K, you are asking the right questions, I think. This is exactly what I need to parse through.
I have, in the past, worn lots of olive green, because it does look good with my eye color. But I wind up pairing it with browns and autumn colors, which are okay but not my best and more importantly, expand my wardrobe to double the size. (Reference recent threads on seasons/colors... I am primarily a soft summer but can absolutely wear some other warm colors too... just no orange. No no no no to orange!).
That said, looking at this pic and my WiW from Saturday (navy dress with army jacket)... navy and olive look smashing to me. It's a nice way to dress down an outfit (something I often have trouble doing -- weekend casual is my hardest and most challenging capsule). I don't wear that army jacket very often but it's not because of the color; it's because the fabrication is so ... meh. Matte finish. This jacket had richer texture, so appealed to me more than I imagined it might. (Same as how I don't really like navy all that much, unless it's in a rich, non-flat/matte texture).
I have a lot of navy now (tops, jeans). I also have a lot of black. Would this jacket go over a black dress? Would it work with white? (Instead of khaki?) I also have a lot of grey, but I'm very tired of grey so I worry less about whether it would go with that. And yeah.. does it go with burgundy, purple, jewel tones, because I have a lot of that too... would it go, for example, with my cobalt wool coat? Because this jacket would have fit under my winter coats, easily.
I know a black leather jacket will go with everything. But, is black my best color, as I get nearer and nearer to 50? That is another great question. Sure, navy leather might be more flattering but what are the chances of me finding a perfect fitting navy leather jacket, when I haven't been able to find one in black? If petite offerings are going to be available (and it's height of season and I've seen... ZILCH... well, they will be in black. And that's it. I guarantee....