Drew Barrymore Was A '90s Indie Sleaze Queen - Her Coolest Outfits Of All Time

Now that we're all terminally online, there's a rising nostalgia for the days before late-stage social media when a carefree, party-centered lifestyle dominated the public sphere. And perhaps no one did carefree better than Drew Barrymore, a child actress turned indie ingenue, who was the ultimate '90s It girl. Barrymore laid the groundwork for the rebellious Millennial aesthetic that would follow, somehow managing to give grunge, boho, and girl-next-door all at the same time. She was wild-child-meets-flower-child, as only she could be, and she led the charge on bold hairstyles and grungy, vintage pieces. She was an alt-leading lady before alternative was a genre.

The indie movement — the subculture that emerged in the early-1990s and peaked in popularity around 2008 that Gen Z reinterpreted as indie sleaze  — was effortless, in part because those who embraced it were looking to make a statement that transcended fashion. It prioritized substance and experience over polish and aesthetics. Barrymore was the queen of living offline.

Today, Barrymore is flattered by the profound affect she's had on fashion, as a new generation embraces her signature styles. "They're doing what makes them feel cool and beautiful," she told Elle in 2015. "That's the only important thing." For Barrymore, self-expression has always been the foundation of style—and that's what makes her so unapologetically indie sleaze.

Drew Barrymore wasn't afraid of a high/low mix, as evidenced by the two thrifted slip dresses she wore layered to the 1995 premiere of "Batman Forever." The styling pairs vampy, Gothic details — the choker and dark lipstick — with the super feminine — vintage slips and a flower tucked into her hair. Here, alongside then-boyfriend Eric Erlandson, Barrymore was in her grunge era, embracing the "kinderwh*re" aesthetic beloved by many of the genre's female artists, intentionally challenging the sexualization of female bodies.

On Barrymore, the counterculture style is decidedly "Cool Girl." Her choppy pixie cut keeps the overall ensemble from looking too precious. Instead, the soft, feminine choices look intentional. The edgy details gave Barrymore's image a bit of a grunge look. The effect is fun, in part because Barrymore appears to be less preoccupied with maintaining the perfect details of her look. The rough edges give it an energetic, carefree quality that's pure indie sleaze.

Drew Barrymore attended the 1998 Academy Awards in a black, low-back gown that gave pure '90s minimalism. Still, the free-spirited "Ever After" actress injected plenty of her own personality into the style, adding a little bohemian whimsy in the form of daisies tucked into her blonde bob. Even on a black-tie occasion, Barrymore was playful and she knew how to serve some seriously eclectic vibes.

The sexy — dare we say sleazy? — dress works on the red carpet but it's practically begging to be worn to an after-hours electro party. Plus, the daisies work as pops of personality, transforming a minimal black dress into a '70s revival look that would be right at home in the bright flash of a Cobrasnake photograph.

When pulling from your own closet, often the best indie sleaze is in the details. With the right accessories — a studded belt, long scarf, or even flowers like Barrymore — a simple, foundation piece instantly becomes the perfect throwback look.

What is it about Drew Barrymore's look for the 1999 Saturday Night Live's 25th Anniversary Celebration that makes it such a perfect artifact of indie sleaze? Is it the metallic blue platform shoes? The soft maxi skirt that Phoebe Buffay would have killed for? The loosely tied ribbon belt? Or the shabby chic poncho that looks like a collaboration between someone's grandmother and John Galliano?

No, it's the sweet, casual ponytail that Barrymore chose to finish off the look. The not-quite-polished style is as carefree as it gets, and Barrymore looks energetic. The girlish ponytail is "Cool Girl" effortless. Totally at odds with the red carpet, that ponytail rejects polish. It rejects pomp. It rejects the industry gatekeepers. It's a symbol of unapologetic indie resistance, and Barrymore is its queen.

Sometimes, letting a little more of your true self shine through is the best way to up your indie sleaze factor. Worry less about polish and more about authenticity— forget the arbiters of formality and channel a little of Barrymore's IDGAF.

If you can't choose between accessories, our indie patron saint, Drew Barrymore, instructs us to just wear both. At the 1999 Nickelodeon Kids Choice Awards, Barrymore rejected minimalism with both hands, donning a fuzzy, metallic-flecked scarf, a stack of thin bangles, and a boho-esque headband. Millennials will recall that these flower child-coded headbands were responsible for a lot of headaches but Barrymore looks unfazed.

The whole outfit is a little awkward, from the stiff denim skirt to the 3/4-length sleeves but it's better for it. The ensemble isn't stuffy, and Barrymore's charming, authentic self blazes through. The imperfect details look, not just relatable, but winningly human — a respite from the onslaught of the overly polished, perfected for broadcast, aesthetic. Barrymore offers some maximalist inspo. For a little indie sleaze, don't worry so much about getting the details perfect. Instead, opt for lots of details. Let the personality overflow.

The lime green of Charli XCX's "Brat" album was undoubtedly the people's color of the summer in 2024. But long before she worked it out with Lorde on the remix, Drew Barrymore was making lime green happen.

Always there for a good time, the "Never Been Kissed" star's platform heels hint that she's ready for the after-party. And, clearly not content to predict just one future fashion trend, her metallic handbag presages the 2025 rise of castlecore.

The printed green midi skirt she wore for the 1999 "Women in Film" Crystal Awards—paired with the casual hairstyle and dark, neutral lip that she loves—was personality by order of magnitude. Never one to shy away from a statement piece, "The Wedding Singer" actor looks sexy and vivacious in the bright color. Though she's undergone a stunning transformation through the years, Barrymore is consistent on one thing: Even when she's wearing a suit jacket, she is irrepressibly and unapologetically herself. Takes a page out of Barrymore's book and opt for statement pieces. When in doubt? Go for bold color.