Nordstrom Rack offers the Cole Haan Pebble Leather Backpack in Black, Tan, or Chocolate for $97.43 plus $7.95 for shipping. That's the lowest price we could find by $63. It features an exterior pocket.
REI offers the Bogs Men's Cruz Chelsea Rain Boots in Mocha or Black Olive for $66.83 with free shipping. That's $68 off list and the lowest total price we could find. They're available in select sizes from 8 to 14, although not in all size/color combinations.