We're all for Toms' one to one, buy a pair, give a pair mission — but unfortunately, their standard offerings aren't going to do you much good when mother nature decides to dump five inches of snow on your doorstep. For those times, the Toms Botas Chukka Boot ($80) will do nicely, with a waxed canvas upper, wool felt lining, and a grippy rubber sole.
Own the trail in the New Balance MT101 ($75). This lightweight running shoe features a unique design to allow for a more natural run, a mesh upper for breathability, the Sure Lace system for added midfoot support, an Acteva midsole, and a built-in Rock Stop in the footbed to prevent your feet from being skewered by sharp rocks or other potentially painful objects. Of course, they're perfectly acceptable for kicking around town, as well.
If you're spending big money on a pair of shoes, you should at least try and keep them looking good. The Cole Haan Shoe Care Kit ($230) can help with that. It includes multiple brushes, a polishing cloth, and a fine-looking shoe horn, all encased in a handsome leather box with suede interior and piano hinge. Or you could just keep paying the shoe shine guy every day — it's up to you.