He has graced the cover of tabloids and is adored by one of the world's most beautiful women. He is an heir to millions and haunted by the paparazzi. And he's still in diapers.
Sean Preston Federline -- the first child of pop sensation Britney Spears and her wannabe rapper husband, Kevin Federline -- is only 11 months old and has already received huge media attention. Last September his early delivery was the focus of the entertainment world. But his fall from grace did not take long.
This September Esquire magazine dubbed the infant the world's worst-dressed man. The tiny tot earned the dubious honor for daring to appear in public in a faux-fur puffy coat and a red and black tiger striped tank top.
Esquire's tongue-in-cheek article is not the first time the press has picked on the children of celebrities and politicians. Former first daughter Chelsea Clinton received much flak through her teen years for being gawky and badly dressed.
But this time some top style experts are aghast at the Esquire move, suggesting it's not a nice thing to do to a child.
Style writer and social commentator Rachel Weingarten, author of the new style guide "Hello Gorgeous," says she has "no problem teasing a celebrity -- a fully formed adult -- but even I think it's a little more than mean-spirited to have chosen a 1-year-old as the worst-dressed man."
According to Weingarten and other style mavens, a worst-dressed list is a carefully crafted queue. Nellie Sciutto, an actress and writer on "E!'s 101 Most Sensational Crimes of Fashion," says that actors and actresses will often purposefully don "out there" outfits to get press.
When it comes to putting people on a worst-dressed list, the press is "very careful about picking people who want to be on it," Sciutto said. "It's very rare that you get a big star and totally crush them."
As an example, both Weingarten and Sciutto point to actress Chloe Sevigny as a what-not-to-wear American icon, who has made wearing eccentric clothes her trademark. "It's actually not the worst thing to be on the worst-dressed list," said Weingarten.
But for kids, such criticism can be devastating. While Sean is too young to understand the press swirling around him, "It's something that can affect him later in life," said Dr. Bill Maier, vice-president and psychologist in residence at Focus on the Family in Colorado.
"It'll be harmful when he reaches school age," said Maier, "when he gets around peers who see things in the press and repeat them to him."
The solution, Maier claims, is found in parental reinforcement. "He'll need an environment at home and with peers that counteracts that criticism. Someone that says to him, 'We love you anyway -- don't listen to that stuff.'"
But Sean's mother, Britney Spears, has already received significant criticism about her parenting skills from the press. Due with her second child in October, Spears was spotted driving her car with her son on her lap, and changing his diaper on the floor of a Victoria's Secret.
"She's very young," said Sciutto. "She has a lot going on with her home and career ... and she's making some mistakes and could probably use some help. Needing help is not wrong."
All three experts agree that if celebrity parents really want to, they can keep their children out of the press and spare them any negative limelight.
Many parents -- like Demi Moore, who relocated in the mid-'90s to Idaho -- move their kids out of Hollywood or New York to help them grow up. Others stay in the big cities but let their children make their own choices about fame and fortune.
So, while the Esquire burn won't scar Sean today or tomorrow, such negative press might play a big role in his development as he grows up. It'll be up to Britney and Kevin to make sure their son and his on-the-way sibling are not seen in pastel news boy caps and checks.