Dapper Gentleman
Maddox Jolie-Pitt looks all grown up in a sleek black tuxedo while attending the Governors Ball with parents Angelina Jolie and Brad Pitt at the Hollywood and Highland Center in Los Angeles.
Beanie Boy
The 12-year-old looks rocker cool in a black beanie, leather jacket, slim gray pants and checkered slip-on sneakers while arriving at LAX with his famous mama.
So Punk!
Maddox and his mom go for similar looks in black ensembles at LAX—we totally dig the skull sweatshirt and matching beanie!
Clean White Tee
The near-teenager steps out in a crisp white tee, blue jeans and his oft-worn checkered slip-ons.
Gray Day
Maddox, flanked by Brad, Angelina, and little bro Pax, goes for an all gray get-up—featuring a linen sport coat and knit beanie—at the London premiere of World War Z.
Blond Ambition
Maddox steps out in an oversized World War Z tee and comfy sweats while out with brother Pax in Woodland Hills, Calif.
Casual Cool
The cool kid steps out in a striped tee, gray track pants, platform sneakers and his signature aviator glasses while arriving at LAX with mom Angelina Jolie.
Military Man
So cute! A young Maddox is spotted in military pants and a comfy gray crew-neck while out shopping for toys in Houston.
Fedora Cool
Brad, Angelina, and Maddox make for a stylish trio—check Mad's fedora and dotted silk scarf—at the Invictus premiere in Beverly Hills.
Go Saints!
Maddox's black-stripe fedora makes another appearance at a Saints playoff game in New Orleans' Louisiana Superdome.
Band Tee
The then-tyke stepped out with Brad and Angelina wearing a gray-and-neon Black Sabbath tee with black shorts and Vans at a beach in Malibu, Calif.