Barely three months after he plunked down $13.6 million for a rakish contemporary mansion in the Hollywood Hills, Ryan O’Connor has done it once again. This time, he’s back out in the seaside celebrity enclave of Malibu, where records reveal the 33-year-old streetwear tycoon has splashed out another $10.4 million on an “architectural marvel,” per the listing. Completed in 1975 but rebuilt in the mid-’90s, the redwood-slathered structure sits right atop the sand, with unobstructed ocean views from Point Dume to Catalina Island.
Born and raised in Orlando, O’Connor grew up skating — a lifestyle that would serve as the basis for RipNDip, the apparel brand he founded in 2009. The bootstrapped company struggled until about six years ago, until social media gave O’Connor its proverbial blessing: an image of RipNDip’s feline mascot Lord Nermal went viral, and the rest is history. Today, the brand is one of the nation’s hottest hypebeast/streetwear labels, and has its headquarters on L.A.’s fashion-forward Fairfax Avenue — right next door to the West Coast outpost of Supreme, O’Connor’s main competitor. RipNDip is also known for its collaborations with other trendy brands like Teddy Fresh, the colorful apparel company founded by veteran YouTubers Ethan and Hila Klein.
O’Connor’s new Malibu property lies within a guard-gated community known for its popularity with celebrities. Some of his nearest new neighbors include Halle Berry and Sandra Bullock, who owns two multimillion-dollar homes within the enclave.
Astute real estate watchers will recall this is not O’Connor’s first Malibu purchase. Barely a year ago, the avid real estate lover paid $8.2 million for another oceanfront home along Malibu’s exclusive Broad Beach, though that property was flipped just a few months later — for a whopping $12.3 million — to his next-door neighbor, billionaire Behdad Eghbali. And the entrepreneur still owns a second multimillion-dollar property in the Hollywood Hills, this one a Streamline Moderne-style villa.