are of the same or better quality as AE, with a much more stylish shape and finish to them, and a slightly lower price.
Shirts- also go MTM. there's a big thread on moderntailor.com, which can be squirrely on their quality control but once you get it down they have great prices. You'll pay $50-$60 for a shirt regardless or more, and as long as you get the two ply you should be golden.
PM me if you would like for me to get into it further.