The Top Seducers of All Time

The death of Hugh Hefner in 2017, got us pondering over the meaning and implications of his departure. Is it the end of an era? The end of the golden Playboy era. Perhaps even the end of the archetype of the great seducer? Who these days will dare wander around accompanied by a harem of three girlfriends, each being decades younger than the other?  Was Hugh Hefner the last real Don Juan alive? Certainly not, but it did make us realize that these elegant philanderers are becoming a rarer breed, for better or worse. In view of this alarming tendency, we’ve compiled a list of our favorite seducers for your pleasure and as a tribute to these characters defined by style and incredible social skills. Let us know if you’re seduced or appalled by these primal archetypes that are, we hope, undying.

Giacomo Casanova

The Venetian adventurer made his own name a synonym of seduction. Not only was Casanova the most notorious seducer of the Western world, he was also one of its most vivid storytellers. In his autobiography Histoire de ma Vie ("Story of my Life") he recounts and vindicates his wits and elaborate frauds that allowed him to constantly re-invent himself and become the first self-made gentleman. Casanova’s life defied all categorizations, he obtained a law degree at 17, engaged in a young ecclesiastic career with the Church, became a magician, gabbled with occultism, was imprisoned, escaped, and pioneered the bohemian lifestyle, traveling to all important European cities of the Grand Tour. His innumerable female conquests ranged from aristocrats to nuns.



You seriously thought we were going to only talk about men? How easily fooled you are. Cleopatra was the last Pharaoh, and the first politician to combine as superbly the power of seduction with that of realpolitik. The Egyptian beauty consolidated her power through passionate affairs with the most powerful men of Antiquity, emperor Julius Caesar followed by Mark Antony. She mastered the art of tasteful provocation with impressive rituals, some requiring large quantities of milk to bathe and flirt with Roman generals, others involved dissolving precious pearl earrings into vinegar to shock onlookers. Her elaborate influencing skills have been imitated but are un-paralleled, we irremediably need a president like her.


Serge Gainsbourg

He called himself the ugliest man alive, yet his eloquence made him one of the most sophisticated French seducers. His sharp choice of words and disruptive manners got him the most beautiful women of European Pop Culture from Yéyé singers to French New Wave actors which he all skillfully turned into sex icons. He performed his pygmallion effect with Juliette Greco, France Gall, Anna Karina, Brigitte Bardot whom he momentarily stole from billionaire playboy Gunter Sachs, and the British Jane Birkin with whom he fell in love and bore the talented Charlotte Gainsbourg. He spent his last years with German Vietnamese model Caroline Von Paulus, aka Bamboo. In addition to these carnal and artistic conquests he had two wives and bore 3 other children. Not bad for a man who referred to himself as 'the cabbage head’.


Jack Nicholson

"Physical and sexual vitality is one of the reasons that I'm lively," Nicholson was reported saying. The man has no fewer than six children by five women. Kim Basinger described him as the most highly sexed individual she had ever met, while the late Playboy model Karen Mayo-Chandler revealed that he ate peanut butter and jam sandwiches in bed "to keep his strength up". Oscar winning actress and long time partner, Angelica Huston called him ”Jack the jumper” because of his numerous infidelities, and wrote she was laughed at when suggesting to him marriage. Today, the star of Chinatown, The Shining, and A Few Good Men admits he is lonely and facing death alone because, surprise, women don’t trust him.


Steve McQueen

Perhaps the ‘baddest’ of the Hollywood bad boys, McQueen embodies the barely contained hot temper, the appealing tyrant who must take charge as he would “rather reign in hell than serve in heaven” as John Milton would say. Unlike others who only displayed the qualities of a merciless Don Juan in their early youth to later become deceptively tamed with age (Johnny Depp or George Clooney are your contemporary examples) McQueen was eternally incorrigible in and out of his successful three marriages to Barbara Minty, Ali MacGraw and Neile Adams.


John Casablancas

Often overlooked, the exceedingly handsome John Casablancas managed to become as legally acceptable as a pimp can get by being the only straight male founder of a model agency in 1972. Elite Model Management became Eileen Ford’s main competitor in the so-called “Model Wars”. Many still see him as the initial creator of the supermodel concept as he was the first to manage and represent female talent as celebrities. He indeed applied his ‘packaging’ method to the careers of Cindy Crawford, Naomi Campbell, Carol Alt, Linda Evangelista, Claudia Schiffer, Iman, Heidi Klum and Gisele Bündchen, all of whom thanks to him famously never got out of bed for less than $10,000. Casablancas was however frequently criticized for having sexual relationships with young models. His public affair with Stephanie Seymour in 1983, when he was 41 and she was 15, ended his second marriage to Jeanette Christjansen, a former model and the 1965 Miss Denmark. Enough said.


Jacqueline Onassis Kennedy

Initially, Jacqueline Bouvier was overtaken by her sister Lee Bouvier in the New York socialite’s race to marriage. But Jacky was more ambitious. She patiently waited for the best opportunity to present itself. On an interview she was conducting for the press she charmed a newly elected congressman. The man asked her hand before becoming America’s 35th president. After John F. Kennedy’s assassination in 1963, she reportedly had a passionate fling with brother in law Bobby Kennedy. When moving on to her second marriage she was as picky, if not pickier, and chose someone who could guarantee her, in addition to wealth, uncompromising security. The prevailing arms dealer Aristotle Onassis made the cut. The notorious philanderer left Maria Callas for the first lady widow. Besides marrying the most influential men of her lifetime and seducing unanimously America, she became an arts and fashion icon depicted in Andy Warhol’s pop art, and forging the iconic pink Chanel costume look with its matching pillbox hat.

Hugh Hefner

Hefner epitomizes the modern playboy both symbolically and literally through his legendary magazine that featured everyone who's sexy on this planet starting with Marilyn Monroe. He was one of the most potent advocate of sexual liberation and freedom of expression. The lifestyle he envisioned and made for himself with the numerous sexual partners involved never prevented him from respecting women and being equally respected by them. His controversial declaration “the major civilizing force in the world is not religion, it is sex” is a mantra he proved could be true through his glorious life. The king is dead, long loves the king!

Here are a couple of our True Tribe’s iconic swim shorts to wear when sunbathing by the pool whilst using to your advantage your devastating sex appeal, you handsome charmer.







Leave a comment

All comments are moderated before being published

Shop now