Earnestness comes from the core, whereas being hip or cool is all about trying to impress from the surface. The perfect example of earnestness to Randy is being an Eagle Scout. Whenever he’s interviewing people and learns that they were an eagle scout, he tries to hire them, because he knows there has “to be an earnestness about him that outweighed any superficial urges toward hipness.” Fashion, Randy adds, is “commerce masquerading as hip.” That’s why he rarely buys new clothes—his parents taught him that you should buy new clothes when the old ones wear out. So, though Randy’s wardrobe is far from hip, it’s kind of earnest, and that’s going to carry him through just fine.
Randy sees wardrobe as an extension of your attitude—rather than trying to be trendy and cool, Randy believes you should be practical and earnest. As such, he wears all of his articles of clothing until they wear out.