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It seems to me that grey is a prominent neutral in you wardrobe so olive would work well. The olive of the boots looks like it has a grey/green look on my monitor too.
I told myself military green is perfect for UWP when I ordered my Ash sneaks. I think it depends how bright the green is. If it's like an olive drab IRL as it is in the pics, I think it's great and will keep a long leg line with both black and gray bottoms.
