At the down of the new Millennium Olivia Inge debuted at le Bal in Christian Dior haute couture in 1999 when she was 18. The descendant of Prime Minister William Gladstone was already a fashion model and later became one of Britain’s top models. She’s worked for premium designers such as Vivienne Westwood (her model debut at the age of 16), Tom Ford, Givenchy, YSL, Alexander McQueen, Alberta Ferretti, and Helmut Lang.  Aside from her modeling career, Olivia is a successful entrepreneur – she and her sister Alexia own “Cult Beauty”, an online “insider’s guide to the world’s best beauty buys” (totally worth following).

The niece of President George Bush also chose Christian Dior haute couture for her social debut at le Bal in 2000. Lauren Bush was then 16 years old but made an appearance to remember for years. She was already an Elite model for three years and shortly after le Bal she appeared on the covers of “Tatler”, “Town and country”, ”W Magazine”, Pirelli calendar and “Glamour”. She’s worked for Dooney & Bourke, Tommy Hilfiger and Gai Mattiolo. In 2006 she graduates from Princeton University with a degree in anthropology. This summer she’ll be celebrating her 30th birthday and the 10th anniversary since she met her husband David Lauren (Ralph Lauren’s son). The couple married in 2011 in the RL Colorado ranch where, naturally Lauren was wearing a dress by Ralph Lauren. Lauren Lauren (what a beautiful name it turned) is the CEO, Creative Director, and Co-Founder of FEED Projects, a joint world food program with the UN and one of world’s sexiest vegetarians.

Barbara Berlusconi astounded society in Chanel haute couture back in 2001 when she was 17. Daughter of the former Italian Prime Minister Silvio Berlusconi (one of the richest men in the world) lady B, as the Italian press nicknamed her, is a businesswoman and the chief executive of soccer club AC Milan. Work doesn’t interfere with motherhood for the beautiful and ambitious heiress. She has two sons – Alessandro and Edoardo – from her 10-year relationship with JP Morgan associate Giorgio Valaguzza, whom she separated in 2011.

Same year, same-age debutante Amanda Hearst chose Carolina Herrera for her le Bal gorgeous look.  The heiress to the Hearst media conglomerate and former fashion model is now an activist against puppy mills, special projects editor of Town and Country magazine and an associate market editor at Marie Claire.  As a model she has appeared on the covers of Town & Country, International Harper’s Bazaar, Cosmopolitan, and other major magazines, and has been featured in Vanity Fair. Still single and extremely attractive, Amanda is one of the top hottest billionaire heiresses making their own name.

2002 is the year when great politic descendant met grand fashion heiress. 22-year old Xénia Virganskaya Gorbacheva and 19-year old Margherita Maccapani Missoni were among the best dressed debs of that night 12 years ago, respectively in Christian Dior and Emanuel Ungaro haute couture. Besides the famous origin, the two young women have gorgeous weddings and modeling careers in common.

Gorbacheva was modeling for Laura Biagiotti just before she got married in 2003 for her cavalier at le Bal Kirill Solod and continued her Public Relations education at Moscow’s University of International Relations. She became a journalist and worked for “Grazia” magazine.  Xénia is now the general director of “National Musical Corporation” and a mother of soon-to-be 5 year-old Alexandra from her second marriage to Dmitry Pyrchenkov, ex-manager of the singer Avraam Russo.

Missoni was the brand ambassador for her grandparents’ fashion house and an IMG model working for the same label. She got married in 2012 for Eugenio Amos – a race cars driver and they have a son – Otto who will celebrate his first birthday this year. Margherita is currently pursuing an acting career at Lee Strasberg Theater and Film Institute, NYC and has a fashion blog.

16-year old Dree Hemingway debuted in Christian Dior haute couture in 2003. She is the great-granddaughter of legendary author Ernest Hemingway and her mother is an actress. Dree has already an extremely successful modeling career with Elite Model Management. She’s worked for iconic brands such as Givenchy (her debut as a runway model in 2009, in Paris), Calvin Klein, Gianfranco Ferré, Salvatore Ferragamo, Karl Lagerfeld, Chanel, Gucci, Jean Paul Gaultier, Valentino, H&M, and Paco Rabanne to name a few. She has also done editorials for Harper’s Bazaar, and multiple national editions of Vogue.  Dree is now turning to acting as a career.

11 years after Harumi Klossowski de Rola entered society at le Bal, another descendant of the famous painter Balthus made her debut in 2004. This time it was his granddaughter and daughter of his son – writer Thaddeus Klossowski de Rola, born in 1944 from Balthus’s first marriage to Antoinette de Watteville – a Swiss aristocrat whom he divorced in 1967(they were separated 20 years before that) to marry Setsuko (Harumi’s mother). Anna Klossowski de Rola was an 18-year old beauty, dressed in her mother’s glamorous creation – Loulou De La Falaise.  Loulou had started her own line just the previous year after working as a jewelry designer and a creative assistant for Yves Saint Lauren for more than 30 years.  With a background like that, it’s no wonder that Anna is now a contemporary art curator and a creative artist with an immense sense of style and beauty.

Following her sister’s footprints, Anastasia Virganskaya Gorbacheva made her society debut at the same time, two years after Xenia, at the age of 17, dressed in Versace haute couture. She’s also a journalist, graduated from the same university her sister did and worked also for “Grazia” magazine. She is now editor-in-chief of a Russian lifestyle website and married to successful fashion PR specialist Dmitry Zangiev since 2010.

2005 was an extraordinary deb season for the Renouard Bal. One of world’s hottest billionaire kids – Sofia Barclay, Molly Flattery – granddaughter of screen legend Steve McQueen, Ashley Bush – 5 year-younger sister of 2000 deb Lauren Bush and Rainsford Qualley – daughter of actress Andy MacDowell, stole the glam of the night.

Sofia was only 16 but wore her Elie Saab haute couture as if she does it naturally on an everyday basis. Now, at 25 as a heiress of the Telegraph Media Group, she’s looking at $1.6 billion heritage and dreams of a career in acting.

The black and white Christian Dior haute couture only just attributed 18-year old Molly’s natural beauty with her blonde locks and blue eyes. Her mother died in 1998 and she lived with her father and grandmother, actress Niele McQueen. Molly is now an actress, quietly following her family’s heritage.

16-year old Ashley Bush wore Ralph Lauren (an only natural choice, keeping in mind her sister’s husband) at her le Bal debut. It’s been 9 years since then and she’s been actress and producer, now filming documentaries and web series “Route By Route” – she travels around the globe with classmate Raffi Sapire to discover what drives successful women entrepreneurs. Ashley also frequently contributes to Newsweek’s Women in the World Foundation as a freelance writer.

Dazzling in a black Gaultier Paris haute couture, then 16-year old Rainey Qualley – Andy MacDowell’s middle child – also made a debut to remember. She is now and actress, a singer and a songwriter, who became Miss Golden Globe 2012. Attractive, young and talented, the 23-year old beauty surely has a great career ahead of her.