Cindy Crawford Told Us the Stories Behind Her Most Iconic Photos

Cindy Crawford—the original model-turned-mogul, whose career longevity and brilliant business sensibilities are nothing short of awe-inspiring—is doing something she never thought she’d do: publishing a book, Becoming, to coincide with her upcoming 50th birthday. But this isn’t the typical glossy, fancy coffee-table book that you’d expect from an iconic beauty who’s shot with everyone from Herb Ritts to Steven Meisel and has hundreds of covers under her belt. “I’ve done a lot of incredible pictures, but I don’t see my career that way,” Crawford says. While the book does include a slew of phenomenal handpicked photos documenting Crawford’s illustrious career, she’s also written a series of essays telling the story of how she went from a small-town girl to the world’s biggest supermodel to a powerhouse businesswoman. (In addition to numerous other successful ventures over the years, Crawford is currently at the helm of two major brands, Cindy Crawford Home and the skincare line Meaningful Beauty, which sold a reported $100 million in products in 2014.) Expanding her portfolio far beyond that which made her first famous, Crawford helped pave the way for future celebrity entrepreneurs like Gwyneth Paltrow, Reese Witherspoon, and Blake Lively.

In an exclusive interview with Byrdie, Crawford looks back on some of her most iconic photos, sharing never-before-heard stories behind the beauty and fashion looks for each image.