The 2000s often get a bad rap when it comes to fashion. It was an era of bedazzled everything, low-rise jeans, and questionable layering choices (hello, tank tops over long-sleeve shirts). But as much as some of those trends might make us cringe today, they undeniably shaped the fashion landscape. Fast-forward to now, and we’re witnessing a resurgence of Y2K trends on runways and streetwear, proving that the 2000s left an indelible mark on style. Let’s walk down memory lane and celebrate the top 14 iconic fashion legends of this era who defined and influenced the decade’s bold, experimental, and sometimes chaotic style.
Top 14 Iconic Fashion Legends of the 2000s
1. Britney Spears
No conversation about 2000s fashion is complete without mentioning Britney Spears. Her unforgettable denim-on-denim moment with Justin Timberlake at the 2001 VMAs remains one of the most iconic looks of the decade. From crop tops to low-rise jeans, Britney’s fashion sense epitomized the pop star aesthetic of the time. She also championed trends like velour tracksuits, newsboy caps, and the infamous “visible thong,” which became synonymous with Y2K style. Beyond the stage, Britney’s casual looks, such as flip-flops paired with her signature low-rise jeans, also made waves.
2. Sarah Jessica Parker
Sarah Jessica Parker, as Carrie Bradshaw in Sex and the City, became the embodiment of daring and unconventional fashion in the 2000s. Her wardrobe celebrated high fashion, easily mixing tutu skirts, eccentric hats, and statement accessories. Parker’s portrayal of Carrie introduced audiences to the art of taking risks with clothing, from pairing unexpected textures to embracing bold colors. Her love affair with Manolo Blahnik heels and oversized floral pins defined her character’s unapologetically flamboyant style. Off-screen, Parker’s wardrobe was just as influential, blending sophistication with a touch of whimsy.
3. Avril Lavigne
While many pop stars embraced glamour, Avril Lavigne’s punk-inspired style made her stand out in the early 2000s. She pioneered an edgy aesthetic with loose neckties, baggy cargo pants, and sweatbands, embodying rebellion through her wardrobe. Her signature pin-straight hair, chunky highlights, and smudged eyeliner set a beauty standard for alternative teens. Avril’s look was more than just fashion—it was a statement of individuality that resonated deeply with her fans. By defining a subculture, she proved that personal style could also be an act of defiance.
4. Nicole Richie
Nicole Richie’s journey from reality TV star to style icon began with her time on The Simple Life. Alongside Paris Hilton, she made Juicy Couture tracksuits and Von Dutch trucker hats a cultural phenomenon. Richie’s fondness for oversized sunglasses, Balenciaga bags, and glossy lips became staples of 2000s fashion. As she transitioned to a more refined, bohemian-inspired aesthetic, Nicole solidified her position as a fashion influencer. Her ability to balance casual trends with high-end pieces showcased her versatility and understanding of style.
5. Christina Aguilera
Christina Aguilera was a fearless fashion risk-taker, redefining what it meant to push boundaries in the 2000s. From the controversial leather chaps in her “Dirrty” era to her constantly evolving hair colors, Xtina’s style was unapologetically bold. Her dramatic makeup, including rhinestone face gems and exaggerated eyeliner, became a hallmark of her look. Christina’s ability to embrace extreme transformations inspired fans to explore their unique expressions of beauty and fashion. Her impact extended beyond music, influencing both high fashion and streetwear trends.
6. Lindsay Lohan
In her prime, Lindsay Lohan was the quintessential “It Girl” of the 2000s, blending Hollywood glam with relatable teen style. Her roles in Mean Girls and Freaky Friday brought babydoll dresses, denim miniskirts, and oversized belts into mainstream fashion. Beyond her on-screen appearances, Lindsay’s signature spray tan and glossy lips set beauty trends that dominated the decade. Her mix of approachable casual wear and red-carpet glamour made her an aspirational figure for many. Lindsay’s style, though often understated, was undeniably influential during the Y2K era.
7. Christina Milian
Christina Milian exuded confidence through her sultry and daring fashion choices on the red carpet and in her music videos. Her go-to pieces—low-rise jeans, exposed thong straps, and cropped tanks—embodied the sexy yet edgy vibe of the early 2000s. Leather miniskirts and daring accessories further emphasized her bold approach to style. Christina’s unapologetic embrace of body-conscious clothing paved the way for contemporary R&B stars who emulate her aesthetic today. Her wardrobe was a blend of attitude and allure, making her one of the standout style icons of the decade.
8. Paris Hilton
Paris Hilton was, without a doubt, the ultimate 00s fashion icon. Known for her “party princess” aesthetic, she dominated the decade with Juicy Couture tracksuits, Von Dutch trucker hats, and rhinestone-encrusted accessories. Paris’s love for metallic Louis Vuitton bags and ultra-mini skirts made her a paparazzi favorite, constantly cementing her status as a trendsetter. Her fearless embrace of glitzy, over-the-top fashion embodied the indulgent and carefree spirit of the era.
She turned her style into a brand, influencing millions to embrace Y2K trends confidently. Even today, Y2K fashion owes much of its resurgence to Paris, proving her influence on style is timeless. Whether stepping onto a red carpet or strutting down the street, Paris always ensured all eyes were on her.
9. Lauren Conrad
Lauren Conrad’s laid-back California girl aesthetic offered a refreshing contrast to the flashier styles of the 2000s. On The Hills, she showcased a wardrobe of babydoll dresses, tube tops, and denim capris, often paired with oversized sunglasses and her signature beachy waves. Her bohemian-inspired outfits, with neutral tones and flowy fabrics, appealed to those who preferred understated elegance. Lauren became a relatable style icon, showing that chic fashion didn’t have to be loud or over-the-top. Her wardrobe balanced casual charm and sophistication, making her approachable yet aspirational. Conrad’s timeless approach to dressing influenced fans and continues to inspire those who love effortless, classic looks. Whether attending an event or running errands, Lauren always exemplified “California cool.”
10. Jennifer Lopez
Jennifer Lopez delivered one of the most unforgettable fashion moments of the 2000s with her green Versace dress at the Grammy Awards. Beyond that, J.Lo became synonymous with blending glamour and urban edge in her wardrobe choices, turning heads with every outfit. Her style was as versatile as her career, from fur-trimmed coats and velour tracksuits to figure-hugging gowns. She consistently pushed the boundaries of fashion, redefining what it meant to be sexy and classy.
Jennifer’s ability to evolve her look while staying true to her Bronx roots made her stand out in fashion. Her innovative approach to blending high-end and streetwear-inspired countless trends that endure today. Whether on stage or on the red carpet, Jennifer Lopez always exuded star power and undeniable style.
11. Beyoncé
As Beyoncé transitioned from Destiny’s Child days to a solo superstar, her fashion choices evolved into a celebration of luxury and bold aesthetics. She often gravitated toward golds, metallics, and statement accessories, which became her signature look during this transformative time. Beyoncé’s red carpet appearances showcased glamorous gowns, daring prints, and impeccable tailoring that accentuated her curves and highlighted her confidence.
Her ability to blend elegance with boldness set the standard for pop star fashion, making her a muse for designers and fans alike. Beyoncé’s wardrobe during the 2000s reflected her rise as a global icon, with each outfit amplifying her power and charisma. Beyond the glitz, she used her style to convey her individuality and artistic vision. Even today, her fashion legacy from the 2000s inspires many.
12. Victoria Beckham
Victoria Beckham, known to many as Posh Spice, seamlessly transitioned from pop icon to high-fashion mogul in the 2000s. Her sleek, minimalist outfits, tailored pieces, and love for monochromatic ensembles hinted at the designer she would later become. Oversized sunglasses, sharp silhouettes, and neutral tones became her trademarks, exuding sophistication with every appearance. Victoria cultivated an aura of mystery and refinement, positioning herself as more than just a celebrity but a true style icon.
Victoria’s meticulously curated fashion choices, balancing simplicity with bold impact, made her a trendsetter of the decade. Her transformation into a respected designer cemented her place in the industry, where she continues to inspire. Her 2000s style was a blueprint for modern minimalism and high-fashion elegance.
13. The Mean Girls Girls
The 2004 hit movie Mean Girls became a treasure trove of 2000s fashion inspiration. The film captured the spirit of the decade’s trends, from the Plastics’ iconic pink ensembles to Regina George’s infamous cut-out tank top. Karen’s velour tracksuits, Gretchen’s mini skirts, and their glossy lip glosses were quintessential Y2K staples embraced by fans worldwide. Beyond its humor, Mean Girls showcased how fashion could define social dynamics, especially in high school.
Lines like “On Wednesdays, we wear pink” immortalized the movie’s sartorial impact on pop culture. The characters’ blend of preppy and glamorous trends made them instant style icons of their time. Even today, Mean Girls continues influencing fashion and serving as a nostalgic nod to the 2000s style.
14. Jennifer Aniston
Jennifer Aniston’s style in the 2000s epitomized chic simplicity and timeless elegance. On and off the red carpet, she gravitated toward clean lines, sleek silhouettes, and neutral tones that never went out of fashion. Her affinity for classic black dresses and minimalist accessories proved that less could indeed be more in creating a lasting impression. Beyond her clothing, her layered, face-framing haircuts—especially “The Rachel”—became a beauty phenomenon that defined a generation.
Jennifer’s effortless approach to style struck a chord with fans who admired her for being relatable yet undeniably glamorous. She perfectly balanced contemporary trends with enduring staples, making her a consistent favorite among fashion enthusiasts. Whether attending an event or enjoying casual outings, Jennifer always exuded a polished and approachable vibe.
Celebrate the Timeless Influence of 2000s Fashion Icons
The fashion icons of the 2000s weren’t just following trends—they were creating them. Their bold choices, from Juicy Couture sweatsuits to punk-inspired cargo pants, defined an era of experimentation and self-expression. Today, as we see the resurgence of Y2K fashion, it’s clear that their influence continues to inspire new generations. Whether rocking a velour tracksuit or a pair of low-rise jeans, remember that fashion, like history, is cyclical. Who was your favorite 2000s fashion icon? Did you ever try to replicate any of these looks?
