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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4 Replies
jawntanamo_bae
jawntanamo_bae3mo ago
Personally, I’d go longwings especially if you’re looking for more casual
bishopcorrigan
bishopcorrigan3mo ago
Plain black captoes are just a miss for me in general, much prefer longwings
awburkey
awburkey3mo ago
Longwings but good Florsheim you’ll have to buy used
Angrymiddleagedjew
Used Florsheim longwings are absolutely god tier. For me, I get way more use out of my black wingtips than my solid black shoes.