1. Vogue – Madonna (1990)

Madonna owes a big debt of gratitude to the LGBT community for her 1990 hit ‘Vogue’. The song and video were the embodiment of the dreamy, alluring promises of fashion and were inspired by the gay underground community in Harlem, New York that in the late 70s gave birth to a new form of dancing known as ‘voguing’. The dance could be described as a combination of fierce model poses, ballet, contemporary dance and Egyptian dance. It’s wild and precise at the same time. ‘Vogue’ solidified Madonna’s edgy persona and helped to ignite gay culture’s influence on the mainstream, making it an obvious winner on this list (read all about Madonna’s iconic fashion moments here). Check out Strike a Pose, a documentary about the lives of the dancers in ‘Vogue’, 25 years after it was a hit, which will show at the Hong Kong Lesbian Gay Film Festival, starting on September 17.

2. Niggas in Paris – Jay-Z and Kanye West (2011)

Leave it to Kanye West and Jay-Z to combine street fashion swag with the couture capital of the world. Both Ye and Z have been among the foremost game-changers in the relationship between music and fashion. Starting out as iconoclasts, they’ve broken down the stuffy barriers of elite fashion and transformed it into a more inclusive, representative community that also reflects urban perspectives: they’ve changed luxury fashion from the bottom up and created a permanent space for hip-hop during fashion weeks. ‘Niggas In Paris’, from the 2011 collaborative album Watch the Throne, is a homage to both hip-hop and couture. ‘What’s Gucci, my nigga? What’s Louis, my killa? What’s that jacket, Margiela?’ the wordsmiths rhymed. Before this song, not many people outside the fashion industry had even heard of Margiela. They have now and Kanye has become the brand amabassador for Balmain (see their collaborative music video).

3. Fashion – David Bowie (1980)

Leave it to the late David Bowie to question the authoratative nature of fashion by comparing it to fascism in ‘Fashion’, from his album Scary Monsters (and Super Creeps). We’ve all wanted to be part of the it crowd at some point, but Bowie warns about the potential militancy of slavishly following trends. ‘Fashion! Turn to the left. Fashion! Turn to the right. We are the goon squad and we’re coming to town,’ he sings. Thankfully the days of top-to-bottom fashion are over and the industry has evolved to become more democratic – a movement that Bowie himself helped to spearhead. ‘Beep Beep’.

4. Fashion Killa – A$AP Rocky (2013)

The video and lyrics of ‘Fashion Killa’ are fashion-focused in a very literal way. Essentially, A$AP Rocky and Rihanna go on a shopping spree and drop rhymes about brands, such as ‘I crush down with that top down, bossy see how I ride ’round. Mami in that Tom Ford, Papi in that Thom Browne. Rick Owens, Raf Simons, boy she got it by the stock’.

5. Lifted – CL (2016)

The ladies of K-pop/hip-hop group 2NE1 are instrumental fashion figures – especially their leader CL, who’s a fixture at fashion week, sitting next to Rihanna and Nicki Minaj, and hanging out with Marc Jacobs, Riccardo Tisci and her bestie, Jeremy Scott. CL is on the up and up, and she recently dropped the single ‘Lifted’ as part of her solo debut/infiltration into the US pop landscape. CL might be the first Asian artist capable of breaking into the tough market because she’s got swag and, most importantly, ‘gold on my necklace, gold on my wrists. Girls gettin’ mad cause their boys want a kiss. You don’t know me, and you don’t know my style. Gettin’ lifted, never coming down’.

Get the outfit that rappers rap about and singers sing about at  Shop The Boulevard

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