I tend to dress my island rep in an outfit that corresponds to the real-life weather, unless the in-game weather seriously conflicts. (If it's 60 here and snowing in game, I'll put on a virtual sweater and pants.) I know lots of players stick with the same handful of outfits year-round, but I feel responsible to ensure Ballad is comfortable in all the temperatures! I change clothes whenever I start up the game and I always wear shorts and t-shirts in summer, pants and sweaters with a hat in winter, and then for fall and spring I tend to match the (variable, Midwestern) weather I'm experiencing in real life.