Five of the World's Most Fashionable Music Videos

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Style and sound combine to create unforgettable moments in pop culture's rich history, as these iconic videos by the likes of Madonna, Grace Jones and TLC demonstrate

Fashion and music have long made comfortable bedfellows. The equation is quite simple: musicians benefit from having a strong look on stage, while designers can increase their cultural cachet by linking themselves with whoever has the coolest sound at the moment. That might sound shallow, but consider the implications of this – music and fashion can fuse together in the format of the music video. While fashion and trends can be ephemeral, changing on a whim and with the seasons, and while even chart-toppers can become one-hit wonders, a well made music video is a vehicle for cultural synthesis. There’s no better format for crystallising a mood, an atmosphere, a way of living. When artists and directors come together, often with crucial input from a favoured designer or a stylist, the result can be a powerful antidote to all that ephemera: something timeless that is still quintessentially of its moment, all at once – a fact well known by Apple Music, as it launches its new fashion channel. Here, we chart five of the most stylish music videos ever to have graced our screens.

1. Madonna: Vogue (1990)
“Beauty’s where you find it,” Madonna reminds us in Vogue, her 1990 hit single. The video, shot in chic black and white by David Fincher, helped to bring vogueing from Harlem’s ballroom culture to a much wider audience. Featuring a host of trained dancers against an Art Deco backdrop, Madonna’s video for Vogue represented a seminal turning point in pop culture and style. We see Madonna and her dancers move enigmatically to the music in loose, oversized tailored suits. Several shots recall specific fashion photographs by Horst P. Horst, as in the shots of Madonna posing in an intricate satin corset and in a turban. That famous cone bra corset, as designed by Jean Paul Gaultier and already iconic from its features in the video for Express Yourself, makes an appearance, too, cementing Madonna’s grip on the style of the time.

2. Grace Jones: Pull Up to the Bumper (1982)
The video for Grace Jones’s Pull Up to the Bumper was something of an early breakthrough for the music video, which was still in the process of defining itself in the early 1980s. What Jones herself wears is barely visible – a well cut suit, a sharp hairstyle, all usual trappings of her stage wardrobe – but that does not take from this video’s style status. It’s a postmodern work of art, in its imposition of Jones’s floating image over time-lapse scenes of traffic and city lights at night from ‘The Grid’ section of Godfrey Reggio’s Koyaanisqatsi, released that same year. Jones then appears like an elegant ghost, fading in and out of images of factory production lines and highways alike, and the relentless pace of modern life becomes inescapable underneath the beat.

3. Hole: Celebrity Skin (1998)
By the time Hole’s Celebrity Skin was released in 1998, Courtney Love and her band were successfully shaking off their Kinderwhore image from the early 1990s and trading it in for something a little more traditionally glamorous. Richard Avedon had photographed Love for a Versace campaign that year, and the video for the lead single echoes that shift. The band play in more streamlined black velvet and leather, while Love’s blonde waves glitter with tiny diamonds. Consider this a reflection of the changing attitudes towards beauty over the course of the 1990s. The glamour of Celebrity Skin may be tongue-in-cheek – see the beautiful dancers in garish purple dresses (nods to Marilyn Monroe in Gentlemen Prefer Blondes) suspended like puppets on strings – but it’s still glamour, more concretely defined than the rough and ready babydoll dresses Love was known for. Her reincarnation as a modern Hollywood fixture was now well underway.

4. TLC: No Scrubs (1999)
Director Hype Williams was responsible for creating a certain kind of late 1990s music video that many will recognise immediately – expensive, radiant and glossy, often through a fisheye lens and with many markers of excess. Flashing lights, chrome interiors and other futuristic elements optional. In doing so, the prolific Williams helped escort rap and R&B further into the mainstream, and the video for No Scrubs was a classic of this genre. T-Boz, Chili and Left Eye dressed in coordinated, black cyberpunk costumes like a trio of revenge-seeking heroes from an S&M-inspired sci-fi. These costumes, designed by long-time TLC collaborator stylist Julieanne Mijares, were intended to mimic the new, computer-generated sounds found on their album Fanmail. Those looks are interspersed with simple, white outfits featuring feathers and low-slung trousers. In one interview, Mijares said the white looks were inspired by Issey Miyake’s fabrics, recreated with leather and silks, and they share an element of that perennial 1990s style – something so of its time that it can somehow persist, remaining iconic for years to come. 

5. Grimes: Genesis (2012)
“To be completely honest, I think I prefer making videos to making music,” Claire Boucher told Pitchfork on the release of Genesis, an entrancing video shot in LA in 2012. Genesis firmly established Grimes as a woman in charge of her creative output, an auteur who does things purely on her own terms. Featuring a pink-braided Brooke Candy, a cruising Escalade and an albino python, the film pays homage to many popular music videos of the past 20 years, but avoids simply retreading old ground. Riffing on video game aesthetics as much as music videos, the fashion nods to Japanese anime and Harajuku subculture as well as contemporary micro-trends originating in online communities like Tumblr at the time. Boucher cites the work of Hieronymus Bosch as a major inspiration for the video, but it’s the hyperreal collaging of maximal references – everything from Britney’s I’m a Slave 4 U performance at the 2001 MTV VMAs, to the work of Jean Paul Gaultier, to late 1980s NYC club kid style – that makes the video for Genesis one that will stand the test of time as an icon of its era.

This article was created in collaboration with Apple Music.