An Ode To Fiona Apple’s Music Video Style

At a time when some of us are feeling lonelier than usual, Fiona Apple’s capacious vulnerability feels especially needed and relatable right now. And thankfully she just released Fetch the Bolt Cutters, her first album after eight years, giving us a reason to revisit her archive.

At the 1997 MTV Video Music Awards, Apple infamously accepted the award for Best New Artist by calling out celebrity culture. She started her speech by saying, “I’m not going to do this like everybody else does it,” which is a phrase that could also apply to every aspect of her creative output. “What I want to say is, everybody that’s watching, this world is bullshit. You shouldn’t model your life about what you think that we think is cool and what we’re wearing and saying,” she said. “Go with yourself.”

Apple’s an unyielding singer-songwriter, and if her headline-making speeches don’t convey that she marches to the beat of her own drum, then the string of music videos that she’s released over the course of her career undeniably do. For the most part, the wardrobe Apple wears in her music videos are masterclasses in understated 1990s minimalism, whether it be the iconic (and ultimately controversial) visual she released for “Criminal,” or “Fast As You Can,” one of her multiple collaborations with her then-boyfriend director Paul Thomas Anderson. Some are more extravagant affairs, like “O Sailor,” wherein Apple steers a ship in a sequined gown and roams the galleys in a caramel-colored silk slip. No matter what style mode she was working in, Apple goes with herself, always. Below, in chronological order, we’ve compiled some of Apple’s best music video style moments.

“Sleep to Dream” (1997)

The video for “Sleep to Dream,” the first song off Apple’s debut album Tidal, won her the MTV Video Music Award (back then, the award was called “Best New Artist in a Video”). In the Stéphane Sednaoui-directed video, Apple struggles to fall asleep as she sits with her back up against a leopard-printed ottoman in a wood-lined room, dressed in a pair of plum-colored pants, and a very ’90s high-neck tank top with criss-cross straps holding it together. Later on, she’s pictured in a similarly shaped top, although this one’s an appropriately dreamy blue velvet. Watching it now, it’s a late ’90s time capsule that gives some early indication of Apple’s idiosyncratic style.

“The First Taste” (1997)

The fourth single from Tidal, “The First Taste” is breezier than most contemporary Apple tracks. The video starts off with Apple in a sleek black slip dress and a sheer red blouse that rustles in the wind. It then cuts to Fiona wearing the same black dress and a pair of heels as she lies down on a royal blue carpet with huge speakers by her side. Apple’s then wearing it at a house party, and it’s the only real party outfit Apple wears over the course of her music videos (usually, as in “Sleep to Dream,” she’s alone).

“Criminal” (1997)

If you’ve only seen one Fiona Apple video, it’s likely his one. Director Mark Romanek has described it as a tribute to Nan Goldin’s seminal photographs of her 1980s social scene, but to critics of the video at the time of its release in 1997, it was the epitome of heroin chic. Apple’s style, when she’s wearing more than just silk lingerie, is yet again a snapshot of the late-’90s: there’s a midriff-baring, subtly sequin-covered blue three-quarter-sleeve shirt and a brown crochet skirt, both of which look like they’d be choice thrift store finds today.

“Across the Universe” (1998)

Apple covered the Beatles’ “Across the Universe” for the 1998 Gary Ross film Pleasantville, which tells the story of two siblings (Reese Witherspoon and Toby Maguire) who get trapped in a 1950s television show. The black-and-white video, directed by Paul Thomas Anderson (the first in a slew of videos he directed for her), runs with this theme. Apple is fully at peace dressed in a pair of over-ear headphones and a strappy black tank top and blissfully oblivious to the kids in argyle sweaters with slicked back hair that destroy the diner around her.

“Fast as You Can” (1999)

Another PTA joint, “Fast As You Can,” from her sophomore album When the Pawn…, is one of Apple’s best music video style moments, and one of the simplest: she waits for the subway (in what appears to be a European city) in a perfectly fitting black tube top, which she affixed straps onto with safety pins, and a low-slung, long black skirt. It’s an indelible late ’90s silhouette, and one that Apple pulls off particularly well.

“Limp” (2000)

The video for “Limp” (again, directed by Paul Thomas Anderson) finds Apple in more surreal territory. Apple wakes up in the middle of the night, puts on red lipstick, and picks out a well-tailored periwinkle suit-dress from her walk-in closet. It’s one of Apple’s most formal looks yet, and it proves she’s got more range than those former midriff-baring tops and baggy pants might imply.

“Paper Bag” (2000)

The final Paul Thomas Anderson-directed video from When the Pawn…, “Paper Bag” makes the case that Apple could have been a convincing screen siren a century ago. Sitting in a bar in a grand Art Deco building, she wears a classic red gown that looks like it’s from the 1930s. Background dancers in bowler hats cartwheel behind her, and she joins in on the choreography towards the end of the video.

“O’ Sailor” (2005)

“O’ Sailor” provides us with Apple’s most extravagant fashion moment yet: Apple roams the halls of a cruise ship in a peach-colored silk gown as theatrically outfitted “sailors” dance around her. In the crux of the video, she finds herself caught in the middle of a chandelier in a sequined gown and a pair of striped red socks.

“Not About Love” (2005)

“Not About Love,” another single from her album Extraordinary Machine, finds Apple back in clothes that look more true to her actual closet. In the Michael Blieden clip, Zach Galifianikis’s and Apple’s fictional relationship seems to be on the rocks. Galifianikis lip syncs the song’s lyrics for the duration of the video, even as Apple rolls her eyes at him. As Galifianikis runs down the street, Apple follows close behind in a simple beige, cropped turtleneck and some high-waisted slacks. The top looks like she cut it up herself.

“Every Single Night” (2012)

The video for “Every Single Night” the lead single from Apple’s 2012 album Idler Wheel…, is one of the most surreal in her archive. In the video, Apple is face-down in the dirt in a soft blue slip dress as snails crawl all over her body, then she’s walking down by the Eiffel Tower in a light yellow satin trenchcoat. At other times, she’s got an octopus on her head, and then she’s a marionette in a Batsheva-esque black gown in a pool of alligators. Even in video that plays out like a bad dream, Apple still has some standout fashion moments.

Originally Appeared on Vogue