Friday, June 19, 2026

Steve Jobs Gave Famous Novelist Sister Fashion Advice, Designer Clothes

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Much will be coming out from Walter Isaacson‘s authorized biography of Apple founder Steve Jobs today. His full sister was novelist Mona Simpson, whose debut novel, “Anywhere But Here,” chronicled her own strange childhood with their mother. Later, after meeting Jobs in 1986, Simpson based another novel, called “A Regular Guy,” on her newfound brother. Isaacson writes in the new biography that Jobs, who was thrilled to meet Simpson, disapproved of the way she dressed. He didn’t like her to dress like “a struggling novelist.”

One day a box arrived from the designer Issey Miyake.  Isaacson writes: “He’d gone shopping for me,” Simpson said, “and he’d picked out great things, exactly my size, in flattering colors.” There was one pantsuit that he had particularly liked, and the shipment included three of them, all identical. Jobs told Isaacson: “I still remember those first suits I sent Mona. They were linen pants and tops in a pale grayish green that looked beautiful with her reddish hair.”

Jobs had also wanted to improve the looks of his much older girlfriend, famed singer Joan Baez. He once showed her a red dress at a Ralph Lauren  Polo store, Baez tells Isaacson, and told her she should buy it. He didn’t pick it up himself for her, however. He did gift her with an early Apple Macintosh word processor.

PS According to Isaacson, Simpson and Jobs were full siblings, children of Joanne Simpson and Syrian born Abdulfattah “John” Jandali, who abandoned them. Steve was famous put up for adoption. In the end, Isaacson writes, Jobs became close to both his biological sister and mother. As for the father, they never met officially. But Jandali told Mona Simpson that Jobs had once eaten in a restaurant he’d managed, they’d met (not knowing their relationship), and that Jobs had been “a big tipper.”

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Roger Friedman
Roger Friedman
Roger Friedman is the founder and editor-in-chief of Showbiz411. He wrote the FOX411 column on FoxNews.com from 1999 to 2009, where he covered Michael Jackson, and previously wrote the "Intelligencer" column at New York magazine in the mid-1990s, where he covered the O.J. Simpson trial. He also edited Fame magazine. His bylines have appeared in The New York Times, The Washington Post, the New York Daily News, the New York Post, Vogue, Details, and the Miami Herald. He is a voting member of the Critics Choice Awards (Film and Television branches), and his movie reviews are tracked by Rotten Tomatoes. With D.A. Pennebaker and Chris Hegedus, he co-produced the 2002 documentary "Only the Strong Survive," which screened at Directors' Fortnight at the Cannes Film Festival.

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