Cover: Coat, $2,195, and pants, $575, Calvin Klein Collection; calvinklein.com/collection.
p. 22: From left: Bec Parsons; Ike Edeani.
p. 24: Robbie Fimmano.
p. 26: Clockwise from top: Uwe Ommer 1984 The Bahamas © The Pirelli Calendar; Kamil Bialous, Thomas Goldblum; Karen Collins; Christaan Felber.
p. 30: Kevin Tachman/Trunk Archive.
p. 38: KayWaal and A. Ferzan for Superette.
p. 42: Coat $2,395, and suit, $1,795, Bally; 844-442-2559. Sweater, $750, Calvin Klein Collection; Calvin Klein Collection, 645 Madison Ave., NYC, or calvinklein.com/collection. Shoes, $865, Marc Jacobs; marcjacobs.com.
p. 44: Jacket, $3,500, shirt, $600, and tie, $210, Dior Homme; Dior Homme stores. pp. 46-47: 2006, Wenn; 2003, Reuters/Gary Hershorn/Corbis; 1998, Walter Iooss Jr./Sports Illustrated/Getty Images; 1995, Warner Bros/PhotoFest; 1993, Patrick Murphy-Racey/Sports Illustrated/Getty Images; 1990, Ken Levine/Getty Images; 1988, courtesy of Nike; 1985, Steve…