^Seems versatile in terms of colors, but not formality/types/style.
After thinking about it more and seeing some suggestions here's a modified 5:
1. Black captoe oxford
2. dark brown suede chukkas (or lighter colored, not sure)
3. Tan double monk cap toes
4. Color 8 wingtip boot (commando soles for inclement weather)
5. Medium brown captoe oxford