What does Winterbourne's efforts to understand Daisy reflect about his personality in "Daisy Miller"?

Appropriately named, the cold and calculating character of Winterbourne is the epitome of what, in the 21st century, we would call a kind of "hipster".  He has designed his life to play the part of the dandy, the society man, and the connoisseur of everything. While Winterbourne is quite a heavy character to digest, personality wise, it is through his dynamics with Daisy Miller that we realize the extent to which this man is willing...

Appropriately named, the cold and calculating character of Winterbourne is the epitome of what, in the 21st century, we would call a kind of "hipster".  He has designed his life to play the part of the dandy, the society man, and the connoisseur of everything. While Winterbourne is quite a heavy character to digest, personality wise, it is through his dynamics with Daisy Miller that we realize the extent to which this man is willing to give up his happiness for the sake of keeping up with his social masks. 

In reality, Winterbourne is quite fond of Daisy. Deep inside, the reader can tell that he must have been somewhat jealous of the fact that this girl gets to experience life to the fullest, without any fears of being called out by her peers.

Miss Daisy Miller looked extremely innocent. Some people had told [Winterboure] that, after all, American girls were exceedingly innocent; and others had told him that, after all, they were not. He was inclined to think Miss Daisy Miller was a flirt—a pretty American flirt. He had never, as yet, had any relations with young ladies of this category.

He is curious about this American girl. He is also definitely attracted, to a point, and for someone who lives to look "cool", Winterbourne would have caused a sensation with a young American gal.

Still, while he wants to join in the fun, he cannot get over the social mantras that he grew up with, and which are expected of him to fulfill. It is, in the end, easier for him to suppress his emotions and revert back to the annoying person that he is, than risk his reputation, nay, his status, for the sake of carrying on with someone who is, by all accounts, a naive "nouveau riche". 

Hence, his efforts to understand Daisy denote that there is an interest on his part of getting to know this girl at a deeper level. He does appreciate her joie de vivre, and he may look condescending in his treatment of her, but he is a product of his society: All that he can do is look from the outside in, and wonder about this interesting and strange creature named Daisy.