Do you love buying shoes? Are you someone for whom shoe-shopping begets a Zennish euphoria? Yes?

Here’s some advice for you: Don’t do it with a 12-year-old.

My 8th-grade-bound son has long coveted classic Converse low-tops. Last week, we found a pair of lookalikes on sale for \$15. Sweet! “We’ll take ’em,” I bellowed, relishing the rare and unparalleled near-delirium of buying fabulous shoes at ridiculous prices.

“Um,” my son muttered sheepishly, staring at another pair of shoes: The Converse brand. All Star Chuck Taylors. Same color. Same style. Forty-five bleepin’ bucks. “I’d rather have the real ones.”

In my mind, I said this: “Well, I’d rather have a ’57 Chevy Bel Air convertible, yet somehow we’re leaving here in a dinged-up Honda.” But sensing that we were heading into tricky parenting territory, I uttered this instead: “But … they cost three times as much.”

“Yeah,” he said, forcing himself to meet my puzzled gaze.

“And they look … exactly the same.”

“Not exactly,” he explained. “These have a label.”

I had several problems with this situation. First, when pressed, my normally articulate child could not put into words why the brand mattered so much. His stuttered attempt contained the phrases: “important to me,” “make fun,” and, of course, “cool.”

I have specific words for people who would spend the cost of an annual subscription to both The Atlantic and Vanity Fair on sneakers that will be dragged from moving skateboards and will become too small for their wearer within four months. “Cool” is not one of those words.

But looking into my son’s almost-apologetic face, I suddenly remembered what it felt like to be, well, in his shoes. The brands were Izod, Guess, and Vans back then (dear god, do you remember LeSportsac?), but the desperation for “cool” was the same. The urgent desire to identify with a tribe, to demonstrate an understanding of what’s “right now,” to be conversant in the shorthand of a subculture, and to collect — and just as quickly discard — each of its brief badges of coolness.

As a parent, though, I wasn’t sure whether this was one of those moments wherein I should be the “supportive” mom (“Sure, honey, I know how important it is to fit in. Let me just cancel my dentist appointment next week so we can pay for these …”) or the “instructive” mom (“Let’s take a reality-check stroll outside and have a good look at the homeless fellow on the corner. Notice he has no shoes whatsoever.”) I don’t like either of those moms.

Psychologist John Duffy, author of The Available Parent: Radical Optimism for Raising Teens and Tweens, says there’s a better way to handle label cravers: Give them the opportunity to buy the stuff themselves.

“I encourage parents with brand-lusting kids to get their child truly invested, if that’s what they want,” he says. “For instance, ‘Yes, you can absolutely have that … Abercrombie shirt. Just let me know how you plan to pay for it.'”

Parenting coach Tina Feigal, who’s raised three brand-conscious boys, advises giving kids a clothing budget and letting them make their own decisions about how to spend it — without interjecting our opinions along the way.

“If they still want something and the money is gone, that’s excellent learning,” she says. “Don’t rob them of it by advancing their allowance.”

I got lucky with my son this time. He settled for the $15 knockoffs because after all our back-and-forth, they didn’t have the real Converse in his size and he didn’t want to leave with nothing. So parents, add this tidbit to your toolbox for handling brand-smitten kids: There’s only one thing more repellent to the adolescent brain than frugal spending habits; it’s delayed gratification.