Winterbourne, a character described as "addicted to observing and analyzing" the opposite sex, is actually more judgmental than observant, or analytical, as he likes to presume. If he were analytical, then he is not as sophisticated as he tries to come out. If he were a cosmopolitan man, he would have been able to understand Daisy, instead of crouching away from her in doubt. In not so many words, Winterbourne is one of those individuals who can only succeed within his own element; he is a product of his historical time and society. Therefore, it is likely that, as his society begins to crumble, so will he crumble with it.
I was booked to make a mistake. I have lived too long in foreign parts.
It is through the character of Winterbourne that the questions about Daisy's overall propriety arise. It is true that she is provincial, embarrassing, and inattentive to proper female behaviors, but, in the long run, her behavior is more realistic and true to the heart than that of Winterbourne.
Biased by a partiality towards puritanism, Winterbourne demonstrates to be a man who follows the mandates of society, just as they are without question.
Winterbourne had an old attachment for the little metropolis of Calvinism; he had been put to school there as a boy, and he had afterward gone to college there
That places him in a position of a follower, more than a leading man. Although he feels an attraction that sometimes leads him to try and understand Daisy, he is still unable to do so. This is because, far from analyzing her, his style is more to label and categorize Daisy (and every other woman) within a pre-conceived notion of who is who.
But this young girl was not a coquette in that sense; she was very unsophisticated; she was only a pretty American flirt. Winterbourne was almost grateful for having found the formula that applied to Miss Daisy Miller.
Like his name implies, Winterbourne is a cold and emotionally isolated man. This means that he prefers the propriety of following the rules of decorum to attending to the needs and wants of his life. In his behavior toward Daisy he seems condescending and appears to believe proud, conceited, and sure of his complete superiority of intellect and morals. Yet, although Daisy is not a completely likable character to some, it is fair to state that Winterbourne never gives Daisy a "chance" by trying to view her from a new and perhaps alternative point of view.