Your Complete Guide to the Most Stylish It-Girls of All Time

Why yes, we are cheating by including these two legends in one pic. But Naomi Campbell and Kate Moss were simply the alpha and omega of ‘90s supermodels, badass Brits, and style icons. Fashion-wise, they were worlds apart—Naomi favored body-conscious, high-glam creations from designers like Azzedine Alaia while Kate favored a quirky mix of thrifted finds with avant-garde designer pieces.

But they were both supernova-hot, impossibly chic, and had an irresistible It-factor that made them the ones everyone wanted to swill champagne and kick it with them. Name a more iconic fashion duo—we’ll wait.

A singer-songwriter who emerged from France’s early-'60s “ye-ye” scene, Francoise Hardy was the sensitive girl with a guitar and a killer sense of style. With her wardrobe of slim-cut trousers, wide leather belts, Chelsea boots, and teeny miniskirts—and, of course, those iconic blunt bangs—she cut a figure of tomboy elegance that set the template for Daisy Lowe, Tennessee Thomas, Alexa Chung and so many It-girls since.

It’s a sad fact of fashion that an outfit that looks au courant right now will look a little tired in one year, and downright laughable in 10. But Chloe Sevigny has the miraculous ability to overcome this curse: Somehow, the looks she wore in 1998 and 2008 look just as amazing in 2018.

Maybe it’s because she never blindly follows the trends du jour, but instead works her own quirky, vintage-inspired style. Unlike many celebs who look “dressed” or “styled,” Sevigny looks like herself, and rarely like anyone else. She's the quintessential New York cool girl.

Rihanna is the embodiment of DGAF. When she wears an underground designer, it can literally put them on the map (hey, Adam Selman, creator of the instant-legend “naked dress”), and when she embraces a trend, she instantly inspires a thousand imitators overnight (hello, every Instagirl wearing teeny shades).

She’s always willing to experiment with outlandish silhouettes, and unapologetically loves and flaunts her body through all its fluctuations. She dresses for herself and no one else—a true inspiration.

A granddaughter of legendary couturier Elsa Schiaparelli, a model who was a fixture in late-'60s Vogue, and a muse to everyone from Halston to Yves Saint Laurent—fashion credentials do not get much more purebred than this, people.

But Marisa Berenson was so much more than just a pretty face: She was a fixture on the socialite scene, a patron of the arts, and a pioneer of the luxe-bohemian style that today finds expression in women from Mary-Kate Olsen to Rachel Zoe.

Anyone who still describes Solange Knowles as sister to a certain superstar is missing the point. Not only has Solo fully emerged as her own unique talent, with plaintive songs that explore love, loss, and Black identity, she’s done it all while pioneering a new kind of otherworldly style.

Ethereal layered gowns, metallic ruffled tops, dramatic jeweled headpieces—Solange effortlessly embraces avant-garde looks and serves up space princess like no other.

Along with Marilyn Monroe, Brigitte is the woman who defined “blonde bombshell.” She also unwittingly created the blueprint for that whole French-girl chic that everyone’s still obsessed with (even if they don’t want to admit it).

Her striped, bateau-neck tees; slim-cut capri pants; ballet flats; cat-eye makeup; and what can only be described as “bedroom hair” single-handedly created the “pouty French beauty” archetype to which many women still aspire.

After years of Hollywood starlets such as Lindsay Lohan and Paris Hilton dominating the gossip pages, Alexa Chung was such a breath of fresh air when she hit the scene around 2007. The gravelly-voiced Brit with a cheeky sense of humor and winsome, '60s-inspired style had plenty of wit to go with her beauty.

After Alexa, every indie girl worth her salt invested in a Peter Pan-collar dress, a pair of ballet flats, and learned to flick her eyeliner—a look Alexa borrowed from Francoise Hardy and brought into the 21st century.

It is impossible to overstate the importance of Diana Ross. She was many things: An iconic singer with the Supremes and solo, an Academy Award-nominated actress, a fashion and beauty icon, and one of the world’s first Black superstars—all feats she achieved in an era of widespread discrimination. And yes, she was also a diva whose style was always about capital-g Glamour, darling: sequins, feathers, gowns down to there, and hair to the sky.

So much recent ink has been spilled about the Duchess of Sussex, it almost seems like overkill. But Markle’s impact on the royal family and the world of style truly matters—she’s the first truly fashion-forward royal. While women like Princess Diana and Kate Middleton were undeniably graceful and always occasion-appropriate, Markle brings a sense of experimentation and youthful sophistication to her tea-length skirts and sheath dresses that sets her apart from any royal before.

This Nicaragua-born model and actress officially entered the realm of style icons when she married Mick Jagger in Saint Tropez in 1971, while wearing an impeccably cut white suit. Throughout the ‘70s, she emerged as the reigning queen of the Studio 54 scene, holding court with luminaries from the art worlds (Andy Warhol, Grace Jones) and bringing an unforgettably dramatic flair to her style—think giant flowers in her hair, red-sequin gowns with matching berets, and, oh yeah, that time she arrived to her birthday party in an off-shoulder dress riding a white horse.

Their fashion sense may be divisive—especially Mary-Kate, who tends to favor more eccentric looks than her twin—but in 2018, no one can deny that these women are fully-fledged style icons, both for their personal fashion and for the work they’ve done helming their luxury label The Row.

In fact, they don’t always get credit for embracing trends years before the rest of us catch on (Birkenstocks, circle sunnies, and Celine-esque oversized layers all spring to mind). But that probably doesn’t bother them—these are women who do their own thing, and let the rest of the world catch up.

From the moment she announced her engagement to Prince Charles in 1981, Diana had an uncanny ability to connect with people and inspire fashion fervor. While some of her ‘80s formal looks veered into ruffly excess (it was kind of the style at the time), she always had a joyful approach to color and silhouette that thoroughly modernized the formerly-stuffy House of Windsor.

By the ‘90s she’d dropped her philandering husband and pared her style down to just the basics: sleek silhouettes, and sexy shorter hemlines that many interpreted as the ultimate revenge.

The fashion publicist entered the world stage fast when she began dating John Kennedy, Jr. in 1994. The pair were constantly followed by paparazzi, and Carolyn’s minimalist, luxe basics—sleeveless turtleneck sweaters, pencil skirts, kitten-heel pumps—was widely imitated by women everywhere, and defined chic in the mid-'90s.

A savvy, New York City blonde in the fashion industry with impeccable style, we see a lot of Carolyn in Carrie Bradshaw, and so many women since who come to the big city to pursue their fashion dreams (and maybe find love, too).