"The Royal Tenebaums" is such an excellent movie, and it's so stylized that every single character is a style icon in their own special way.
Margot Tenenbaum is my favorite, obviously, and I've written about her before, but I've come to realize that her brother/love interest (hmm... felt wrong writing that, watch the movie for an explanation, it's not as bad as it sounds) is also terribly stylish.
Being "stylish" to me doesn't mean being on-trend. It means having your own look and owning it (and that look being enjoyable and aesthetically pleasing). Richie Tenenbaum has this.
Sports coat, tennis head- and wrist-bands, shaggy hair, manly beard. You're pretty dreamy, Richie. Pretty dreamy indeed.