Thank you for your enlightening response - I see my own thoughts did not stray too far from what you explained above: a shoe for grey tweeds, flannels and more roughly finished or country-inspired worsteds (herringbones) - therefore not a business shoe to wear with plain worsteds. A town shoe for leisure, perhaps where a brown town shoe would not accord with the colours of the suit and a plain or captoe black oxford would be too "formal" or business-like for the rest of the outfit.alden wrote: An oxford with tooling is best worn with city suits that have a bit of texture like flannels or worsted herringbones. The step down in crispness and clean lines goes along with the step down in formality. Think of Windsor wearing his suede shoes with chalked flannels. For men who wear tweed or tweed-like suits to town, a brogued oxford is a good way to go as well.
Perhaps there are other kinds of tooling that can be applied to a black oxford to make it less formal, that are less resemblant of the full brogue with its wingtip, such as this: