This is a very broad question and I'll answer it using the short story "A Clean, Well-Lighted Place." While this isn't the most obvious story to examine how Hemingway examines masculinity in his stories, the subtlety with which he looks at the ideas of masculinity through two waiters of different ages demonstrates his overall view.
In "A Clean, Well-Lighted Place," there are three men: an old, deaf man who tried to kill himself, an older waiter who has probably seen the horrors of war, and a younger waiter who has never seen war. The youngest of the men is full of vigor and detests the weakness of the old man, saying, "He should have killed himself last week." In fact, he adds to this idea by thrusting his manhood in front of the older waiter, saying he has "a wife waiting in bed" for him.
The older waiter...
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does not have as much confidence as the younger waiter. He had seen war—The Great War ended about a decade before this story was published. The older waiter says he "lacks" the youth and confidence the younger waiter possesses. However, the older waiter possesses the empathy the younger waiter lacks. Instead of wanting the old man to leave, the older waiter says, "Each night I am reluctant to close up because there may be some one who needs the café." This older waiter also possesses nihilistic tendencies, perhaps because of the war (or just because of life). Theclimax of the story comes when the waiter thinks of "The Lord's Prayer" and replaces most of the nouns with the word "nada," which is Spanish for "nothing."
With these two characters, Hemingway shows that as men age, they begin to lose the vigor and overconfidence that characterizes their masculinity in their youth. This idea is seen in many of his stories, particularly those that discuss a middle-aged man or a man returned from war who becomes less assured and more introspective the older he becomes.