These days, a lot of little boys wear their baseball caps backwards. Sometimes this style is called 'Gang' or 'mechanic' style, though I do not see any preference for backwards pointing bills among street gang members and/or automechanics. In any case, the gangsta caps are typically pushed on the side rather than backwards. In Chicago, gangsta boys ought to have a do-rag under their caps; otherwise, it does not really count. My own idea is that little boys turn their caps around to advertize that they are boys (if you a girl sporting a ponytail, you cannot do it). Apparently, I am in a minority of one in this unorthodox view. The spectrum of opinion on the baseball caps worn around is very wide. There are three major theories, why they do it. I wonder which one is correct.
Catcher style; nothing serious
...The idea of wearing the cap backwards is commonly attributed to catchers in baseball, as when they began using facemasks, they had to turn the cap around to fit the mask on. (Wikipedia, http://en.wikipedia.org/wiki/Baseball_c
...it may have been outfielder Ken Griffey Jr. of the Seattle Mariners who first got children to turn their baseball caps around. http://www.capsandvisors.com/history_of
...For some reason unknown to me (fashion? political statement?) it is common nowadays for African-Americans to wear baseball caps catcher-style, with the bill to the back. We have two contradictory statements from England:'It's traditional Bash Street Kids, English schoolboy, turn your baseball cap backwards and fire kind of thing (Tom Wood)’ implying that wearing baseball caps backwards is as English as Bashing Street Kids, and "the redoubtable Prof. Trudgill went around annoying us Yanks by asking: Q: "What do you do to make a yank drop 50 degrees of intelligence?" A: Turn his baseball cap around backwards." implying that the English view wearing a hat backwards as a sign of stupidity. http://listserv.linguistlist.org/cgi-bi
Gangsta & rebellion symbolism
GANGSTA: Perhaps the most successful personal image marketed to this day. Millions upon millions of brainless youths have spent billions upon billions in order to look and pretend to be part of the 'Gangsta' crew. The standard uniform for a typical 'gangsta' includes: one silly looking giant baseball cap, worn any way except facing forward… http://www.urbandictionary.com/define.p
...a teenager in Lea County, NM was arrested. Police felt his backwards baseball cap was a "gang symbol" and ordered him off the county fairgrounds. When he tried to reenter the fairgrounds later in the day he was arrested for "criminal trespass". http://www.freeexpression.org/newsw
...LAPD Chief Darryl Gates is instructing his anti-gang taskforce that a baseball cap worn backwards is a possible sign of gang activity. http://teaching.arts.usyd.edu.au/histor
...many young boys will be seen wearing them backwards to flaunt their individualism and spirit of independence. http://www.thetranscript.com/column
...I am an elementary school principal and at 3 schools, a mix of urban and suburban kids, I absolutely ban the cap-turned-around-or-side-ways look. We tell the students that if they're going to wear a cap, wear it properly. One of my pet peeves is some guy about as long in the tooth as yours truly wearing not only a baseball cap but one turned askew. How utterly pathetic. http://www.tnr.com/blog/show_comments.m
...a black student named Marlon Morgan wearing a sideways baseball cap was arrested during his lunch period. Marlon attended Saguaro High School in Scottsdale, Arizona, which has a policy against hats turned sideways. The policy cites this manner of hat-wearing as 'disrespectful'. He was asked to turn it forward facing. Marlon refused, pointing to other white students around him who were doing the same thing. He was asked to go to the office, which he didn't. The police were called, he still refused to turn his hat around. By then he was drawing a crowd, so the decision was made to take him into custody to prevent... well, the article doesn't exactly say. A scene, probably. He was held for several hours and then released, and no charges against him were made. http://web.morons.org/article.jsp?id=47
...For a woman, a baseball cap worn backward used to be code for "I'm gay." Like the earrings in guys' left ears. http://www.2blowhards.com/archives/0023
Evolutionary psychology rationale
...First, you need to ask yourself what signals a male needs to transmit to a potential mate in order to advertise his suitability as a source of strong genetic material, more likely to survive than that of his competitor males. One answer is brute physical strength. Now, consider the baseball cap. Worn in the traditional style it offers protection against the sun and also the gaze of aggressive competitors. By turning the cap around, the male is signaling that he doesn’t need this protection: he is tough enough to face elements and the gaze of any who might threaten him. Second, inverting the cap is the gesture of non-conformity. Primates live in highly ordered social structures. Playing by the rules is considered essential. Turning the cap around shows that the male is above the rules that constrain his competitors and again signals that he has superior strength.
from Julian Baggini’s The Pig That Wants to Be Eaten: And Ninety Nine Other Thought Experiments (the US edition is available now)
Why do our kids wear their baseball caps backwards?
PS: The next in the baseball cap fashion is
...the baseball cap with the sunglasses on top. It’s almost like a uniform for some guys. You never see them wearing the sunglasses, they just sit on top of their caps. http://www.bombippy.com/archives/2005/0