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Taylor Swift’s 5 most expensive items. You’ll never guess the third one. Number 5: Designer accessories and clothing. She owns exclusive items like a Christian Louboutin backpack and clothes worth over $3,000. She loves brands like Elie Saab, J.Mendel, and Versace, but she also gives new and talented designers a chance, like Michelle Smith during her first world tour. Worth? $700,000. In her garage, you’ll find models like the Porsche 911, a Mercedes Benz Viano, and an estimated Audi R8. The most expensive item is the Toyota Sequoia. Worth $1.2 million. Number 3: Leg insurance. Like many other artists, she took out insurance to protect her legs. She thought the insurance company would value her legs at $1 million. However, they ended up being worth an astronomical $40 million. Number 2: Real estate. Taylor Swift is a real estate investor and owns eight properties in the United States. The most expensive is a penthouse in a Tribeca building worth $20 million. She also owns properties in Rhode Island, Los Angeles and Miami. Swift recently put one of her Beverly Hills locations on the market. Price? $84 million. #1 Private jets. Taylor Swift spends most of the year traveling to different states and countries, so it makes sense to invest in a private jet. However, the singer went the extra mile and purchased not one, but two Soul Falcon jets. The jets have 12 seats, enough space to fly part of her entourage. Price: $90 million.