“You look up all the people and say: ‘Ooh, she looks good. He’s not that interesting.’ And just keep going through hundreds and hundreds and hundreds of images, until you find the ones that you love,” Kalman said. “It’s really falling in love with images, wanting to paint them.”

But once the book’s layout hit 300 pages, her publisher cut her off. Kalman said she could absolutely do a whole other book with the photographs she wanted to paint, but didn’t have room for in this edition. At the same time, she didn’t want her illustrations to consume Stein’s paragraph-length sentences and descriptions that are as complex as they are seductively simple. “I want there to be air in it, so that you go through it and you’re not overwhelmed with imagery,” she said. “And the captions from the text are very short phrases, they’re not full sentences most of the time. So there’s a lightness to it, and a kind of flutter of something.”

When Stein wrote The Autobiography of Alice B. Toklas, she purposefully set out to write a bestseller—and she did. Now, with the addition of Maira Kalman’s illustrations, it could be a bestseller again (much in the way that her illustrated edition of William Strunk and E.B. White’s classic writing guidebook, The Elements of Style, became the best-selling edition of that title after it appeared in 2005).