Slips and falls and associated outdoor injuries are prevalent in cold climates. The objectives of this field investigation were to describe the consequences of slips and falls on ice and snow and the associated injuries, to assess the risks of various icy and snowy surfaces, to identify design needs of footwear, and to ascertain preventive measure preferences of outdoor workers. The organizations investigated were a newspaper delivery service, a military regiment, mining and construction industries. The results showed that fall events occur most frequently on ice covered with snow. This is due to the difficulty of perceiving hidden risks in order to adjust gait strategies. The professional footwear provided does not provide enough protection against slips and falls. Slip resistant properties are ranked as one of the top requirements by the users. Their most preferred preventive measures are footwear with anti-slip properties and the application of anti-slip materials, such as sand or salt.