I almost called this thread essential shoes but thought better of it... Most of my purchases have been done when I knew very little about shoes so don't judge me! Currently I own: Old 1. John Brommel's black oxfords with plain toe with medallion. Possibly German, leather sole, possibly goodyear welted, barely worn and still stiff and relatively uncomfortable. 2. No name cheap medium brown plain toe derbies, leather imitation sole, very comfortable 3. Chocolate Hugo Boss flat sole mocs w rubber sole 4. Dark brown Clarks driving mocs w rubber sole 5. Cole Haan Air Yacht boat shoes - oiled suede New 6. Chestnut Meermin wingtip oxfords with double leather soles - new, still breaking them in 7. Burgundy Meermin chelsea - MTO, should receive them in April What would be the order of your next 3 pairs and why? I'm mid 30s, live in Europe and work in a small office where the dress code is smart casual. I mostly wear suits and combinations without a tie and casual on Fridays by choice. If possible include specific brands and models. I don't have a specific budget but 500 and above per pair is probably too much.