From Playground to Runway: The 50 Most Fashionable Kids

Confession: While at my parents’ house recently, I came across a pretty adorable photo of myself (in my opinion) as a wee tyke. It wasn’t that the towhead version of myself that melted my heart, it was the sick outfit my mother curated. I secretly envied the three-year-old version me in her ironic banana yellow sweater and patterned, rust-colored corduroy — why couldn’t I have that for my fall wardrobe?

It me thinking: What other kids’ style do I shamelessly envy? With designers from Oscar de la Renta to DVF releasing childrenswear lines this year and even street style blogs devoting themselves to stylish children, it seems that we should be taking notes from first graders rather than fashion editors.

With that in mind, we decided to share who we think are some of the most fashionable kids on the block from past and present, and even found some spectacular shots of some of Hollywood’s leading ladies and gents as young bucks. See them all in the slideshow above and be sure to give us your pick for most stylish tot in the comments section below!