Shoe Sole Upgrades
Living in a walking city like New York, you'll find yourself "going through" shoes at a much faster pace than normal. Add to that the wet and icy winter weather, and you may find that most shoes barely last the season.
My solution to this has been to upgrade the soles on all my shoe and boot shoes to "lugged" soles -- these are the classic rubber soles with knobby tread for lots of traction. You can have this done at any shoe repair store, and this inexpensive ($20-$40) upgrade with vastly extend the life of your soles.