At the Cannes Film Festival this year, a controversy exploded. Naturally, it was about shoes. Allegedly, some female guests who arrived at films wearing flats were turned away and told their flat-bottomed shoes were not in keeping with the black-tie dress code.

Cannes contested the story, but it spread like wildfire. The press nicknamed it “Flatgate.” Rashida Jones called it “sexist”—why must women wear painful footwear while men loll around in loafers? Benicio del Toro agreed and vowed to wear heels to the Cannes premiere of his film, Sicario, in protest. (He then broke his vow because he couldn’t find heels in his size.)

The hullabaloo highlighted high heels’ odd place in our culture: women are often expected to wear them at formal occasions, but they’re also painful and—at least at first pass—hard to walk in. Deciding when and where to wear them is hard enough when you’re grown, but what about when you’ve never worn them before? Below, we talk to a style blogger, a podiatrist, and some real-life high-heel wearers to figure out just when tiny feet are ready for tall shoes.

How Do I Know If My Kid Is Ready?

Some questions to consider before you hit the stiletto store.

Does your kid want to wear high heels?

There are plenty of reasons why they might. Isa Giallorenzo, the style blogger behind Chicago Looks, said, “I love heels! I think they're amazing. They totally change the way you walk, your proportions. … I think it's worth [some] sacrifice.”

editor Lisa Farver agreed. “I think it's great to let your kids play dress up in whatever they want.”

If your kid doesn’t want to wear heels, though, everyone I talked to agreed: no need to impose. A dressy flat works for formal occasions, too (unless your kid is jetting off to Cannes).

Can your kid walk in heels?

If not, it might be time for some practice around the house. editor Kelly MacDowell said, “You don't want your kid tearing around the church banquet in heels. Hello, emergency room.”

Is looking good your kid’s number-one priority?

If so, talk to your kid about how fun is always more important than footwear. Isa said, regretfully, "I remember just suffering terribly through the night because of bad shoes, non-practical shoes. … [And] this happened more than once."

Lisa recalled a similar experience. “I wish I'd known that it was a bad idea to wear stiletto boots to an outdoor concert. If you can't be comfortable, you aren't going to enjoy the show. And people are really only looking at you because you're limping, not because you look sexy.”

Does your kid know which styles are most (and least) comfortable?

According to Chicago podiatrist Dr. Jeffrey J. Betman, comfort is all about the toes. Pointy-toed heels often have “very very narrow and shallow toe boxes,” which can cause nerve pain, tingling, hammertoe, and bunions. “Basically, picture your foot as a square peg trying to fit in a round hole.” Dr. Betman recommends square- or round-toed heels with deeper toe boxes for a more comfortable fit.

Does your kid know how to wear heels in a healthy way?

“Walking in high heels does stress the feet quite a bit, the knees and the lower back,” Dr. Betman said. However, there are a few ways to minimize the stress. First, don’t wear heels for more than few hours at a time. Dr. Betman recommended alternating them with gym shoes or flats—shoes that let your calves stretch and your toes spread out—even over the course of one day.

Also, to maximize your comfort in high heels, he suggested “custom-molded functional foot orthotics that support the arches and distribute the body weight more evenly.” (These especially make sense if you wear heels regularly.)

Does your kid know “heels” and “girly” aren’t synonymous?

“You don't need to wear heels to feel feminine,” Kelly said. She was a self-described “girly girl” as a kid, into pink, dresses, and “anything that made me feel more feminine.” Since then, though, she’s decided prioritizing comfort works better for her than prioritizing stereotypically girly looks. “As with anything else, you should only wear what you feel comfortable wearing.”

So What’s the Right Age to Wear Heels?

Isa said, basically, whenever your kid wants to wear them. “I wouldn't forbid her to wear heels. She'll learn for herself that it's hard.”

Lisa said as early as 14. “I think kids are old enough to wear high heels when they can tell the difference between society's expectations about fashion and their personal preferences about style. Sometimes that takes a lifetime!”

Dr. Betman said that with “very very occasional [wear], I don’t think it’s a problem at any age.”

Kelly said “I think a child is ready for heels when they're ready to act like somewhat of a grown-up. If they can handle saying "please," "thank you," "sir," "ma'am," and "How's your stock portfolio looking?" without being prompted by their parents—I'd guess around 9 or 10—they're probably ready [for a small heel].”

Photo illustration by Mark Mills, Groupon

Check out related reads:

What's the Right Age to Start Wearing Makeup?

Is 12 too young? 14? We asked makeup artists, parents, a teenager, and a high-school guidance counselor to weigh in.

Are Heels and Flip-Flops Always Bad For Your Feet? We Asked a Podiatrist.

Dr. Donna Hayes tells us how to know when shoes actually fit and which shoe she’d like to wish out of existence.