Playboy January 1955

Playboy February 1955

Covergirl
Leigh Lewin and Arlene Kieta (not nude)

Features
A Change of Air by Ivan Gold
Kley's Winter Art by Heinrich Kley
The Most Horrible Story by John W. Jakes
How To Make Money By Shepherd Mead

This issue does not exist

Features
This issue does not exist! It was never published!
Playboy was not able to meet the publishing deadline for the March issue.

Playboy April 1955

Playboy's Playmate of the Month
Marilyn Weltz photographed by Hal Adams

Covergirl
Unknown (not nude)

Features
The Hunger by Charles Beaumont
A Tithe for Charity by P.G. Wodehouse
Pictorial of Naked Advertising
Modern Art as a Hobby by Roger Price

Playboy May 1955

Playboy's Playmate of the Month
Marguerite Empey photographed by Hal Adams

Covergirl
The Playboy Bunny (not nude)

Features
"The Eighty Year Run" by Irwin Shaw
"TV's Ad Glibber" by Keith Hefner
"How to Be a Fair-haired Boy" by Shepherd Mead
"Naked Lady" by Mindret Lord

Playboy June 1955

Playboy's Playmate of the Month
Eve Meyer photographed by Russ Meyer

Covergirl
Eve Meyer (Nude inside and also appears as the centerfold) photographed by Russ Meyer

Features
"All-Time All-Star Jazz Band" by Jack Tracy featuring Louis Armstrong, Roy Eldridge & More!
"Successful Love" by Delmore Schwartz
"From Searle's Sketchbook" sketches by Ronald Searle
Illustrators Show (Pictorial)

Playboy July 1955

Playboy August 1955

Covergirl
Joanne Arnold (not nude)

Playboy September 1955

Playboy October 1955

Playboy's Playmate of the Month
Jean Moorehead photographed by Hal Adams

Features
"The Taming of the Rake" by Anson Mount
"The King" by James Jones
"Stags for Fun and Profit" by Jay Smith
"The Advenstures of Hector" by Thorne Smith

Playboy November 1955

Playboy December 1955