1) A gelded feminized male who believes his elitist position in the world, as well as his privileged life makes him the authority on everything.
2) One who believes he is higher and mightier than the rest based on how much his parents spent on his college education.
The word is mostly used as an insult by real men (even those with a college education) to differentiate between themselves and the castrati.
Vinny: You got a problem College Boy?
Wesley: No, but I am smarter and richer than you.
Vinny: Really College Boy? Then why do I get more trim than you do?
Wesley: What is trim?
Vinny: Exactly my point, College Boy!!!
Term of derision generally used by uneducated individuals. Usually is intended to imply that the subject of the insult is a "sissy" or an "egghead."
This of course is merely indicative of envy on the part of the individual using the insult.
Schmuck: "Man, look at that punk-ass college boy. What a pansy, he thinks he knows so much."
College Boy: "Man, look at that schmuck. It must suck to work so hard for so little money. He should have gone to college
Dressing as a college student with a hip hop twist.
Kanye West dresses college boy