Nicole Richie's Stunning Style Transformation

Few faces were as emblematic of the 2000s as Nicole Richie. The socialite shot to reality television stardom as Paris Hilton's best friend and partner-in-crime on "The Simple Life," and she quickly became a fixture of tabloids and gossip blogs. Richie's look, from her enormous, bug-eyed sunglasses to her platinum blonde hair, defined the decade and launched a thousand trends. She worked closely with one of the era's most famous celebrity stylists, Rachel Zoe, and she was a poster girl for the boho-chic "Zoebot" look before pivoting to a fashion career, designing vintage-inspired jewelry that would be become a staple in many A-list closets.

Today, the once-ubiquitous Richie, daughter of singer Lionel Richie, has opted to retreat somewhat from public life. As she's transitioned to a more quiet lifestyle in the fashion industry, the star has abandoned the on-trend approach that defined her early years, opting for a more mature and classic personal style that feels and timeless. Once the queen of a raunchy Y2K aesthetic, Richie had since rebranded herself as fashion heavy hitter, known for her impeccably tailored looks that maintain a unique tension between sleek modernism and bohemian maximalism.

Nicole Richie embodied the early-2000s rock and roll aesthetic on the red carpet for a pre-Emmy party in 2003. From the high contrast streaks of darkness in her blonde hair to the guitar pick earrings to the Louis Vuitton pochette bag, this look is absolutely giving millennium reality star chic. Taken shortly before "The Simple Life" premiered in December 2003, Richie was just becoming a household name as one of the decade's most recognizable It Girls. Like other socialites from her cohort, Richie favored styles that brimmed with femininity and sex appeal, toughened up with masculine details like her black boots here.

At the time, rock music was enjoying a major revival, and the influence was filtering through to broader pop culture. Richie's earrings most foreshadow her marriage to Good Charlotte front man Joel Madden, who she would begin dating in 2006 and marry in 2010. For an iconic L.A. girlie, a little pop-rock grunge was irresistible.

Nicole Richie had a whimsical pink moment at a 2004 party to celebrate the second season of "The Simple Life." Alongside then-BFF and costar Paris Hilton, she rocked a bohemian spin on a hot pink princess dress. By then, the fake tan, heavy black eyeliner, and blonde hair had become a signature look for the reality star.

At the time, Richie was known for bold — and sometimes outright tacky — choices. But in an interview with Refinery29, she revealed that, though her style has evolved, she stands by all those short skirts and Von Dutch trucker hats: "At that time, I was really feeling Britney and Christina, and that was who I was. However you wanna do it right then, that's how you have to do it — not worry about in 10 years if you're gonna look back and be totally embarrassed, because you're always gonna be embarrassed." There's a playfulness to Richie's outfits during these years, as she leaned hard into the trends that would come to define the decade. It's that willingness to follow her impulses, to good and bad effect, that made her an icon.

By the mid-2000s, Nicole Richie's style evolved dramatically as she began working with celebrity stylist Rachel Zoe. In 2006, she appeared at the launch of the PlayStation 3 wearing a patterned Missoni mini dress on the red carpet. Under Rachel Zoe's tutelage, Richie refined her image and made fewer appearances on the "Worst Dressed" list. She traded her bold hair extensions and revealing dresses for a more sophisticated and demure look. She rapidly became one of Rachel Zoe's most high profile clients and a disciple of the stylist's L.A.-meets-70s-glam brand. From the subtle smoky eye to the vintage dress print, this is peak "Zoebot."

But the working relationship was short lived. Though Rachel Zoe's flair would linger on in Richie's revamped aesthetic, Richie fired the stylist in 2006. After a high-profile struggle with her weight, Richie "wanted to surround herself with positive people and influence" and that did not include Rachel Zoe, an insider source told Us Weekly (via the Los Angeles Times).

In 2008, the former reality star pivoted more fully into fashion. She launched her own jewelry line, called House of Harlow 1960. The designs offered a pop of Richie's signature luxe-boho style to her fans, with designs that blended vintage 60s and 70s influences and emphasized natural materials like leather and semi-precious stones. Her pieces were popular with other A-listers of the moment, including Kim Kardashian and Lindsay Lohan. In the following years, House of Harlow 1960 — named for her lookalike daughter Harlow — would expand to offer clothing and accessories, and Richie would shorten the name to simply House of Harlow.

After a friendship-ending feud with Paris Hilton and the end of "The Simple Life," Richie underwent a stunning transformation, rebranding herself as a different kind of celebrity — one to be taken more seriously by fashion elites. Richie's style, both in her personal looks and in her choices for House of Harlow, continued to foreground vintage glamour. "I'm really inspired by the '60s and '70s. I love ... Keith Richards' rock-star style and, of course, Jackie O," she told Glamour during a 2008 photoshoot.

At the 82nd Academy Awards in 2010, Nicole Richie stunned in a floor-length beaded gown by Reem Acra. In an interview with Refinery29, Richie confessed that she made the choice to go dramatic as then-fiancée Joel Madden's date. "I don't go to the Academy Awards every year. I'm not a movie actress and that was the only time that I had ever been," she said. "The reason was that I actually was Joel's date that night ... and was excited to be on his arm."

Of the dress, she remembered loving it immediately. "I'm a big fan of long sleeves, so I think that that was part of it. That gown has a very '70s feel about it, too. And, the way that it kind of shines in the light with all of those very cool muted jewel tones ... it was just something that I found very beautiful and breathtaking," she explained. The dress, with its glittery caftan vibe, perfectly captures what had become Richie's new signature, which blended old Hollywood luxury with a bohemian California twist and lots of sparkles.