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| Playmate of the Month: Connie Mason, photographed by Pompeo Posar A Style Of Her Own | Haute couture mannequin Connie Mason has a flair and a form for fashion |
| Dear Playboy | |
| Playboy After Hours | |
| The Playboy Advisor | |
 | Playboy Interview: Billy Wilder | A candid conversation with the master of filmic seriocomedy |
| Editorial: The Playboy Philosophy | The seventh part of a statement in which Playboy’s editor-publisher spells out — for friends and critics alike — our guiding principles and editorial credo, by Hugh Hefner | |
 | Novel: Harry, The Rat With Women | No one could look at him without loving him — yet, when he looked out at the world, he wanted still more, and still more…, by Jules Feiffer (part 1) |
 | Fiction: The Queen’s Own Evaders | The trick was to make the best use of those few precious moments between film’s end and anthem’s commencement, by Ray Bradbury, illustrated by Tomi Ungerer |
 | Food: Smørrebrød | Sunny sandwichcraft from the unmelancholy Danes, by Thomas Mario, photographed by Don Bronstein |
 | Fiction: Ugliness, like beauty, is only — Skin Deep, by Brian Rencelaw |
 | Article: Folk, Folkum And The New Citybilly | Casting a critical eye on folk singers — the simon-pure and the phony, the sophisticated and the square, by Nat Hentoff |
 | Humor: Symbolic Sex, by Don Addis |
 | Humor: Playboy’s Party Jokes |
 | Attire: The Rite Time | Middle-aisle garb and guidance for the marry month, by Robert L. Green |
 | Novel: On Her Majesty’s Secret Service | He had been close to death and in deadly peril — then, with the dread brotherhood as his ally, James Bond closed in on his prey, by Ian Fleming (part 3, conclusion) |
 | Pictorial: The Nudest Jayne Mansfield | In her latest flick, Playboy’s perennial favorite romps in the altogether, photographed by Bill Kobrin |
 | Nostalgia: Requiem For The Holidays | Hail and farewell to the wonderful ghosts of those joyous fetes of yore, by Charles Beaumont |
 | Gifts: Playboy’s Gifts For Dads And Grads |
 | Ribald Classic: The Cost Of The Cure | From the tales of Petronius, retold by Paul J. Gillette, illustrated by Leon Bellin |
 | Satire: The Greatest Teevee Jeebies Ever Told | More mad-lib dialog for video’s venerable reruns, by Shel Silverstein |
 | Satire: How To Save Money On Your Wife’s Clothing | More secrets of being successful with women without really trying, by Shepherd Mead, illustrated by Claude Smith |
| Travel: Playboy’s International Datebook, by Patrick Chase |
 Alden Erikson |  Dink Siegel |  Don Madden |  Erich Sokol |
 Gahan Wilson |  John Dempsey |  Eldon Dedini |  Phil Interlandi |
 Erich Sokol |  Unidentified cartoonist |
 Merchandise and book ads |  Merchandise ads |  Playboy Club News |  Record and merchandise ads |
 What Sort of Man Reads Playboy? |
Pipe and PJs 