Throughout: 1, 2, 3, 4, 5, 6, and 7: Collection of Betsey Johnson; 8 and 9: photos by George Barkentin, Mademoiselle © Condé Nast; 10: Susan Wood / Getty Images; 11, top left: Bob Laird / AP / Shutterstock, top right: Orato Woodward, Vogue © Condé Nast, bottom: Susan Wood / Getty Images; 12, top: Ben Martin / Getty Images, bottom: Bettmann Archive / Getty Images; 13: Franco Rubartelli / Condé Nast via Getty Images; 14: © Nat Finklestein Estate; 15: Fred W. McDarrah / Getty Images; 16: Ronald Grant Archive / Alamy Stock Photo; 17: photograph by Isi Véléris; 18: Ginny Winn / Michael Ochs Archives / Getty Images; 19, top: Jack Robinson / Condé Nast via Getty Images, bottom: photo by Fairchild Archive / Penske Media / Shutterstock; 20: photo by Fairchild Archive / Penske Media / Shutterstock; 21: Collection of Betsey Johnson; 22 and 23: photos by Fairchild Archive / Penske Media / Shutterstock; 24: Collection of Betsey Johnson; 25: Courtesy © Estate of Barbra Walz; 26: Patricia Nolan; 27: photo by Fairchild Archive / Penske Media / Shutterstock; 28: © Marcia Resnick; 29: photo by Rose Hartman, Collection of Betsey Johnson; 30: Rose Hartman / Getty Images; 31 and 32: Patricia Nolan, Collection of Betsey Johnson; 33: photo by Fairchild Archive / Penske Media / Shutterstock; 34: photo by Ben Buchanan; 35: photo by Fairchild Archive / Penske Media / Shutterstock; 36: photo by Sarah Longacre, Collection of Betsey Johnson; 37: Allan Tannenbaum / Getty Images; 38: Keith Meyers / The New York Times / Redux; 39: Collection of Betsey Johnson; 40: © NY Post / NYP Holdings, Inc.; 41: photo by Fairchild Archive / Penske Media / Shutterstock; 42: Richard Levine / Alamy Stock Photo; 43: Courtesy Steve Madden
Inserts: 44: photo Ulrich Franzen Collection. Courtesy of Frances Loeb Library, Harvard University Graduate School of Design, 45: David McCabe / Condé Nast via Getty Images, 46: Image Courtesy Knoll Archive; 47: David McCabe / Mademoiselle © Condé Nast, 48: The Sunday Times Magazine / News Licensing, 49: Courtesy of Abbeville Press; 50: Courtesy McCall’s Patterns, bottom: Courtesy Barbara Bordnick; 51: Otto Stupakoff / Glamour © Condé Nast, 52: photo by Brian Sanderson, Courtesy of the FIDM Museum at the Fashion Institute of Design & Merchandising, Los Angeles, CA; 53 and 54: Courtesy Hearst Magazines Media, Inc.; 55: Courtesy Hearst Magazines Media, Inc., 56: Javier Gonzalez Porto for Betsey Johnson; 57 and 58: Collection of Betsey Johnson, 59: Michael Ochs Archives / Getty Images, 60: Courtesy Madonna and Steven Meisel; 61: L Gould / IMAGES / Getty Images, 62: Pixelformula / Sipa / Shutterstock; 63: Rose Hartman / WireImage / Getty Images, 64: Shutterstock, 65: Courtesy of Marco Glaviano via Space Gallery St. Barth; 66: Steve Wood / Shutterstock, 67: Sipa / Shutterstock; 68: Shutterstock, 69: photo by Charles Sykes / Shutterstock, 70: photo by Fairchild Archive / Penske Media / Shutterstock, 71: Fairchild Archive / Penske Media / Shutterstock; 72: Sonia Moskowitz-Globe Photos Inc., 73: WENN Rights Ltd / Alamy Stock Photo; 74: photo by Thaddeus Harden, 75: Ngoc Minh Ngo / Taverne Agency; 76: Abdul Ortiz, 77: photo by Justin Coit / Trunk Archive