Black Shoe Battle: Derbies vs Longwings

I'm currently trying to be more of the casual end of my business casual style, however, I noticed that I need a black shoe for my office. Seeing that even if I'm in a banking office, luckily, the dress code isn't as formal as it should be (I could see some wearing shirts and those Cole Haan Lunargrands and get away with it), hence me opting for either a derby/blucher that is slightly chunky vs a longwing.

I've narrowed my choices to two models, namely the Sanders Military Derbies and the vintage Florsheim Kenmoors. Between the two, which would see more wear considering my most casual get-up would be an Ametora take on workwear?
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