Jeffree Star's Transformation: Photos of the YouTuber Then and Now

Iconic, indeed. YouTuber Jeffree Star has been an internet celebrity for as long as we can remember — and he’s changed a lot along the way. We rounded up some photos so you can see his transformation from MySpace scene queen to high-fashion boss babe since he first stepped into the limelight in 2007.

Jeffree, born Jeffrey Lynn Steininger Jr., gained notoriety on the original social media platform in the early days of its popularity and everyone gravitated to his electro-pop music, whether you loved or hated it. He played small venues and tours in the U.S., as well as overseas, for a few years before releasing his debut album, Beauty Killer, in 2009.

The Los Angeles native signed to Akon‘s Konvict Muzik for his second album in 2010, but it was never produced due to creative differences. In 2013, Jeffree suddenly left the music industry, though it is unclear exactly what drove him to quit the business. However, he later said signing to Akon’s label was “the biggest mistake I’ve ever made.”

In 2014, the vlogger founded Jeffree Star Cosmetics, which has since grown into a multi-million-dollar business venture. Jeffree once claimed he invested his entire “life savings” to start the company — and now, according to Forbes, the brand is estimated to sell $100 million in product annually.

Aside from becoming a singer and a businessman, Jeffree was steadily growing his presence on YouTube. He started his channel in 2006, but it wasn’t until years later that it really blew up. To date, the makeup boss has amassed a whopping 17 million subscribers on the platform and his channel has nearly 2.5 billion views.

Jeffree has been pretty busy leveling up over the years — but he did find time for love for quite a while. He started dating skateboarder Nathan Schwandt in 2015 and the pair were inseparable for five years. The Michigan native moved out to Los Angeles to live with Jeffree and the pair parented five dogs together. They split in January 2020 and appeared to be on good terms despite the breakup.

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“Me and Nathan will be friends forever, I will always have love for him,” Jeffree said on YouTube while announcing the shocking split. “Are we in love with each other? No. But we love each other and he will always be in my life.”

Later that same year, Jeffree made a move to Wyoming after purchasing a 70-acre ranch and selling his famous pink Calabasas mansion.

Scroll through the gallery below to see Jeffree Star’s stunning transformation from scene kid to makeup mogul!