Hugh Hefner and the Smoking Jacket

Hugh Hefner was a man with his own style. The Playboy founder led a life full of entertainment and entrepreneurship. His red silk smoking jacket was a symbol of his iconic, unique lifestyle.

Hef's silk smoking jacket was a part of his personality. Back in his day, it was acceptable to wear this jacket with a shawl collar while hitting on women. The jacket alone symbolized what it meant to be carefree, in control, and sexy. Hef never lacked confidence, that's for sure. That jacket was in hundreds of different Playboy Mansion photos. He even wore it at media events. When the jacket went to auction, it went for a little more than $40,000 towards charity. People also spent big bucks for more of his silk robes, his beef-carving trolley, a lightbulb that was acutually his from the HOllywood sign, and some of his WWII service medals. This just shows the legendary status of Hefner.

Hefner appeared onscreen being himself in 1967. He smoked a pipe, hung out in his Playboy Mansion library and didn't apologize for his personality. Many wondered if morality had been thrown out the door. Hefner said if American citizens were to truly enjoy life, they needed to liberate their sexuality. He proclaimed this was the mission behind Playboy Enterprises. Don't think Hef was just a man on a mission to talk about sex. He had the business mind to back it up.

In 1953, Hefner walked out on his job as an Esquire copywriter. He raised money for his investors and took out a mortgage loan to launch the future iconic magazine of Playboy. His first issue featured a nude Marilyn Monroe. She didn't give consent to the nude photos. These photos were taken from a 1949 nude calendar shoot. She didn't even shoot them under her stage name. Monroe was not compensated for any of the photos in the magazine, but it sold more than 50,000 copies.

Hefner seemed to always be interested in the sexual side of business. In high school, he wrote an essay stating the US had an issue with avoiding talking about sex. In college, he published an article praising a sexual behavior study by Alfred Kinsey, The Kinsey Report. This report shocked many people because it talked about homosexuality and marital sex. Once Hef published his own magazine with breasts on the cover, the world seemed to flip upside down. This was a new era. Hefner ruffled feathers when he published a science fiction story that Esquire magazine rejected. It told the story of how straight men felt persecuted in this new era where homosexuality seemed more popular. People went crazy writing angry letters to Hefner. Again, he had no apology.

American was watching a butterfly spread its wings. They hadn't seem the urban single man separating himself from the "norm." The "normal" urban single man never talked about homosexuality. This man made it normal for everyone to realize that men could be seduced by nude women and sophistication at the same time. Hef quickly became the man that every man wanted to be. Everyone thought he was enjoying romps with beautiful women every minute. He had a revolving door of women. It wasn't just about the Playboy Mansion. The dream was about those red silky robes, pipes, cocktails, and cashmere sweaters.

Was Hefner just born this way? How does one get so much swagger? He was born in Chicago, Illinois to strict Christian parents. His father was a direct descendant of Plymouth governor William Bradford. His mother begged him to become a missionary. No one in the home was throwing nude photos on the walls or smoking pipes with women wrapped in their arms.

All changed when Hefner's high school girlfriend invited someone else on a hayride. He felt rejected, so he decided to reinvent himself as "Hef." This new guy enjoyed his own jive in the music world and wore loud flannel shirts. Everyone loved this new guy.

Hefner did get married to Mildred Williams in 1949. They had two children as his career took off. Mildren allowed Hef to sleep with other women, so his revolving door of women didn't stop. This marriage only lasted until 1959. He went from being a married man with an open marriage to a swinger. During the 60s and 70s, he admitted to being involved with almost all of his calendar girls. The Playboy Mansion in Holmby Hills, Los Angeles quickly became an iconic place. Hef often chilled out in his silk pajamas working in bed. He entertained many women in that bed, working or not. Hefner claimed he slept with over 1,000 women.

The world seemed to like this new era of openness. The magazine was selling 7 million copies worldwide every month in the early 1970s. Hef went into hosting TV shows and running clubs. The Playboy Bunny worker was born. At the clubs, she wore the famous bunny ears, a corset, a collar, cuffs and a cottontail. If you managed to fly on the Playboy "Big Bunny" jet, you might have been serviced by a Jet Bunny. In the club, you may have met the Cigarette Bunny or Floor Bunny. The success was out of control, in a good way for Hefner.

Hefner claimed he was always in the woman's court. He said he was a feminist before it was a fad. He knew women were the reason for the sexual revolution, and he praised that. He said they could be natural sexual beings just like men. He explained that society tried to make feminism anti-sexual when it was truly the opposite. He funded court cases that challenged the outlawing of birth control. He sponsored cases that down the road led to Roe v Wade. He wanted Playboy to be the cure for puritanism.

Hef's friends said he was shy, yet charming. They said he was always the one that was their for the girl that got in a jam. They said he loved being a celebrity. He often entertained other celebrities at the Playboy Mansion. In the early days, it was normal to see Mick Jagger, Alex Haley and Mort Sahl hanging around at a party.

Hef paved the way for other magazines that wanted to be just like Playboy. Hustler and Penthouse hit the scene. The porn magazines were at war with who could be the best. The magazines tried to show the most skin and the most pubic hair without being censored. Hef stood his ground as a sophisticated man. He didn't try to show more skin or more hair. He stuck with what worked in the past.

The 1980s wasn't the best era for Playboy. The Playboy company lost the London casinos for gambling violations. They had to sell the resorts and record division to another magazine. Chicago's Playboy Building was also sold. Those Jet Bunnies were out the door. Everyone was into go-do dancers instead of bunnies. This meant th corporate jet and the Playboy Clubs were gone.

Hef's sophistication hit a bump in the road when eight of his former lovers stepped forward filing a lawsuit stating he damaged them for practicing palimony. They said he seduced young women, supported them, then discarded them when he no longer needed them. Hefner exclaimed he was the most famous, confirmed bachelor of that time, so there was no way he should be involved in a palimony lawsuit.

Hef decided it was time to throw in the bachelor card, and he got married in 1989 for the second time. This time he wed his Playmate Of The Year, Kimberley Conrad. The mansion became a family home after they welcome two sons. The couple only lasted until 1998 when they separated. Conrad and the boys moved into the house next door. The couple officially divorced in 2010. While they were separated, Hef played his usual games. He enjoyed that revolving door of women once again. He even joined the reality show with "The Girls Next Door." This show in 2005 followed Hef and his three girlfriends as they lived their life at the Playboy Mansion.

The women of the show made names for themselves and moved on with their lives. Hef got a new fiance, Crystal Harris, in 2011. Once she realized he could never truly be a one-woman man, she called off the wedding. Somehow, he won her back. Somehow, he showed her he would only be with her. They finally walked down the aisle in 2012.

Hef's love life was thriving once again, but the magazine wasn't doing so great. By 2015, the circulation dropped to 800,000. In today's world, nude photos in a magazine weren't as exciting. The same nude photos can be found with a click on the internet. Playboy stopped publishing nude photographs for a few years. Hef even passed on creative control of the magazine to his son.

Playboy wasn't going anywhere. Scott Flanders took over as chief executive in 2009. He shrunk the company and made the profits rise. The website grew in popularity. Hefner was still as popular as ever.

Hefner passed away in 2017. His legacy will live on in his children and his magazine. The Playboy Mansion was sold for $100 million. Hugh Hefner changed the way millions of people thought about women. He made nude photographs a world of art. He managed to look sophisticated with multiple women around him in his pajamas. That silky smoking jacket is an article of clothing that represents so much more than a simple jacket. It represents the life and style of a man that changed America.