A lavish childhood

Alexandria Caroline, better known as Ally Hilfiger, was born on February 26, 1985, in New York City to legendary fashion force Tommy Hilfiger and his now ex-wife Susie Hilfiger. The American heiress is the eldest of four children. According to Guest of a Guest, she split her time between Greenwich, Connecticut and the Big Apple. She attended Convent of the Sacred Heart, a private, independent Catholic all-girls school costing over US$50,000 a year in tuition fees, per Master of Chemistry.

In Manhattan, she attended the Professional Children’s School, per New York Magazine, a university preparatory school geared toward working and aspiring child actors and dancers.

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Ally, her sisters Kathleen and Elizabeth and brother Richard grew up in a sprawling estate in Greenwich. The historic home spread across eight hectares (20 acres) is an equestrian paradise with a six-stall stable, two paddocks, and a riding arena, per Mansion Global. It also boasts seven bedrooms, nine full bathrooms, a tennis court and a beautiful terraced pool area.

No wonder it is one of Greenwich’s most iconic estate homes. Susie reportedly put the decadent Hilfiger Connecticut estate on sale last year for US$40 million, according to the same source.

A reality TV show stint

Hilfiger was an achiever early on in life. She co-created and starred in the MTV reality series Rich Girls in 2003, which followed the lives of the daughters of two very successful businessmen. Hilfiger and her then-best friend Jaime Gleicher (daughter of Leo Gleicher, founder of Innovation Luggage and head of Gleicher Enterprises) were the stars of the production.

The show delved deep into their luxurious lifestyles. It covered everything from shopping sprees to gossipy lunches in locales such as London, the Hamptons, Hilfiger’s family estates in Nantucket and the tropical British West Indies.

The fashion designer in her surfaced as she spearheaded the women’s clothing line NAHM along with designer Nary Manivong in 2011. The short-lived fashion label closed up shop in less than two years. According to Hilfiger’s Instagram account, she is currently concentrating on her artistic endeavours.

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Dabbling in different trades

For someone who was perpetually ill since the age of seven, Hilfiger did manage a good deal of triumphs. Per Academic, 13-year-old Hilfiger performed on Broadway in Abby’s Song, followed by producing the World War II film Proud at seventeen. She shuttled between attending the Stella Adler Studio of Acting in New York City and simultaneously starting her own vintage accessories business.

Battling Lyme disease

Fourteen years: that’s how long Hilfiger was sick and undiagnosed, per Hello! magazine. She has scribed details of her debilitating disease in her book, Bite Me. A frustrated and always-ill Ally had to resort to drastic action with her father to make him believe in her unending misery.

“I kept telling him I was sick,” she wrote. “He wasn’t getting the message.” Her constant pain, disorientation and discomfort were ruining her life. Her lowest point, per her book, was when she took a silver platter, opened her bowels on it and asked Tommy to get it tested. Then, her father took an 18-year-old Ally to Silver Hill Hospital for psychiatric care.

In an interview with British media, the fashion heiress admitted the illness had transformed her young body into that of a senior citizen: “I couldn’t put lotion on my legs because it felt as if I was being beaten with a baseball bat. I was like an 80-year-old woman. It had taken over every single cell in my body and in my brain.”

Hilfiger wrote her book after shutting down her clothing business. In an interview with Serendipity Social, she said, “I decided to write after I closed my clothing company. I was so frustrated with the constant Lyme relapses, and I thought, ‘I’ve got to do something about this!’ I decided to tell my story because I know a lot of other people out there who are suffering, and maybe I could start to make a little bit of a difference in helping.”

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Finding love

Ally married in true fashion heiress style in a beach wedding ceremony on the Caribbean island of Mustique, in 2017. The daddy-daughter duo teamed up to create a one-of-a-kind boho-inspired gown complete with a cape and intricately adorned veil.

Travelling in style

Ally clearly loves her father’s massive US$45 million superyacht Flag and often shares images of her relaxing on what appears to be her dad’s luxury vessel. The 62-metre beauty features a cinema, a sizeable pool on the sun deck, formal and informal lounge areas, plenty of outdoor space, a well-equipped gym and a wide variety of water toys.