The disclosure relates to determining thermal insulation levels of clothing a user should wear when traveling to a destination. To do this, a thermal insulation level of clothing worn by a user and levels worn by a crowd can be analyzed from images including the user or the crowd. A thermal sensitivity bias for the user can be determined by comparing those levels for similar locations. Environment data can then be collected for the destination. A thermal insulation level of clothing worn by the crowd for the destination can be predicted based on the environment data. This level can be adjusted with the bias for the user to generate a thermal insulation level of clothing to be worn by the user at the destination. An image having clothing with that level can be displayed to recommend a style of clothing for the user to wear at the destination.