Angelina Jolie’s eldest son, Maddox Jolie-Pitt, officially became a college student back in 2019—and yes, we felt the emotional weight of that milestone right alongside her.
The Hollywood icon was spotted in Seoul, South Korea, lovingly dropping off 18-year-old Maddox as he began his studies at Yonsei University. In a heartfelt video from the day, the then-44-year-old actress admitted she was doing her best to hold back tears. A major parenting moment—and a reminder that time truly flies.
We know—it’s hard to believe. Angelina and Brad have a college-age son? Where did the time go?
Naturally, we’re marking the moment the only way we know how—by looking back through the lens of fabulous footwear. From red carpets to everyday outings, let’s revisit some of Angie and Maddox’s most precious (and stylish!) fashion moments together.
1. Angelina Jolie Turns School Pickup into a Runway Moment in Knee-High Black Boots
School runs never looked this sexy. Angie, dressed in a tight-fitting LBD and sleek, black-suede knee-high boots, caused a commotion just by picking up a then 6-year-old Maddox from the Lycée Français School in NYC.
Angelina Jolie turns a school pickup into a runway moment in a sleek black dress and knee-high suede boots while picking up Maddox from NYC’s Lycée Français on October 5, 2007 (Credit: WENN)
2. Twinning in Style: Angelina and Maddox Rock Matching All-Black Looks With Louboutin Boots
Almost a teenager, 12-year-old Maddox started showing his rebellious teenage streak in a skull-printed beanie and hoodie.
To show she still supports him as his mother, Angie twinned with her burgeoning teen in a similar all-black outfit: a bell-sleeved sweatshirt, leather leggings, and Christian Louboutin boots.
Angelina Jolie and Maddox nail edgy airport style in matching all-black outfits, with Angelina turning heads in leather leggings and iconic Christian Louboutin knee-high boots at LAX on April 13, 2013 (Credit: WENN)
3. Red Carpet Royalty: Angelina Jolie in Saint Laurent Mary Janes and Maddox in Sleek Suit at Maleficent Premiere
Angie was in her element in a Versace black-leather strapless gown and Saint Laurent ‘Janis’ Mary-Janes at the Maleficent premiere in 2014.
Angelina Jolie stuns in a custom black leather Versace strapless gown paired with Saint Laurent ‘Janis’ Mary Jane pumps at the Maleficent world premiere in Hollywood (Credit: WENN)
Maddox, by then, felt confident enough to go on the red carpet alone and posed for the cameras in his dapper gray suit and black horsebit loafers.
Maddox Chivan Jolie-Pitt makes a confident solo appearance in a sharp gray suit and classic black horsebit loafers at the Maleficent world premiere at El Capitan Theatre in Hollywood on May 28, 2014 (Credit: WENN)
4. Family in Fashion: Jolie-Pitts Make a Unified Statement in All-Black Looks at Unbroken Premiere
Angie, in her signature all-black ensemble, graced the Unbroken Berlin photocall in a Hugo Boss turtleneck top, Michael Kors tailored pants, and Balmain tortoise-shell-heeled zip sandals.
Angelina Jolie keeps it sleek and sophisticated in a black Hugo Boss turtleneck and tailored trousers, elevated by Balmain tortoiseshell-heel sandals at the Unbroken photocall in Berlin on November 27, 2014 (Credit: WENN)
A couple of weeks later, at the Unbroken LA premiere, the rest of the Jolie-Pitt clan showed solidarity with their mom in adorable matching all-black suits and ties.
Brad Pitt and children (from L to R) Pax Thien, Shiloh Nouvel, and Maddox Chivan at the Unbroken premiere at the Dolby Theatre in Los Angeles, California, on December 15, 2014 (Credit: WENN)
5. Glamorous in Saint Laurent: Angelina with Maddox and Pax’s Contrasting Styles at TIFF
Angie was lovely in a Ralph & Russo one-shoulder bow dress and Saint Laurent ‘Paris’ pumps at the 42nd Toronto Film Festival.
She was joined on the red carpet by her two eldest sons, Maddox and Pax, who looked like they disagreed on the dress code. Maddox was casual in black suspendered harem pants and white slip-on sneakers, while Pax was dapper in a blue suit and brown oxfords.
Angelina Jolie radiates elegance in a one-shoulder Ralph & Russo bow dress and Saint Laurent ‘Paris’ pumps, joined by sons Maddox and Pax—each showing off their unique style—at the First They Killed My Father premiere during TIFF on September 11, 2017 (Credit: WENN)
6. Angelina Jolie Channels Parisian Elegance with All Six Kids in Chic Family Outing
Angelina looked like the most chic Mother Goose as she walked around Paris with her six children trailing behind her.
Angelina Jolie with her children Shiloh Nouvel, Vivienne Marcheline, Maddox Chivan, Pax Thien, Zahara Marley, and Knox Leon (Credit: WENN)
For that no-doubt paparazzi-filled day, Angie was regally dressed in an Elie Saab caped coat, Fendi sunglasses, a Salvatore Ferragamo handbag, and Giuseppe Zanotti ‘Anette’ pumps.
Angelina Jolie wearing an Elie Saab caped coat and Giuseppe Zanotti ‘Anette’ pumps to visit the Louvre in Paris, France, on January 30, 2018 (Credit: WENN)
For readers interested in Angelina Jolie and her son Maddox’s more recent appearances, we recommend our article about their attendance at President Biden’s Republic of Korea State Dinner in April 2023. The piece highlights their elegant fashion choices and provides insights into their ongoing connection with South Korea.