Genre I'd say it's a romantic comedy, not quite sure
Time Period and Origin I guess, it was made between 1995 and 2000; extended range of 1990-2002, but I'm certain it isn't earlier than 1980 or later than 2006. Fairly sure it's an american movie.
Setting A modern, big city setting (I want to say New York or London, but not sure)
Characters I remember the main characters quite well. The protagonist is a geek, who just came to the city for a job or school, he sticks out like a sore thumb, because he wears a warm woolen hat all the time. Similar to this:
The female lead is a red-haired woman, maybe early twenties or late teens, who has a goth-vibe about her.
Plot The plot revolves around the female lead helping the protaganist get his footing in the city, I'm pretty sure a romance blossoms between the two, but can't remember anything of the latter half of the movie.
Extra info The one thing I clearly remember is a scene, where the female lead asks the protagonist, why he is wearing such a silly hat all the time and he responds, it's because the body loses most of its heat through the head, which is why he wants to keep it warm.