I have a friend who hates lace-up shoes and wants to only wear loafers. He just got an office job where he should wear a suit most days, and asked for my assistance in buying some footwear to go with it. I offered a very basic black captoe oxford, and he rejected it, saying he hated wearing laced-up shoes and wanted me to go find some variations on loafers. I can't tell him "You normally shouldn't wear loafers with a suit" because that just makes him defiant - quoting rules doesn't work. It also doesn't work to just say, "It looks wrong," as I need to explain why. So how do I convince him to give some oxfords/derbys/anything laced up a shot*? Suggestions? * I realize that I haven't tried monkstraps or chelseas with him yet. But he needs a proper shoe wardrobe, and I can't omit all laced-up shoes.