"To some extent, these are children being treated like poodles," he said.
Mass merchandisers and baby boutiques cater to that parental pride, and sometimes take advantage of it, he said. For example, baby shirts emblazoned with the logos of rock bands from the '70s and '80s say more about the parent than the child.
"They're selling an idea to a parent that says 'My child is cool; I'm cool. I'm much older, but I haven't lost it. I'm still just as happening as I was before," he said.
Encouraging the sort of "Zoolander" affectations in kids is as easy as laughing at them or taking their picture. It teaches children that they get attention if they act that way, Everhart said. Often that's a completely unconscious exercise, for parent and child, he said. After all, it's not unusual for children to emulate what they see in pop culture.
"Every generation recreates its pop idols," he said, "and much of what we see in youth culture is a response to the adult world."
But playing dress-up, after all, is one way toddlers learn about self-expression, Beveridge pointed out.
"We all know that toddlers can be extremely opinionated, so with these well-dressed kids, it begs the question of who's in charge," she said.
"I think we like to imagine both scenarios: Maniacal parents forcing this on their kids, as well as headstrong kids throwing a tantrum because they really, really want that Armani jacket."
There is something a little strange about just how much sass her 4-year-old daughter can show, said Samersova, the Planet Awesome Kid blogger.
"When I turn a camera on her, she automatically goes into some kind of weird, funky, funny pose," she said.
But don't feel too bad if you've done your fair share of spamming Facebook or Instagram with your child's personal fashion show.
A photo of a kid with swagger isn't necessarily creepy, or bratty or parental pride gone wild.
"It comes from, 'Oh my God, that dress is so cute on my daughter,'" Samersova said. "It doesn't have to be any deeper than that."