The derby shoe deserves more attention than it typically gets largely because it’s been overshadowed by oxfords at the smarter end and loafers at the more casual end without people fully appreciating that it occupies a genuinely useful middle ground. The open lacing system which is what distinguishes a derby from an oxford makes it slightly more casual and also significantly more comfortable for people with wider feet. We’ve found dark brown or oxblood derby shoes to be one of the best investments in a shoe wardrobe because they go with suits and smart separates beautifully while also working with chinos and smart casual outfits in a way that doesn’t feel overdressed. A simple cap toe derby in good quality leather is the version we’d start with because the lack of decoration keeps it versatile across the widest range of situations.