When would it be appropriate to wear these shoes in black? What kind of pants would be all right? Would jeans be too much? I'm new to this whole "caring about how you look" thing. Basically, I'm a colorblind fashion newb who needs as much help as he can get.
I also have a pending post with an inserted pic with a different pair of shoes.
Basically, you should never wear black shoes with jeans. It simply looks awful. A black shoe like that would only be appropriate with wool trousers or gray and olive khakis- it's a fairly casual styling in a formal color, which is a really awkward pairing.
The fifth avenues that you just posted are a much better choice. Suits, wool trousers, gray or olive khakis. Again, no jeans, since they're still black. Get the same shoe in brown, and it could work with jeans, but that's a rather formal styling.
Basically, the only shoe that can really work all the way from jeans to suits are brown or burgundy wingtips. And those have their detractors on either end- some hate them with jeans, some hate them with suits. You might also be able to shoehorn a brown plaintoe monk into that category, but those stand out enough that they really should be worn as part of a wider shoe rotation.
IMO, you need two pairs of shoes- one pair of brown/burgundy in a more casual styling that can work with jeans up through wool trousers, and a fairly formal black pair that will see use with suits and jacket/trouser pairings. Of course, that's just the starting point.