Everyone wants to be an It Girl, but only a few defined entire eras. From Paris Hilton turning fame into a business model to Zoë Kravitz industrializing cool, these women didn’t just wear the clothes—they shifted culture. This isn’t about trends. It’s about power, visibility, and the outfits that launched a thousand moodboards. Let’s break down the It Girl eras that still shape the way we dress, post, and exist online.
1. Paris Hilton (2003–2007): The Y2K Fame Machine
Between 2003 and 2007, Paris Hilton engineered a new type of celebrity—one built entirely on image. Long before social media made personal branding a requirement, Paris monetized visibility through reality TV, paparazzi culture, and a hyper-stylized public persona that turned every outing into content.
Embed from Getty ImagesHer signature look—rhinestones, Juicy tracksuits, Von Dutch trucker hats, tiny purses, and even tinier dogs—wasn’t just aesthetic, it was strategy. Every outfit contributed to a visual brand so consistent it became its own language. She wasn’t dressing for events—she was dressing to dominate headlines.
Embed from Getty ImagesParis’s real innovation was turning lifestyle into business. She sold music, perfume, books, and appearances not through skill alone, but through persona. She blurred the line between authenticity and performance—and proved that in the right media climate, fame could be the product.
Embed from Getty ImagesHer legacy isn’t just aesthetic—it’s systemic. Today’s influencers operate on the same logic Paris pioneered: visibility as value, branding as identity. Y2K fashion may resurface in cycles, but the fame economy she helped engineer hasn’t gone out of style.
2. Alexa Chung (2008–2012): Tumblr Girl Reign
From 2008 to 2012, Alexa Chung defined an era of fashion that valued personality over polish. She emerged at the exact moment Tumblr, fashion blogs, and It Girl culture were converging, offering a look that felt distinctly individual: mismatched, offbeat, and cool without explanation.
Embed from Getty ImagesHer style was built on contradiction. She’d pair Peter Pan collars with beat-up denim, ballet flats with blazers, or delicate blouses with leather. Her influence wasn’t in trendsetting—it was in normalizing personal style as a legitimate fashion stance. She made disheveled look deliberate.
Embed from Getty ImagesAlexa’s reach extended past her wardrobe. As a TV presenter, British Vogue contributor, and eventual designer, she brought her aesthetic into mainstream fashion from multiple angles. The Mulberry “Alexa” bag confirmed her retail clout, and her book It became a style reference for a generation.
Embed from Getty ImagesCulturally, Alexa helped shift fashion away from perfection and toward personality. Her It Girl status wasn’t about dressing up—it was about dressing like yourself. That sensibility still defines how style influence operates today, especially online.
3. Chloë Sevigny (1995–1999): The Downtown Anti-Heroine
Between 1995 and 1999, Chloë Sevigny defined a version of It Girl that was the opposite of polished. She became a style reference not by following trends, but by rejecting them. Her fashion impact was rooted in instinct: vintage layering, unconventional pairings, and a refusal to present as styled—even when she was.
Embed from Getty ImagesHer looks pulled from thrift stores, not showrooms. She wore baby-doll dresses with combat boots, grandpa sweaters with mini skirts, and Mary Janes with white socks before that was a curated Pinterest board. Her approach wasn’t nostalgic—it was practical, reactive, and fully her own.
Embed from Getty ImagesAt a time when Hollywood was driven by sleek silhouettes and designer labels, Chloë showed up in outfits that felt lived-in, sometimes disjointed, but always deliberate. She helped usher in early normcore and downtown anti-fashion—long before those aesthetics had names or marketing behind them.
Embed from Getty ImagesHer legacy hasn’t faded. Today’s TikTok alt-girl aesthetic mirrors her exact formula, even when it doesn’t name-check her. What sets her apart is longevity: she didn’t pivot to trend cycles—she stayed rooted in personal style. Two decades later, she’s still relevant not because she chased cool, but because she set the terms for what cool could be.
4. Sienna Miller (2004–2006): Boho Girl Canon
Between 2004 and 2006, Sienna Miller turned boho chic from fringe trend to fashion standard. Her style—cowboy boots, tiered skirts, crochet camisoles, oversized belts—defined the early-2000s shift toward undone, vintage-inspired dressing. The look wasn’t new, but she made it aspirational, wearable, and instantly replicable.
Embed from Getty ImagesHer version of boho was unpolished but intentional. Outfits looked thrown together in the best way: floaty silhouettes, slouchy accessories, tousled hair. It didn’t read as styled by committee—it looked like instinct. Even when she pivoted into mod styling during her Factory Girl phase, the core remained: unfussy, grounded, and slightly chaotic.
Embed from Getty ImagesSienna’s influence hit fast. High-street brands mass-produced knockoffs. Scarves, vests, peasant blouses—every detail of her wardrobe showed up in stores within months. She set the tone for what would become “festival fashion,” years before it was marketed as such.
Embed from Getty ImagesHer cultural imprint is clear: she didn’t just spark a trend—she built a look that became a retail category. Boho chic wasn’t just about aesthetics anymore; it became a lifestyle shorthand. Sienna gave the 2000s their most digestible fashion formula, and brands are still recycling it two decades later.
5. (1989–1994): The Grunge-Goth Blueprint
From 1989 to 1994, Winona Ryder introduced a new kind of It Girl—one that rejected Hollywood polish in favor of thrifted tailoring, dark palettes, and deliberate disinterest. Her film career (Heathers, Reality Bites, Edward Scissorhands) shaped Gen X cinema, but her personal style shaped the visual language of 1990s alt-cool.
Embed from Getty ImagesHer aesthetic pulled from both grunge and goth: combat boots, oversized blazers, slip dresses, minimal makeup, and vintage jewelry that felt personal, not styled. While others chased glamour, Winona wore boyish suiting to red carpets and made secondhand look subversive. Her looks didn’t ask for attention—they held it anyway.
Embed from Getty ImagesShe presented fashion as resistance. The layering, the muted tones, the intentionally unstyled hair—it wasn’t about being offbeat; it was about opting out. That refusal to engage with trend-driven fashion made her an anchor for anyone looking beyond the mainstream.
Embed from Getty ImagesWinona’s impact didn’t fade. Her 90s outfits are reposted daily. TikTok’s obsession with dark academia, quiet goth, and thrifted minimalism can all be traced back to her. She didn’t brand herself—she embodied something, and that authenticity is why her style still resonates.
6. Zoë Kravitz (2015–2020): The Cool Girl Standard
Between 2015 and 2020, Zoë Kravitz locked in the blueprint for modern cool. Her style walked a line between intentional minimalism and inherited grunge, turning secondhand staples and high fashion into a single, coherent aesthetic. She didn’t invent the “cool girl” look—but she industrialized it.
Embed from Getty ImagesEarly on, she leaned into boho-grunge: fringe, floppy hats, vintage tees, and layered jewelry straight from the ‘70s playbook. But once she hit her stride with Big Little Lies and high-profile film roles, the styling got sharper—Saint Laurent gowns, sheer dresses, and sleek tailoring.
Embed from Getty ImagesThe signature? Understated clothes with maximum presence. She wore slip dresses like streetwear and leather jackets like armor. Every look felt low-effort on the surface but was clearly calibrated—right down to the pixie cut and minimalist jewelry. It wasn’t about styling trends. It was about owning them before they peaked.
Embed from Getty ImagesHer influence was quieter than her peers, but no less powerful. Zoë’s version of It Girl status didn’t rely on virality—it relied on consistency. She proved that muted, moody, and minimalist could be just as trend-setting as maximalist glam.
7. Bella Hadid (2016–2022): The Viral Stylist
Bella Hadid’s It Girl power was rooted in execution. From 2016 to 2022, she became the unofficial stylist of the internet—reviving Y2K and ’90s fashion through a lens of precise layering, archival sourcing, and viral-ready looks.
Embed from Getty ImagesShe wasn’t just nostalgic. She was strategic. Bella mixed claw clips, cargo pants, and thrifted tanks with runway-level tailoring and vintage Gaultier. Every outfit felt deliberate, even when it looked thrown together. That balance made her paparazzi photos more influential than editorials.
Embed from Getty ImagesThe Coperni spray dress may have been her headline moment, but the real impact came from the daily street style: shoulder bags, oversized outerwear, track pants with tiny tees. She made casual look directional. TikTok followed. Depop followed. The resale economy followed.
Embed from Getty ImagesBella didn’t just update the supermodel template—she made it interactive. Her looks weren’t just documented; they were replicated, dissected, and sold. She turned off-duty dressing into a full-time influence economy.
8. Rihanna (2010s–Now): The Reigning Institution
Rihanna’s It Girl era never ended because she never treated it like one. Starting in the early 2010s, she shifted from pop star to fashion authority, using both red carpets and streetwear to redefine what mainstream style could look like. The 2014 CFDA Fashion Icon Award wasn’t a peak—it was a checkpoint.
Embed from Getty ImagesHer style framework was built on contrast: do-rags with couture, jerseys with stilettos, sheer crystal gowns one night, oversized denim and fur the next. She erased the line between casual and formal, using unpredictability as strategy. No outfit felt styled for trends—they felt styled for her.
Embed from Getty ImagesAs her image solidified, so did her empire. Fenty Beauty set new standards for shade inclusivity, while Savage X Fenty reimagined lingerie marketing through diversity and spectacle. Even her maternity fashion—low-rise jeans, crop tops, sheer fabrics—challenged the narrative that pregnancy should be styled conservatively or hidden.
Embed from Getty ImagesCulturally, she moved past being an It Girl and into being a fashion institution. Designers watch what she wears. Trends move around her orbit. She didn’t adapt to the industry—she forced it to catch up. Her influence isn’t seasonal; it’s structural.
9. Lindsay Lohan (2004–2007): The Tabloid-Era Icon
Between 2004 and 2007, Lindsay Lohan embodied a turning point in celebrity culture—when fame stopped being controlled and started being consumed. After Mean Girls, she was both a bankable actress and a tabloid fixture, caught in the overlap between rising star and public spectacle.
Embed from Getty ImagesHer It Girl image lived in extremes. She was filming studio movies by day and photographed outside clubs by night. She wasn’t just attending the party scene—she was headlining it, often alongside Paris Hilton and Nicole Richie. That omnipresence, whether intentional or not, defined her entire era.
Embed from Getty ImagesVisually, she defined early-2000s “messy glam”: low-rise jeans, Uggs, layered tanks, fur-lined jackets, and giant sunglasses. Her iced coffee runs became their own category of street style. She also helped push boho-glam into the mainstream, fusing festival-inspired pieces—scarves, beaded tunics, denim minis—with a Hollywood edge.
Embed from Getty ImagesLohan’s cultural relevance went beyond clothes. Her media saturation foreshadowed today’s influencer visibility and raised conversations around celebrity exploitation and mental health. She represented a turning point—when It Girl status became less about mystique and more about constant access, for better or worse.
10. Mary-Kate & Ashley Olsen (2004–2008): The Messy-Luxe Chic
From 2004 to 2008, Mary-Kate and Ashley Olsen helped define the boho-chic It Girl. No longer just child stars, they became fashion fixtures on NYC streets—dressed in billowy shawls, floppy hats, flared jeans, and maxi dresses.
Embed from Getty ImagesMary-Kate leaned maximalist: caftans over jeans, giant belts, and layered necklaces that felt more vintage flea market than designer showroom. Ashley’s take was slightly more refined—peasant blouses with tailored jackets and slouchy denim. Their accessories—floppy hats, massive hobo bags, and scarves year-round—cemented the aesthetic.
Embed from Getty ImagesWhat set them apart was how unfiltered the styling felt. The Olsen look wasn’t curated to be flattering or trend-conscious—it was personal, layered, and unpredictable. Yet it was copied everywhere, especially by college-aged women and fashion blogs trying to bottle that same messy-luxe energy.
Embed from Getty ImagesTheir influence extended beyond trendsetting. In 2006, they launched The Row, marking their transition into serious fashion design. But their boho era remains culturally significant—it showed that fashion clout didn’t have to be minimal, or camera-ready. It could be chaotic, oversized, and still completely iconic.
Bonus: Hailey Bieber (2020–Now) – The Clean-Girl Algorithm
Since 2020, Hailey Bieber has turned the clean-girl aesthetic into a mainstream style economy. She didn’t originate the slick bun, neutral palette, or glazed skin—but she scaled it, branded it, and turned it into a visual language adopted across platforms.
Embed from Getty ImagesHer influence is algorithmic. Every look is filtered through a minimalist lens: oversized outerwear, dewy skin, no overly loud prints. Street style becomes moodboard material, and even a crew sock becomes a reference point. The Rhode rollout followed the same formula—controlled, aesthetic-first, and fully in sync with the image she curated.
Embed from Getty ImagesWhat defines Hailey’s It Girl era is consistency. No reinventions, no chaos cycles. The styling stays in a tight loop: structured basics, soft glam, low-saturation everything. It’s not spontaneity—it’s brand maintenance. She doesn’t just wear the clean-girl look—she built the playbook for monetizing it.
Embed from Getty ImagesIn a post-maximalist moment, Hailey offers a version of It Girl culture that’s heavily mediated, quiet, and market-ready. She’s not the wild card or the trend gambler. She’s the system reset: aspirational, calm, and fully optimized for the feed.
The TL;DR That Matters
It Girl status has never been about just looking good—it’s about shaping the culture in real time. From chaotic paparazzi nights to perfectly curated street style, each of these eras left a mark that still shows up in what we wear, how we post, and who we idolize. Some set trends. Others built entire ecosystems. Either way, the legacy isn’t just fashion—it’s cultural architecture.