The Well Dressed Playboy, 1955

...men's fashions had been the raison d'etre of Esquire magazine, but it only emerged as a key component in Playboy once the magazine was firmly established. Sporadic features during the first year of publication had seen Playboy cautiously dip its toe into the waters of men's apparel, but by 1955 it was ready to immerse itself more wholeheartedly in the pleasures of shopping for clothes. That year saw Jack Kessie, a graduate of Drake University in Des Moines, appointed as the magazine's first fashion editor (under the pen-name Blake Rutherford). Kessie had already contributed a few freelance pieces to the magazine, but as appointed to the staff because 'he had the kind of casual elegance which Hefner thought exemplified the Playboy style'.

Kessie's first feature - 'The Well Dressed Playboy: Playboy's Position on the Proper Male Attire' (January 1955) - set the tone for the magazine's early fashion coverage. Resolutely didactic, it counselled readers to be 'conservative in all departments' to avoid being 'caught up in a perplexing, phantasmagoria of color combinations, patterns, styles, designs and cuts'. This sense of conservative elegance was informed, above all, by the smart-but-casual traditions of Ivy League style. 'Few will argue', Kessie asserted, 'against the fact that it is to the Ivy Leaguers that we owe the current national acceptance of the trim, tapered look in men's clothing' (Playboy, October 1955), the fashion editor affirming that there was 'an authentic Ivy look in active sportswear, just as there is in town' and decreeing that readers steer clear of 'the kind of gruesome garbage...touted as the hottest news from Majorca, the Italian Riviera, Cap d'Antibes and Southern California: Old Testament sandals, ballet-dancer shirts that tie north of the navel, too-short swim trunks laced and latticed up the side, etc.' (Playboy, July 1957). Instead, Kessie prescribed a style that would allow men to dress 'casually and correctly...and still retain individuality' - for tennis, white shoes and shorts, worn with a red Lacoste knit shirt; for swimming, 'trim, fly-front cotton poplin trunks with side tabs for a waist-clinching fit'; and for golf, 'pleatless, poplin, olive green shorts' teamed with a 'good-looking glen, plaid, long sleeved shirt' and 'the best golf shoes you can afford' (Playboy, July 1957).

Source:

Playboys in Paradise: Masculinity, Youth and Leisure-Style in Modern America, Bill Osgerby, 2001