Joshua Goldman
Joshua Goldman
min read · October 18, 2025 · Entertainment

Diddy's Daughters Shine at Kylie Jenner's Starry Pop-Up After Father's Legal Troubles

Diddy 's daughters Jessie and D'lila Combs attended Kylie Jenner 's pop-up Kylie Cosmetics event in West Hollywood on Friday

Scandalous Dad, Diddy's Daughters, Jessie and D'lila Combs, Shine Bright at Kylie Jenner's Star-Studded Pop-Up Event

In a shocking turn of events, Diddy's twin daughters, Jessie and D'lila Combs, proved they're more than just their father's children. The 18-year-old sisters attended Kylie Jenner's highly anticipated pop-up event in West Hollywood on Friday, radiating confidence and glamour amidst the buzz surrounding their dad's recent sentencing.

The young women arrived in matching pink Body by Raven tracksuits, flashing megawatt smiles as they coordinated their wavy, waist-length hairstyles. The identical twins looked like they just stepped off a runway, with soft blush, mauve-toned lipstick, and brown lip liner accentuating their features. They even took to Instagram after the event, sharing a snapshot of their stunning diamond necklaces and matching bracelets, captioning it "King Kylie" - a nod to their idol's entrepreneurial spirit.

The 18-year-old twin sisters arrived in matching pink Body by Raven tracksuits

But what makes this story even juicier is that Diddy, real name Sean Combs, has been in custody since September 2024. With over four years left to serve on his sentence for racketeering conspiracy and transportation of prostitutes (although he was acquitted of sex trafficking), it's clear the twins are learning to navigate the complexities of their family life.

The sisters have been fiercely supporting their troubled father throughout his trial, with Diddy's mom passing away in 2018 due to natural causes. Their dad was convicted of two counts of transportation for prostitution, but acquitted on more serious charges. However, things took a dramatic turn when he was fined $500,000 by U.S. District Judge Arun Subramanian, who condemned his "savage" abuse of ex-girlfriend Cassie Ventura.

The verdict sparked outrage among fans and critics alike, with many questioning why Diddy wasn't held accountable for the more serious allegations. However, it's clear the twins are choosing to focus on their own lives and futures, rather than getting bogged down in the drama surrounding their family.

The young women, who share an Instagram account, took to the platform after the pop-up to share a snapshot showing off their diamond necklaces and matching bracelets

But they're not alone - Kylie's famous family was also in attendance at her 10-year anniversary event celebrating a decade of Kylie Cosmetics, which has made her a billionaire. Mom Kris Jenner, and sisters Kim Kardashian and Khloe Kardashian all stepped out in style to support the entrepreneur, along with other A-list stars like Hailey Bieber, model Gabbriette, and The 1975's Matty Healy.

Kylie launched her Kylie Lip Kits in November 2015, which marked the beginning of an empire that now includes fashion range Khy, vodka beverage Sprinter, and a cosmetics line worth hundreds of millions. It's clear she's come a long way from her humble beginnings as the youngest child of Kris Jenner and Caitlyn (formerly Bruce) Jenner.

As for Diddy, with his release date looming in November 2028, it's likely he'll be out of prison just in time to see his daughters blossom into young women. But will they still be able to forgive their dad for his past mistakes? Only time will tell.

The girls' outing comes weeks after their father, 55, was sentenced to 48 months in prison; pictured in 2018

Kylie's sister Kim Kardashian was also at her 10-year Kylie Cosmetics anniversary event to celebrate a decade of the business that made her a billionaire