Entertainment TV Celebrity Serenades, Tropical Getaways & More: A History of Kylie Jenner's Most Extravagant Birthday Parties From yachting in Italy to tropical getaways with her model besties, the now 22-year-old makeup mogul goes all out when it comes to celebrating her birthday in style (we're guessing our invite got lost in the mail??) By Sophie Dodd Published on August 10, 2019 02:40 PM Share Tweet Pin Email Trending Videos 01 of 11 Coming up Roses Kylie Jenner. Kylie Jenner/Instagram When you’re known for gifting luxury cars to your loved ones on their birthdays, it’s pretty clear that a classic bouquet just won’t do. Before jetting off to Italy to celebrate her 22nd birthday on a 300-ft. yacht with her family, Jenner came home to find her entire house covered in red roses, courtesy of boyfriend Travis Scott. The romantic gesture floored (ha) the makeup mogul, and their 18-month-old daughter Stormi seemed equally delighted by the slightly more expensive (and less practical) take on wall-to-wall carpeting. “This man covered my house in roses OMG!!!!!!!!” Jenner wrote over a video that showed off the impressive display on her Instagram Story. 02 of 11 Drinks on Me Kim Kardashian Instagram Cheers to 21 years! The makeup mogul officially hit America’s legal drinking age in 2018, and celebrated with a star-studded pink-themed bash at Delilah, a restaurant-lounge and celebrity hotspot in L.A. Her “Sicko Mode” rapper beau performed as she and her sisters — along with VIP pals like Bella Hadid, The Weeknd and Chris Brown — broke it down on the dance floor under a neon “21” sign. And lest her guests forget just who they were celebrating, drinks were served by staff wearing T-shirts with the birthday girl’s Forbes cover — you know, the one that reported she was the youngest-ever self-made billionaire — on the back. 03 of 11 Balling Out Kim Kardashian/Instagram Sisters Kim Kardashian West and Khloé Kardashian even kicked off their heels to jump around in the ball pit! 04 of 11 Sister Surprise Kim Kardashian Snapchat To welcome the youngest member of the KarJenner clan into her 20s, her mom and sisters surprised her with an epic 20th birthday bash. Some highlights of the evening included a voluptuous ice sculpture modeled after her famous figure, as well as a chocolate fountain, balloons that spelled out her name and a cake featuring a hilarious photo of the reality star. 05 of 11 Bae & Balloons Khloe Kardashian/Instagram Immediately upon entering her surprise party, Jenner made her way to boyfriend Scott to give him a hug. The pair, who had been dating for around four months at that point, had come from his concert with Kendrick Lamar at the Staples Center in L.A., and clearly he did a good job of keeping the secret on the way over! 06 of 11 Fun in the Sun Bella Hadid/Instagram The beachy birthday beauty rounded up her model besties for a tropical getaway to Turks and Caicos in 2016 to celebrate turning 19. Throughout the trip, she posted endless envy-inducing photos of her girl gang soaking up the sun and frolicking in the waves, set against a pristine backdrop of white sand and clear blue waters. 07 of 11 Squad Goals Justine Skye/Instagram All aboard the beauty boat! The Kylie Cosmetics founder was joined by a group of her closest pals at the time — some of whom are no longer part of her inner circle. Then-BFF Jordyn Woods was in attendance (years before the Tristan Thompson cheating scandal that ruptured their friendship), as well as Justine Skye (who dated Travis Scott before Jenner, and has since deleted the group photo from her Instagram), pals Bella Hadid, Anastasia Karanikolaou and big sister Kendall. 08 of 11 Legal Lady Kylie Jenner/Instagram To celebrate officially becoming an adult, Jenner kicked off the celebrations by rounding up her girl gang on the eve of her 18th birthday for a dinner party. 09 of 11 Hot Wheels SplashNews.com As if the birthday queen would leave it at a group dinner! For her extravagant 18th birthday bash at Bootsy Bellows nightclub in L.A., the star reportedly shelled out a cool $25k on the musical entertainment alone, treating guests to performances by Fetty Wap and a then-up-and-coming Post Malone. And while most of us would be lucky just to have our boyfriends remember our birthdays, her then-love Tyga went just one little step further than roses and a card when he gifted his girl a white Ferrari 482 Italia — valued at $320,000. 10 of 11 Cut the Cake Kylie Jenner/Instagram What more could a teen girl ask for than to be serenaded by The Biebs for her special day? Justin Bieber even gave Jenner a shout out on his Instagram to celebrate her 17th birthday. She replied in kind, thanking him for singing at her party — but fans were more focused on her thanking “T” for a lavish birthday cake, amidst speculation that she and rapper Tyga, then 24, were dating while she was underage. 11 of 11 How Sweet It Is Khloe Kardashian/Instagram Sweet 16!