As the above answers address, Willy has a mistaken sense of the American Dream. (Or the modern world has stream-lined and distorted the original "Puritan Work Ethic" into a sales pitch and quick buck.)
One aspect I would like to emphasize is this. Each generation would provide a life better for the one that follows. The modern interpretation of the American Dream involves getting the deal done at any cost. Willy gives stockings to the secretaries in order to be more productive, make more money to provide for the wife (for whom he can't afford to buy stockings.)
The infidelity falls into the same catagory, in a large part. It is a business gesture in order to provide. Biff's witness to this sheds light on the rationalization of Willy. He almost seems indignent enough to say, "Look kid, I did this for you and your mother! Can't you see that?"
Willy is left talking through this circular logic. In trying to create a better life for his sons, he destroys them.
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