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When you’re the son of Matt Weiner, creator of the impeccably styled TV series "Mad Men", you’ve got serious sartorial standards to live up to. Arlo Weiner has been creating his own style since the age of three—when he asked his parents for a top hat. Soon he’d moved on to striped bow ties, crushed velvet jackets, madras pants, and ascots (yeah, he knows what an ascot is).

Arlo Weiner has become one of the sharpest, most original dressers this side of second grade. (Arlo on Dad’s show: “That’s where I’ve gotten a lot of my inspiration.”) His look is part Oliver Twist, part Royal Tenenbaums—eclectic and kidlike, but somehow knowingly so. (His favorite item right now: a fez. “I like to flick the string,” he says.) Even in L.A., a city where half the populace dresses to be noticed, Arlo stands out. A favorite story in the Weiner family is the time perma-cool rocker Beck followed Arlo down the street, so taken was he by the kid’s head-to-toe plaid.

Arlo, who plans to start designing his own clothes as soon as his mom gets a sewing machine, likes to mix and match bright colors and patterns. In fact, he’s up for trying just about anything—except sneakers and jeans. “They’re really not my thing,” he confesses.

Click men.style.com to see a slideshow of Arlo's hip style.