I want to take a different position at answering this question.
I believe that the answer depends on the field/type/characteristic of jobs. However, since I have only been involved in a certain field, I can only speak for the field that I am familiar with.
If you look at traditional "white collar/elite" occupations such as lawyers, bankers, doctors, analysts, consultants, accountants, and etc., you must have a college degree. In addition, that will not even be sufficient nowadays. If you want to move up to become a big dog, a lot of the traditional "white collar" jobs now want to see MBA, MA/MS, PhD, JD, MD, CPA, CFA and what not.
On top of that, the prestige of schools matters as well. A lot of the top firms want to hire people from the top schools (perhaps, top 10, if not top 5). Some firms will not even interview students from the second-tier schools. The definition of being "elite" to these people is very narrow, and conservative. This definition is often associated with your alma mattar as well as the names of the previous companies that you worked with.
So if you want to be involved in these types of fields, college and graduate school degrees are crucial. Plus, you need to go to the top schools. For instance, to folks in these fields, Northwestern and Depaul are clearly not in the same league.
Having said this, however, I do not think that having a college or graduate degree will determine whether you will be successful or make a lot more money. I have met and seen many successful and wealthy people without such degrees. A lot of people around me at work would consider themselves to be not-yet successful, and not-yet financially stable.