Nicky Hilton's Evolution From Childhood To Fashion Mogul

Nicholai Olivia Hilton, a.k.a Nicky Hilton, was born in 1983 in New York City into a very wealthy and famous family. She no doubt had a very charmed life growing up, having lived in the famed Waldorf Astoria hotel with babysitters like Drew Barrymore. Nicky and her older sister, Paris Hilton, were fixtures in the tabloids of the early 2000s, but Nicky was never as much of a partier as her sister and their merry band of socialite friends. The younger Hilton was instead laser focused on her dreams to become a fashion designer, and she began to see those dreams take shape while still a teenager.

Nicky is now married to the heir of a banking dynasty, James Rothschild, and the couple have three young children together. It's easy to imagine Nicky living an easy life of a socialite, but instead she continues to pursue her fashion goals, collaborating with different brands to share her personal style with the masses. Her latest projects include a shoe line, a passion for sustainable fashion, and of course, being a mom. Let's take a look at Nicky Hilton's evolution from childhood to fashion mogul.

Kathy Hilton dressed Nicky and Paris Hilton in matching outfits

Although Nicky Hilton is two years younger than her sister, Paris Hilton, the girls have a history of dressing like twins. Childhood photos show the Hilton sisters wearing matching gowns to family parties and events, ornate, lacy, girly dresses often accessorized with headbands and fancy gloves. "My sister and I were always dressed as twins until we were like 10 or 11, as long as my mom could get away with it. People always thought we were twins," Nicky told Page Six.

And although she claimed in the same interview that she and Paris had outgrown their matching styles, the sisters have often been photographed dressing alike into adulthood. Although not fully twinning, Nicky and Paris wore matching dresses to the 2015 Dennis Brasso fashion show. Nicky's dress was baby blue and Paris wore pale pink. The girls were even rocking similar hair styles, half up with long blond barrel curls.

Notably, the sisters also chose nearly identical wedding gowns for their respective trips down the aisle. While Nicky wore Valentino couture, and Paris wore Oscar de la Renta, the high-necked lace bodices and full skirts were not only strikingly similar to each other, but seemed to be modeled after their own mother, Kathy's, fabulous '80s bridal attire.

She went to an all-girls Catholic school (and longed to make her uniform chic)

Nicky Hilton attended the Convent of the Sacred Heart in New York City, an all-girls Catholic high school. The uniform was a source of frustration for her, as it didn't allow for much self-expression. In her book, "365 Style," Hilton wrote, "I was constantly seeking ways to personalize my look and evolve with the trends while still obeying the school dress code. ... My friends and I yearned to experiment with jewelry, colored tights, and shoes that changed with the seasons." She explained that even nail polish was forbidden and referenced one of her famous classmates who also had to abide by these restrictions. "Crazy to think Lady Gaga attended the same school and obeyed these rules," she mused.

Still, there was one accessory Hilton could get away with without landing in detention — her school bag. "I owned my first messenger-style bag in high school. It was black nylon Prada and I used it as my school bag," Hilton wrote in her book. It seems as though this opportunity to accessorize was an inspiration for Hilton, as she went on to become a handbag designer.

Nicky Hilton started working at 15

Nicky Hilton grew up not just rich, but rich rich. Many kids with her pedigree and bank account might have rested on their laurels and done nothing at all. But Hilton was very determined to work in the fashion industry. In fact, she began working when she was still a young teenager. "I got my first job when I was fifteen years old as an intern at 'Hamptons' magazine, and quickly learned what it meant to work," Hilton wrote in "365 Style."

She credits her parents, especially her father, Rick, with instilling in her a strong work ethic. "So many of the kids we grew up with do not have that work ethic, and I think when everything is handed to someone, it can be really harmful. It's so important to learn the value of earning a dollar and feeling that accomplishment as a result," she told Haute Living.

Of course, as an intern, Hilton wasn't earning any money at her "Hamptons" magazine gig, but that didn't stop her from doing the grunt work of fetching coffees, delivering magazines to advertisers, and even taking out the garbage (per Haute Living). Very humbling for a Hilton!

She went from design school right to the runway

Nicky Hilton graduated high school in 2001 and began taking courses at the Fashion Institute of Technology and the prestigious Parsons School of Design. Hilton didn't take a full course load at either school, and therefore never graduated, but she took what she learned and made her first foray into the world of design.

In her book, "365 Style," Hilton recalled the excitement of traveling to Japan with her sister to model for handbag designer Samantha Thavasa. "I was only seventeen and it was like a dream when the company asked me to design a line of bags for them. Things got even more dream-like when 'Sex and the City' costume designer Rebecca Weinberg was handpicked to style the campaign!" she wrote.

While the handbag collab was an amazing opportunity for Hilton, she took things to the next level when she unveiled her own clothing line in 2004. The line was called Chick by Nicky Hilton, and featured ready-to-wear items such as low-rise jeans and flirty mini dresses. Hilton launched another line in 2006, Nicky Hilton Beverly Hills, which was meant to be a more upscale version of Chick. "I don't want to be one of those celebrities that slaps their name on a label and collects royalty checks," Hilton said. "Everything on that runway reflects me."

Nicky Hilton had a quickie Vegas wedding in 2004

While Nicky Hilton was not as much of a party girl as her older sister, Paris Hilton, she was no stranger to the party scene either. The Hilton sisters ran with a notoriously wild crowd in the early aughts, and the crew found themselves in Las Vegas one weekend in August 2004. Nicky and Paris Hilton were joined by pals Tara Reid, Bijou Phillips, Kimberly Stewart, Lindsay Lohan, and Wilmer Valderrama for a weekend of club-hopping and pool parties.

But the group paused their partying to attend a wedding ceremony, as Nicky married her on-and-off again boyfriend Todd Meister at the Vegas Wedding Chapel. While Harvard graduate Meister and Nicky had reportedly known each other for years, he was 33 years old at the time of their nuptials and Nicky was only 20 (per People).

Still, friends and family thought the two had a decent shot at a future together. Nicky's aunt, Kyle Richards, said, "Todd has known our family for years and we all really love him a lot." Another friend of the couple claimed, "They are both young, attractive, sophisticated. They might have a real chance." Of course, this was a long shot. The marriage was annulled after just three months.

Her hotel venture that almost was

Having created successful handbag and clothing lines, Nicky Hilton decided to branch out and use her design skills for something her family is famous for — the hotel business. In 2006, Hilton announced she would be launching Nicky O, a luxury hotel brand. The first Nicky O hotel was slated to debut in Miami, with a Chicago location to follow soon after. According to a press release, Hilton stated, "Having grown up in the family business I certainly have an understanding of the day-to-day operations at a successful property. With the Nicky O brand I'm looking to combine that knowledge with my entrepreneurial passion in the design world and create an environment that hasn't been seen before."

However, the project never got off the ground. According to The New York Times, the venture fell apart and Hilton even became the subject of a lawsuit. In February 2007, an investment company claimed Hilton was not promoting the project, and that she hired a design company to do the work she was meant to do herself. Later that year, the South Beach hotel Hilton had planned to redesign went bankrupt, foiling plans for the luxury overhaul completely. Luckily, Hilton had other projects in the works, and certainly hadn't been relying on the capital from the failed business endeavor.

Nicholai by Nicky Hilton debuted

In September 2007, Nicky Hilton debuted her new high fashion line, Nicholai by Nicky Hilton, during Mercedez-Benz Fashion Week in New York. Hilton showed off the Nicholai (named for her full first name) Spring/Summer 2008 collection on the runway, whose audience included Russell Simmons, Jenna Jameson, Hilton's parents, and her then-boyfriend David Katzenberg.

The clothes had a sixties vibe, with models rocking short hemlines and high hair. The show also featured bikinis, brightly colored summer dresses, and silky short shorts. The Associated Press said the debut proved that Hilton was a serious designer (via Today).

Hilton showed off Nicholai's fall line in 2008 during L.A. Fashion Week, a collection that included equestrian-inspired looks, schoolgirl skirts, and lots of patent leather. Hilton said (per California Apparel News), "I think [patent leather] makes such a statement. It's so sophisticated and sexy at the same time." It was clear a lot of thought and inspiration went into designing the clothes, and that Hilton was not just a celebrity who'd tacked her name onto an already established brand.

She wrote a book on fashion

In September 2014, Nicky Hilton released her book, "365 Style." In an interview with Celebuzz, Hilton spoke about her book and broke down her 365 method. "The 365 method, I've found, works for any woman with any budget. ... You take the three most common occasions that you dress for ... and then you do, the six stands for the clothing staples, and the five is for the accessories," Hilton explained. When asked how she got the idea for the book, Hilton said, "It really started when the whole social media boom happened ... people started writing me, asking me what to wear."

Hilton had a lot of support from friends and family amid the release of her book. Fans of the "The Real Housewives of Beverly Hills" might remember Hilton's aunt Kyle Richards having an event for the launch of "365 Style" at her Beverly Hills boutique Kyle By Alene Too. Kyle's fellow Housewives, Yolanda Foster, Lisa Vanderpump, and Hilton's other aunt, Kim Richards, were all in attendance, as were Hilton's sister, Paris, and her mother, Kathy.

The heiress married an heir and started a family

In 2011, Nicky Hilton began dating James Rothschild. Rothschild, who was born and raised in the U.K., is a founder and managing partner at global growth tech firm Tru Arrow Partners. But Rothschild is not just wealthy; he comes from one of the richest families in the world. Hilton and Rothschild were engaged in August 2014 and were married in a lavish ceremony at Kensington Palace in London. Of course, her older sister served as Hilton's maid of honor (per Vogue).

The happy couple now lives on a sprawling estate in The Hamptons and have welcomed three children together, daughters Lily-Grace Victoria and Theodora "Teddy" Marilyn, and a son whose name has yet to be revealed. "My husband is very private," Hilton explained to E! News. "This world is very foreign to him." While it would seem that Hilton has her hands full with her brood, she remains open to the idea of having more children in the future. "You know, never say never. But we're very happy right now," she said.

Nicky Hilton has even more fashion collabs

Marriage and motherhood have done little to slow down Nicky Hilton's fashion endeavors. In 2014, she partnered with Canadian brand eLuxe for a 10-piece capsule collection. "I'm a New Yorker who travels to California, so [I was aiming for] a hybrid of California and New York dress for all different occasions. ... All of the pieces go great from day to night," Hilton told Livingly.

Next up was another collaboration, taking Hilton back to her handbag designer roots. She partnered with L.A.-based Linea Pelle for NH Nicky Hilton x Linea Pelle, a handbag line that would debut in fall 2016.

In 2018, Hilton partnered with Tolani for an adorable mommy and me collection called Nicky Hilton x Tolani. "I had seen a bunch of mommy & me lines out there, and I'd found that they were too fancy, so you could only wear them on a special occasion, or they were too expensive," Hilton told New York Family. "So, when I was designing this line, I was really keeping in mind that I wanted to make comfy, fashionable, affordable clothes that you can wear every day." Bonus: She and her daughters could dress alike, à la Nicky, Paris, and Kathy Hilton in the '80s.

Her shoe line and sustainable fashion philosophy

In 2019, Nicky Hilton began what would become an ongoing partnership with shoe brand French Sole. Hilton contributed her very girly, very classic sense of style to the brand. In February 2020, she spoke with The Daily Front Row about her latest collab. "It's very feminine. Lots of cotton-candy-colored pastels, laser cuts, and bows. ... It's what I live in — ballet flats and loafers." She tracks her love of ballet flats back to her mom. "I definitely got the ballet flat bug from my mom. I remember her picking me up from school, always wearing a Chanel ballet flat, in the '90s," she said.

In 2021, Hilton created her very first 100% sustainable collection with the brand. "I try and lead a more sustainable life every day. I consider myself a pretty eco-conscious person — I'm not perfect, but I try and do my part," Hilton told The Daily Front Row. "Even doing small things: like bringing reusable bags to the market, turning lights off when I leave the room, buying sustainable products." It's heartening to have a fashion icon like Hilton speak in favor of sustainability.

Something else Hilton knows a thing or two about is longevity. What could have been a flash in the pan vanity collaboration during her teen years instead blossomed into a legitimate career in the fashion world. Although the Hilton name is famous around the world, Nicky Hilton has absolutely made a name for herself on her own.