Education as means for self-improvement
Dick, a homeless bootblack, recognizes that other boys and men have better opportunities than he has due to their ability to read and write. He cultivates the friendship of Henry Fosdick, a young man about his age who has had some education. By bartering accommodation for tutoring, Dick is able to educate himself. The boys also go out of their way to attend Sunday school with Mr. Greyson, an adult man with a family of his own who takes an interest in Dick and considers himself a mentor.
At two points in the novel, Henry and Dick are judged based on the quality of their handwriting. Henry, who is competing with other boys for a chance to work in a shop, receives a timely character reference from Mr. Greyson but is not accepted as a shopboy until he shows that his handwriting is neat and well befitting a clerk. Dick likewise must show an example of his handwriting before Mr. Rockwell employs him in his counting-room as a clerk.
Clothing as a path to class acceptance
Twice during the novel, Dick receives a suit of clothing as a gift or as partial compensation for a good deed done for someone else. The first time, he notices that he and the young boy he is escorting around town are treated much better than he is usually treated by shopkeepers, vendors, and waiters. Even a stockbroker mistakes him for a young man with assets, as opposed to a homeless bootblack. This taste of respectability is one of the things that gives Dick the desire to rise in the world.
Near the end of the story, after Dick rescues Mr. Rockwell's son from drowning, Mr. Rockwell gives him a suit of even nicer clothing as partial reward. It causes him to fit in perfectly at the counting-room of Mr. Rockwell's business. The ten-dollar starting wage, much higher than the three-dollar starting wage of a shop boy, is indicative of a higher social standing.
Money
One of the things that sets Dick apart from some of the other boys is his desire to work hard for what he wants. He earns more than most bootblacks because of his outgoing "sales" personality and his willingness to put in long hours. However, initially Dick's standard of living does not reflect his work ethic. At the start of the story, the homeless Dick has no regular lodgings and very ragged clothing since he spends all his earnings at the Bowery Theater and by smoking cigars and treating his friends to oysters. Over the course of the novel his habits change to become more consistent with the middle class. He and Henry no longer go out at night or spend money at the theater, but Dick spends money on a basic room instead so the two boys have a relatively safe place to sleep and to store their belongings. The boys also open bank accounts and begin to save money. They spend, occasionally, on new clothing that will help them get a job (in the case of Henry Fosdick) or that will help them do good deeds for others, but for the most part they live frugal lives. This results in slow but steady accumulation of wealth.
From time to time Dick receives a windfall: a large tip, a gift of money, or some other gift such as clothing. At first, other people try to cheat him out of it, however the streetwise Dick is able to avoid being conned out of his money due to his intelligence and cunning. Dick also notices that "respectable" people are less likely to be falsely accused of theft. Eventually, Dick himself acquires enough of a reputation to be the one who is believed when a neighbor steals his bank account and tries to fraudulently make off with Dick's savings.
