John T. Rogers, age 26, grew up in rural West Texas, raised by a single mother who often worked three jobs to make ends meet. He says his 59-year-old mother remains fiscally conservative, refusing to spend a dime on herself, though she now earns a respectable income. But when it comes to spending, Rogers is not following in her footsteps. "Not to knock J.C. Penney's, but I definitely wanted to step up my style," he said. Earning $46,000 a year as a communications manager for a private, non-profit university in Denver hasn't held him back. He bought a hybrid Lexus...