• Black oxfords: They should have minimal ornamentation like perforations, seams, wingtips, etc. You need a shoe that you can wear to a job interview, funeral, or some other event that requires seriousness on your part, and this is it. Pair them with your grey or black slacks or suits and make sure they’re leather-soled.
  • Brown dress shoes: Try a medium shade, like a tobacco color. You can wear it all year round and it looks excellent with blue, grey, and tan suits or dress pants. Try a wingtip, cap-toe, or dress loafer to start, also with a leather sole.
  • Brown casual shoes: These can be a rubber-soled slip-on or lace-up in whatever shade you like. Get a couple of different shades and styles so you can rotate them and not wear them out too quickly and throw them on with jeans or your khakis.
  • Boat shoes: These are great for sockless wear in the warm weather and are a great chance to throw some color into your shoe collection. Find a pair in blue, red, green, cream, brown, or whatever you like that’s available. Wear them with lightweight cotton pants or shorts in the summertime.
  • Non-athletic sneakers: No Nike Shox and no New Balances, I don’t care what J.Crew is offering. You can get a streamlined “sport-inspired” sneaker at very low cost if you look in the right places. Wear these with jeans when you’re hung over at brunch on a Sunday.
  • Snow boots: It sucks when your feet get cold and wet, no matter how grown up you are.

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