Years active: 2000-2010.
Known for: Socialite, blogger, designer, Instagram.
Net worth: $10 million.
Olivia Palermo made her entrance into the socialite life by taking on the queen of social circles at the time, and another It Girl on the list: Tinsley Mortimer. A New York cover story pitted this fresh twenty-year-old against Mortimer, and Olivia – the daughter of a real-estate developer and an interior decorator – went from socialite to model to blogger and designer.
She now boasts 3.8 million followers on Instagram, where she and her model husband Johannes Huebl put up pictures of their yachting, shows, and outfits.
Grace Jones
Years Active: 1970-2000.
Known for: model, singer, actress.
Net worth: $7 million
Grace Jones was the It Girl who broke the mold. Like many on this list, she got her start as a model, and thanks to her unique masculine look, she got people to notice. However, she would then move on to music and release three albums during the seventies.
Her avant-garde concerts garnered her more attention, but she wasn't about to let her star fall. She jumped into acting, and a talent for on-screen performances combined with her big name and striking looks landed her roles next to Arnold Schwarzenegger, Christopher Walken, and Halle Berry.
Tinsley Mortimer
Years active: 2000s.
Known for: Socialite, a descendant of Thomas Jefferson, fashion designer, actress.
Net worth: $35 million.
Tinsley Mortimer's face is a common sight around New York City. She hosted benefits, sat on committees, and even claimed to be descended from the closest thing the United States has to royalty, Thomas Jefferson. A brief scandal struck when rumors about Mortimer's father, who may or may not have been a simple rug salesman. The horror.
Mortimer married an oil heir, got her own reality show, had a bag line from Samantha Thavasa, had a cameo on " Gossip Girl", and was arrested in 2016 for trespassing on the property of sugar scion Alexander “Nico” Fanjul, with whom Mortimer had a rocky relationship.
Nancy Cunard
Years active: 1910-1920.
Known for: Shipping heiress, socialite, writer, political activist, promiscuity.
Net worth: $5 million.
Nancy Cunard loved two things: African-inspired personal design choices, and having intimate relations. To facilitate the second, she had a risky hysterectomy, which nearly killed her but left her unable to get pregnant.
Between spending time with famous artists and writers such as Aldous Huxley, Ezra Pound, Ernest Hemingway, James Joyce, Nancy devoted much of her life to fighting racism and fascism, but suffered from substance abuse. Due to mental illness, her physical health deteriorated, and when she died in Paris she weighed a shocking fifty-seven pounds.
C.Z. Guest
Years active: 1940-1990.
Known for: Actress, socialite, author, fashion designer.
Net worth: $5 million.
There's nothing like royalty, and even though America has no kings or queens, C.Z. Guest is pretty close. Born to an investment banker and C.Z.'s real name is Lucy Douglas, but when her brother gave her the nickname “Sissy” during childhood, the name stuck even though it became C.Z.
She dabbled in acting, married Winston Frederick Churchill Guest, and Ernest Hemingway was the best man. She appeared on the cover of Time in 1962, and had numerous paintings done of her, including by Salvador Dali and Andy Warhol. She was, of course, a friend of Truman Capote. Guest died at the age of eighty-three in 2003.