Need My First Pair of High-End Shoes

Get a pair of dark brown brogues or a brown suede chukka boot.

buy a brown brogues, It's good for any ocassion, if you want more casual, brogues with wedge sole is also pretty nice..

are you looking for more of a dress shoe? 

I typically wear Tod's moccasins with jeans or Clark Desert Boots when I go out but I'm thinking it may be time to get some real shoes.
 

For a dress shoe i would suggest black first. But TBH i always wear brown now unless its with a suit, but even then i tend to go towards brown and brown suede. But if this helps your question i get more utility from my brown shoes.

Then brown. The black first advice comes with the presumption that you'll need them to be able to work in conservative environments like a job interview. Sounds like your life is much more casual, even in traditionally formal settings.

Dark brown brogues sound like an exellent choice, and yeah, they'll go with jeans. Khakis would be a good investment in any case, though. Traditional tan (or stone- they're interchangeable depending on which you like more) is the best color to start with, then medium gray. Then olive. Navy is way down the list for khakis, though I do have a pair.

really?

I find I wear my navy chinos more than all the rest

I too use my navy chinos more than the rest of the lot.

Yeah, I don't think I'd ever wear medium grey or olive chinos....definitely not before navy.

Navy chinos, walnut strands, light vneck over an interesting dress shirt=win

If you're willing to up your budget a bit and you're a size that's not that common, you may be able to find Ralph Lauren Darlton/Marlows (they keep switching names) at a digestible price.

You see black or grey suede moccasins is something id like to learn how to pull off while wearing a suit. I think its a great look if done right. I personally love the look of dark brown with jeans, and especially like tobacco suede with jeans. My advise to you is wear an outfit that you would wear to a "SF style hipster restaurant" and go to a department store and try on various pairs, if you are in need of new chinos/slacks then by all means get some but don't go out of your way to buy stuff to match a pair of shoes.

I'd suggest some oxfords/blucher mocs. They can go with most anything. Brown will be more versatile than black in a casual setting. The AE stuff is good as well if you have that budget.