Compare Ichabod Crane and Rip Van Winkle in "The Legend of Sleepy Hollow" and "Rip Van Winkle" as images of manliness.
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Well, if it is images of manliness you are looking for, Ichabod Crane and Rip Van Winkle don't seem to present us with the kind of masculinity and power that we associate with the term. Note how Ichabod Crane is introduced in the introduction to "The Legend of Sleeply Hollow":
The cognomen of Crane was not inapplicable to his person. He was tall, but exceedingly lank, with narrow shoulders, long arms and legs, hands that dangled a mile out of his sleeves, feet that might have served for shovels, and his whole frame most loosely hung together.
His eccentric appearance coupled with the way that his presence makes people think of famine victims surely does not present him as a red-blooded male in the way that Brom Brones is presented. Certainly, it is not just his appearance that gives us this impression: the ease with which Brom Bones is able to trick Ichabod and scare him away shows that he is a weak-willed coward at best.
In the same way, Rip Van Winkle is presented as a man who is responsible and able to look after his family. The text shows that he is willing to work for anyone except for his own wife and family, and how his family suffer from this neglect as a result. He is shown to be a happy-go-lucky kind of figure who is incapable of asserting himself:
Rip Van Winkle, however, was one of those happy mortals of foolish, well-oiled dispositions who take the world easy, eat white bread or brown, whichever can be got with least thought or trouble, and would rather starve on a penny than work for a pound.
His unwillingness of improving his own position makes his wife and children suffer, and does not present a strong masculine image. In addition, the way in which he allows himself to be dominated by his wife and flees her regularly presents him as a weak, irresponsible man.
Thus it is that both of these characters are not presented in a way that allows us to associate them with traditional images of masculine strength and responsibility.