Both Ichabod Crane and Rip Van Winkle run counter to traditional images of masculinity.
Crane is a tall, thin, creepy-looking man with giant feet and a small head. He is likened to a scarecrow and a figure of famine. He works as a schoolmaster and bullies the children with beatings, while he is all softness and kindness to the ladies.
Crane is superstitious and likes to hang with the women, especially to hear stories about local ghosts and witches. This tendency to like the older ladies and old wives' tales shows he has an effeminate side, especially as he is often frightened walking home after these visits.
Crane is contrasted to the very red-blooded, masculine Brom Bones, a muscular, hearty, robust, and charismatic prankster figure who leads a group of young men. Brom represents all the pragmatic masculinity that Crane does not.
Rip Van Winkle also lacks traditional masculinity in his happy-go-lucky, apathetic inability to provide for his family or take care of his farm. Like Crane, though without such a malevolent personality, he likes to help the ladies with small chores. He would rather be drifting around aimlessly, however, or talking over old news in front of the inn, than doing anything purposeful to improve his life.
Both characters represent what a new nation wanted to reject: apathy, superstition, and a backward-looking quality associated with Europeans. Irving is contributing to building the myth of the American character as hardy, pragmatic, resourceful, energetic, and robustly masculine. This is represented by the clever Brom, who outsmarts the nervous Crane and wins Katrina. In "Rip Van Winkle," it is represented by the younger males in the village (not by accident, Rip sleeps through the American Revolution) who are energetically involved in the elections. They are participants in nation-building, unlike the apathetic, Old-World Rip, who was content to let George III rule.