Legendary Outfits From The 'Indie Sleaze' Era We're Still Thinking About Years Later

Of all the fashion trends to have come and gone in the last 20 years, indie sleaze is probably one of the most fun. Unlike other trends that require looking at least somewhat put together, indie sleaze is the complete opposite, favoring styles that look like you just threw on whatever was lying around your room. The trend is a mishmash of grunge and punk rock styles, with room for personalizing or elevating different looks. And if your cat-eye makeup from the night before isn't smudged into raccoon eyes, then you're missing out on just how fabulously easy the indie sleaze style can be.

"The overarching theme was rock 'n' roll energy," photographer Mark Hunter, who was at the helm of documenting the era, told Vogue in 2022, adding that showing up to a party, or anywhere for that matter, looking only half put together (as opposed to fully snatched) was the point. "There was a functionality to the fashion," explained Hunter. "If someone spilled a drink on your outfit, it wasn't terrible. It would just kind of blend in." Which is great news for anyone who can't wear white for more than five minutes without getting a stain.

It's because of this easy-breezy and je ne sais quoi approach to fashion that we've witnessed the reemergence of the indie sleaze aesthetic on several occasions, and we're sure there will be even more revivals of the style in years to come. While there are certainly standout outfits from this unique fashion era, which existed between the early 2000s and about 2010, there are some legendary looks — like almost everything Chloë Sevigny wore — that will live in our memory forever.

These days, Drew Barrymore is aging like fine wine after cutting out alcohol and embracing a more mature personal style. But in the early 2000s, the actor was the epitome of indie sleaze. At the June 2003 premiere of "Charlie's Angels: Full Throttle," Barrymore was photographed, alongside castmate Cameron Diaz, wearing black leather pants and a shirt that read, "My boyfriend is out of town," while holding up a bottle of Dom Pérignon. "For whatever reason, I was like, I don't want to wear a dress, I just want to put on my T-shirt," Barrymore explained to People in 2024. With her disheveled hair and black eye makeup, Barrymore's look was iconic. 

When it comes to iconic indie sleaze styles, Chloë Sevigny is definitely on the list. In 2002, Sevigny was photographed at an event, looking chic but a bit messy, wearing a black shirt, black blazer, and cut-off gray denim shorts. She completed her outfit with slicked-back hair, large dangly earrings, and vibrant red lipstick, which is always a good idea. "In the indie sleaze era, people weren't so concerned with things being so crisp," Sevigny told Elle in June 2026. "It was a little softer, and I love that and miss that about that time."

One of the important things about indie sleaze is that you need to go big or go home. In other words, your partner had better be on-trend too, which is exactly what Kate Moss got when she dated The Libertines' lead singer Pete Doherty. In 2005, the two attended Glastonbury Festival together, and this photo was taken, proving just how committed Moss was to the trend in her shimmery minidress and mud-covered rain boots. Considering Moss' style these days, she's not only a celebrity whose makeup never really left the '90s, but she hasn't totally given up indie sleaze either.

Although Taylor Momsen got her start as an actor, by 2009, her band, The Pretty Reckless, signed a record deal, and her style got a major overhaul. Fully in rock-star mode, Momsen appeared at the MTV Europe Music Awards in November 2010 wearing a black minidress, leather jacket, and exposed red garters. This look wasn't just an attempt to gain more punk rock cred; the indie sleaze style movement as a whole was a sign of the times, as music journalist Matthew Perpetua told Thrillest in 2022. "To me, this sleaze era is definitely the Bush era, and I think there is a significant vibe shift that happens within 2008 that leads into something else."

Similar to Taylor Momsen, Sky Ferreira, who was also very much a part of the indie sleaze trend, got there just in time. Like Momsen, Ferreira signed her first record deal in 2009, but also continued to dabble in other projects like acting and modeling. In April 2011, Ferreira attended the premiere of "L'amour Fou" at the Tribeca Film Festival , wearing a miniskirt, oversized band tee, red zip-up jacket, and black boots. In this grunge 2.0 look, Ferreira was fully indie sleaze.

While some of the celebrities mentioned here adopted this punk-adjacent style somewhere in the middle or towards the end of the trend, Amy Winehouse came onto the scene right at the cusp of the indie sleaze fashion movement. She became a sort of patron saint of the style, because we knew she wasn't just following trends — she was setting them. As much as Winehouse was known for her incredible singing voice, she was also a fashion icon for her unique look, always appearing stylishly disheveled and aloof. In July 2010, Winehouse was spotted leaving the Runway Club in her usual indie sleaze garb: a tank top, cut-off shorts, and ballet flats.

When it comes to celebrity kids who inherited their parents' famous style, as the daughter of Lisa Bonet and Lenny Kravitz, no one does it quite like Zoë Kravitz. Because of this, Zoë was expertly rocking indie sleaze in her late teens and early 20s. When attending the premiere of "Breaking Upwards" at the IFC Center in April 2010, she delivered nothing less than fashion-icon-in-the-making energy with her black knee-high socks, black oxford flats, a black blazer and matching skirt, with a band tee, and a black, wide-brimmed hat. 

Despite launching luxury brand, The Row, in 2005, the personal style of Mary Kate Olsen and Ashley Olsen has always leaned more indie sleaze than stealth wealth, especially during the height of the trend. In October 2006, the twins were photographed at the Paris Fashion Week's Christian Dior show looking epically grungy in their fur pieces (which may or may not be real), black clothing, and disheveled hair that looks like it needs to be washed. Ashley completed her look with a red crocheted beret and chunky jewelry.

When you dig around indie sleaze history, there's a name that comes up a lot: Alexa Chung, a model and "It" girl of the era. What's interesting about Chung's take on the trend is that she leaned more preppy and less messy, as seen here in a miniskirt, tee, black jacket, black boots, and a Chanel bag. "It's accurate to describe it as indie," Chung told W in 2024 about the trend. "I don't know about the sleaze, but definitely indie, because it was a collection of people who came together around a particular music scene."