Then: With his straw fedora and boho-chic scarf, the chubby-cheeked 8-year-old looks oh-so adorable at the 2009 Invictus premiere with mom Angelina Jolie and dad Brad Pitt in Beverly Hills.
Now: He may be a few inches taller and a lot leaner, but the 12-year-old proves he still knows how to dress for the red carpet – this time in a dapper tux – to support his mom as she was honored at the Nov. 16 Governors Awards in L.A.
Then: Jennifer Connelly’s handsome 8-year-old was the perfect little gentleman when he accompanied the actress to a 2005 Fresh Air Fund event in New York City.
Now: The 16-year-old is a whole lot taller, but he still enjoys suiting up as mom’s red-carpet date, appearing with the actress at the Artwalk NY benefit at 82Mercer on Oct. 29.
Then: In October 2009, Jude Law’s 13-year-old eldest son with ex-wife Sadie Frost let dad take the lead around N.Y.C.
Now: The 17-year-old (here looking dapper at London’s Primrose Hill Festival on Sept. 8) is putting the looks (and confidence!) he inherited from dad to good use by starring in Tiger of Sweden’s latest campaign. “To be above the cut, you have to think a little different,” he declares in the brand’s video.
Then: To celebrate her first feature role, the 8-year-old hits the red carpet in a sweet crimson dress and long curly locks with dad Judd Apatow and mom Leslie Mann for the 2007 premiere of their comedy Knocked Up.
Now: The 14-year-old still looks sweet – but a lot more sophisticated – in a mixed floral-print ensemble at Teen Vogue‘s 11th annual Young Hollywood party Sept. 27. She’s also sharpened her comedic timing in two more of dad’s films, amassed almost 175,000 Twitter followers and created a blog where she muses on everything from her pets to the importance of reading The Catcher in the Rye.
ELLA BLEU TRAVOLTA
Then: Even at 9 years old, John Travolta and Kelly Preston’s only daughter seemed more than ready to glam up for a September 2009 Walt Disney Pictures event.
Now: Nearly three years later, she’s clearly played enough dress-up to develop her own personal (and tastefully edgy!) style, which stole the spotlight from Dad at a June N.Y.C. screening of his film Killing Season.
CALEB & LIV FREUNDLICH
Then: In 2008, 10-year-old Caleb was well below dad Bart Freundlich’s shoulders and 6-year-old Liv was still rocking girlie floral pants for a stroll with their parents in New York City.
Now: Cal, 15, has grown a few inches taller (he’s almost the same height as Dad!) and Liv, 11, strides stylishly in step with look-alike mom Julianne Moore in July.
Then: Here in November 2009, the baby-faced tween, 11, loved to match up with mom, former supermodel Christie Brinkley, at special events.
Now: The budding photographer, 15, still likes to hit the red carpet with Brinkley (they’re almost twins!), but now she’s a few inches taller, has her own Twitter page and has been featured in Teen Vogue.
Then: At 7-years-old, Teri Hatcher’s adorable tot came up to her mom’s hip and flashed a sweet grin before a 2005 performance of Chitty Chitty Bang Bang in New York.
Now: Fast-forward eight years, and the teen now struts her stuff alongside her famous mom, matching her inch for inch in height and donning a similarly casual cool ensemble during a June outing in L.A.
Then: Shortly after father Steve Irwin’s death, the bright-eyed 8-year-old stepped into the limelight with mom Terry and little brother Bob in 2007 to continue spreading Steve’s message about animal appreciation.
Now: Since then, Irwin, 14, has traded her family’s signature khakis for film roles and red carpets, including joining Russell Crowe at the June 24 Australia premiere of Man of Steel.
Then: The 12-year-old daughter of Uma Thurman and Ethan Hawke stayed in stride with her lookalike mom while grabbing ice cream during a 2011 visit to Paris’s Luxembourg Gardens.
Now: Nothing’s changed! At a Calvin Klein Collection Human Rights party in New York City on April 17, the 14-year-old proves she’s still the spitting image of her actress mom, hitting the red carpet in a chic dress and sporting long blonde locks.
Then: By the time she was 11 years old, there was no doubt that Reese Witherspoon and Ryan Phillippe’s daughter was tearing a page straight out of mom’s style book, stepping out in skinny jeans and work boots in 2011.
Now: But by October 2012, it was clear the 13-year-old was coming into her own, transitioning from mommy’s little lady to a cool Converse-rocking Cali girl.
JADEN & WILLOW SMITH
Then: Even when posing with their famous parents Will and Jada on the red carpet in 2010, the siblings always wowed fans with their supercute preteen charm.
Now: So it’s no surprise that Jaden, 14, and a hair-whipping Willow, 12, have since stepped into the spotlight with their own successful careers, from touring with Justin Bieber to starring in movies.
Then: While on her way to a 2004 Kabbalah service in N.Y.C., the gap-toothed (just like mom Madonna!) cutie, 8, displayed her love of color and glittery butterfly bows.
Now: Today, the mature 16-year-old is inching toward adulthood in darker hues.
Then: In 2010, father-daughter bonding for David and his little girl, 10½, meant taking in a Knicks game.
Now: Clearly, some things never change, as the twosome – including a more grown-up-looking Madelaine, now 13 – sit courtside to watch their fave team play in January 2013.
Then: Madonna and Guy Ritchie’s oldest son, here skiing at at 8½ with his dad in 2009, always exuded a cool demeanor.
Now: With a fuller face and shaggier hair, the almost-teen, now 12½, is hitting all the milestones of adolescence with a big smile – and braces.
Then: While filming in Toronto in 2010, Michelle Williams let her 4½-year-old daughter (she looks just like her dad, the late Heath Ledger!) lead the way.
Now: Three years later, the 7½ year-old trades in her jeans for a ladylike dress as she heads out Sept. 9 to help her mom celebrate her 33rd birthday in N.Y.C.
GRACIE, MAGGIE & AUDREY MCGRAW
DAVID RITCHIE & MERCY CICCONE
Then: It was double the trouble – and double the adorable! – for Madonna’s pint-size brood, who hung out at a Paris park while tagging along for the pop veteran’s 2009 Sticky & Sweet tour.
Now: Life’s a beach for the siblings, both 7, who are still growing up and hanging out together.