This is a great thread all around. JR thanks for starting it.
Thank you. I'm sure I did ease up on him this summer and hand out $$ a little too freely w/o realilizing it immediately.
Hey, it happens -- I've let my 6 yo watch entirely too much TV in the past month and now I am paying for it as he transitions back into school and responsibility.

I think we are all guilty of backtracking from time to time. Luckily my default word is "No," (and what SHELLY said about starting when they are toddlers is SOOOOO true!! I've seen the evidence pro and con!) so he knows he can't get away with too much lip or grief. But the next week or two is going to be rough ...
JR here is something I read in this month's Money magazine. I can't find the link to it on their website but it is titled "Get Financially Fit for back to School." The first two points apply to your situation and are basically what you have heard here. But it always helps me to have "instructions" because emotions take over from time to time when they are your own kids and it is hard to be tough and see things clearly!
1) NEGOTIATE THE BUDGET.
Set Shopping Boundaries: Familes plan to spend an average of $527 this season on clothes, supplies and tech, 20 percent more than last year, according to the National Retail Federation and BIGresearch. To keep your own tab in check, take care of the essentials first, then give your teen a budget for extras and stick to it. She can decide whether to blow money on one pair of designer jeans -- or to buy three pairs of Levis.
Let your kid lead: Ask your teen to create a list of his weekly expenses such as lunch, gas and entertainment, then decide how much you will contribute. Again, leave the spending decisions to your kid. Overloading on snacks every day means the weekend movie may have to wait.
2) TEACH MONEY MANAGEMENT
Kick off a saving habit: Want your kid to learn to save? Carrie Schwab Pomerantz, president of the Charles Schwab Foundation, suggests requiring a high school student to stash at least 10 percent of any income in a savings account. By the time she gets that first paycheck after college, saving should be second nature.
Ease into plastic: A recent Schwab study confirmed that teens know plenty about spending money on debit and credit cards but little about maintaining a positive bank balance and adding up compound interest. Link a debit card to your teen's savings account as a training tool, and make sure he tracks his balance.