Boys Dept.

Mad Men Son More Fashionable Than You

From the sandbox to the Sartorialist: Eight-year-old Arlo Weiner is proof that a keen eye for fashion runs in the family. The son of Mad Men creator Matthew Weiner cruises to second grade in crushed black velvet pants, a top hat, loafers, and his dad’s old brown leather satchel. For the past five years the undeniably elegant boy has honed his look, which GQ describes as “part Oliver Twist, part Royal Tenenbaums.” Double bow ties and a cane borrowed from his grandpa—trust us, it works—complete his plaid-heavy ensembles that stray from the so-passé jeans and sneakers, which he calls "really not my thing.” The playground just became decades more fashion forward.