imo, there were better options at the time you bought them from afpos. anyway.
it's something you buy when you're already in the two digitis territory. carry on.
Do you really like the (?)wood interspersed with the rubber in the heel and the contrast at the top of the sole? Looks weird to me. And from what I've seen of your wardrobe, I can't imagine it working with much you already have. A more straightforward chukka would probably be more versatile.
I say this with the best will in the world: you really need to decide what kind of look you want to create for yourself and then buy items consistent with that vision. Your purchases tend to run a fairly wide gamut of styles, which would be OK if you had the experience to mix & match them in a way that works well. For now, I would humbly suggest you don't quite look at clothes in a way that lets you achieve that result, so save yourself the effort of having to match items by starting off with a really clear vision of your end goal and restrict your purchases to that vision.
I'm not good at MC casual, but the advice above is not specific to that sub-genre, so I feel OK about posting it here.