Playboy Magazine, launched in 1953, has wielded significant influence globally since its inception. Described as an American men’s lifestyle and entertainment magazine, it was the pioneering publication to present female nudity and sexuality in a refined format, contributing to the normalization of women taking control of their sexuality. The magazine’s iconic looks, featuring extravagant costumes and lingerie, have left an indelible mark on fashion history.

Marilyn Monroe, 1953

A 27-year-old Hugh Hefner launched the magazine by printing 50,000 copies, which featured Marilyn Monroe on the cover. Monroe is pictured in a low cut, black, satin dress with a white collar. Today we might consider this look classy and elegant, however in the early 50s it was considered revealing and promiscuous. As this look has gone down in history as one of the most iconic magazine covers, it has a rather disturbing history. The pop-culture icon never actually posed for Hefner’s magazine.

Marilyn Monroe on the Playboy cover in 1953.

Monroe never gave consent to use the photo, nor was she paid accordingly for the use of the photo. Hefner plastered the words “The famous Marilyn Monroe Nude” across the cover. Pinup photographer, Tom Kelley, photographed Monroe in the nude in exchange for $50, which she needed for her car payment. She was told the photos would remain faceless and nameless, however that wasn’t the case. Hefner then purchases the rights to these photos for about $500, where they are then featured in the first edition of Playboy. 

Dolly Parton, 1978

In October of 1978, Dolly Parton made her debut as the first country music singer on the cover of Playboy. Parton is pictured wearing the classic Playboy Bunny uniform: bunny ears, a bowtie and collar, and a v-neck body suit. Known for her over-the-top style, and being unapologetically herself, the addition of rhinestones on the bowtie, and pink sequins on the collar and wrist cuffs adheres to Parton’s iconic aesthetic. As well as her famous, big, blonde hair. The issue did not include any nudity, Parton says “I have been asked, back in the day, but that was so totally not me. I would never do that…”

Dolly Parton on the Playboy cover in 1978.

The October issue came out around the same time that Parton’s album, Heartbreaker. Her appearance on Playboy was excellent marketing for her album, Parton says “That was just another way I was trying to market myself, at that time, to kinda get in the mainstream…” In the late 70s, Parton was condemned for her “promiscuity” and her style in general. At this time, it was common for people to stereotype women with blonde hair and big boobs as “bimbos” or “dumb blondes.” When the public saw Parton on the cover of Playboy, they immediately began to enforce those stereotypes. As some people saw this as “bad press,” it was actually one of the smartest marketing moves in Parton’s career. Appearing on the cover not only was good promotion for her brand as a whole, but it was the biggest “f*ck you” to her haters!

Pamela Anderson, 1989

The October 1989 edition of Playboy Magazine was the first of many to include the renowned actress/model, Pamela Anderson. Anderson was the blueprint for young women in the late 80s and early 90s. Women all around the world aspired to be like her, and men aspired to be with her. She is the epitome of the “American heartthrob.” Anderson is pictured wearing a striped blazer with an open button-up, a windswept tie, and a hat covering her lady bits. This issue was the “Bold Back to Campus Issue,” so Anderson’s outfit is mimicking that of a university student…

Pamela Anderson on the Playboy cover in 1989.

As a university student, I can safely say that I’ve never seen one of my colleagues dress in this manner, but this is Hugh Hefner’s world and we’re just living in it! Hefner is infamous for his over-sexualization of everyday topics, so this is no surprise. At the time of this magazine, Anderson had yet to star in hit shows like Baywatch or Home Improvement. Similar to the Dolly Parton issue, people condemned her for her promiscuity on this cover. However, it is the same people condemning her that are now paying her bills!

Naomi Campbell, 1999

The December 1999, holiday issue featured British supermodel Naomi Campbell. Campbell is pictured wearing a two-piece set, a white bondage top with white bikini bottoms. She’s wearing this magnificent white fur coat, as well as what looks to be a ski mask with the face cut out. An interesting accessory choice to say the least. This look was very “out there” for the time it was shot. However, society began to become desensitized to “showing skin” in media because of Hefner’s impact. The cover includes Campbell holding a phone up to her ear, which weirdly foreshadows the infamous “phone throwing” situation.

Naomi Campbell on the Playboy cover in 1999.

In 2006, Campbell reportedly threw her cell phone at her housekeeper, which later resulted in an assault charge. The odd coincidence aside, the December 1999 issue did nothing but boost Campbell’s career. She began her modeling career at age 15. By the time this cover was shot, she had a well-established role in the modeling world. That being said, this experience opened her up to new opportunities furthering her career. Overall, this look takes the cake for the most outrageous.

Paris Hilton, 2005

Last but not least, the one and only Paris Hilton was featured in the March 2005, Sex and Music issue of Playboy Magazine. Hilton is representing the “Sex” portion of the Sex and Music issue with one of the subheadings reading, “Paris Hilton Sex Star of the Year.” Paris is pictured wearing a red satin bodysuit, black fishnets, and red pumps. Something about her expression in the photo, I can just hear her saying her famous line “That’s hot!” This look plays into her sex star persona and personifies the early 2000s. Hilton, being a self-proclaimed sex symbol, has made extreme profits off of her personality and wild party-girl aesthetic.

Paris Hilton on the Playboy cover in 2005.

She is the embodiment of “all press is good press” and has built an empire on that philosophy. Hilton did not pose nude for the magazine, even though that would have aligned with her brand. She kept her audience wanting more, which was a key element to her success. This look definitely goes down in history as one of the most iconic Playboy Magazines to hit the market. That’s hot!