In honor of Fashion Month — which kicked off in New York on Sept. 4 — we look back on the love affair between hit-makers and designers, including sightings, controversies and, of course, Madonna's boobs.

20. Janelle Monae Rocks Rebecca Minkoff (2014)

Soulful R&B diva Janelle Monae took center stage at Lincoln Center in 2014, performing new songs on stage during Rebecca Minkoff's runway show. "I&lsquom a fan of Rebecca’s work; she pays such close attention to detail,” Monae told Billboard after the show. “I actually almost forgot my lyrics during the performance because I saw these amazing pair of shoes!”

19. Gwen Stefani Debuts L.A.M.B. (2006)

Gwen Stefani channeled her dynamic style and love of punk and Harajuku Girls to create her first fashion line, L.A.M.B. Filled with rasta-inspired threads, bikini tops, pleated skirts and funky T-shirts, Gwen’s fetishistic skater-tinged line was unleashed on the fashion scene back in 2006.

18. Francoise Hardy at the YSL Show in Paris (1969)

French actress and singer Francoise Hardy might not have seemed prime material to be the first real “It" girl, but in 1969, the 25-year-old queen of the ye-ye girls — those Parisian pop naifs — was the first pop star to sit front row at a runway show. Her appearance at the YSL Couture show in Paris made all the dailies, thus inaugurating the era of the boldface front-row spectacle.

17. Sonic Youth Rocks the Marc Jacobs Show (2008)

Marc enlisted the musical assistance of his longtime pal Kim Gordon of indie rock band Sonic Youth for his grungy, Fall 2008 runway show. Marc has always had a flair for uniting music and fashion. In 2009, the designer had Lady Gaga perform at his Spring 2010 afterparty and got Madonna to front the 2009 spring Louis Vuitton ads.

16. Florence Welch Performs in a Giant Seashell at Chanel (2012)

What is a better pair than Florence Welch and Chanel? The ethereal, British singer’s cosmic voice stunningly blared in Paris' Grand Palais as Karl Lagerfeld revealed his under-the-sea inspired spring 2012 collection, which was perfectly punctuated by the giant white seashell that housed the pearl of a diva.

15. Grace Jones Struts (1985)

Actress, model and musician Grace Jones owned the year 1985. She starred in A View to a Kill, had a hit song with “Slave to the Rhythm” and posed naked in Playboy with her boyfriend, Dolph Lundgren. But she also encapsulated all that was good about &lsquo80s fashion and music when she walked in the A/W Paris fashion show of her friend, the great French-Tunisian designer Azzedine Alaia.

14. NSFW: Madonna Walks Topless in Jean Paul Gaultier’s Show (1992)

Though technically outside the confines of the official Fashion Weekdom, Madonna’s topless strut down a runway in Los Angeles during Jean Paul Gaultier’s 1992 amFar fashion show ranks among the most iconic moments in the history of fashion, music or breasts.

13. Musical Chaos at Michael Kors (1991)

Perhaps the most seminal of all moments in fashion history took place on the second day of Fashion Week in New York City in 1991. The New York loft where Michael Kors was showing his collection was sweaty and packed. As his models walked the runway, the Jacksons’ 1978 hit "Shake Your Body (Down to the Ground)" shook the building. So hard, in fact, the ceiling collapsed. The powerful fashion editor of the International Herald Tribune, Suzy Menkes, was bruised. New York Times editor Carrie Donovan was rattled. Fern Mallis, the creator of New York Fashion Week, who had just started her job at CFDA at the time, recalls, “It was the shot from Sarajevo that started the war.” Mallis resolved to centralize and modernize Fashion Week. Hence, the famous tents at Bryant Park that debuted the following year, sans ceiling plaster.

12. Lady Gaga Brings “Bad Romance” to Alexander McQueen’s Show (2009)

Accompanying the encore of Alexander McQueen’s mysterious and ethereal Spring/Summer 2010 collection, the world was introduced to Lady Gaga’s “Bad Romance” for the very first time. (And for those that didn’t know, the collection was also the source of Gaga’s Armadillo heels, which were later made famous through the song's video.)

11. Rihanna Storms Paris (2014)

Kanye West is there. Katy Perry is there. Rita Ora is there. But the only person anyone is talking about at Paris Fashion Week 2014 is Rihanna. Balmain, Lanvin, Dior, Gaultier, Givenchy, Stella McCartney — the only place she isn’t is Balenciaga (she got caught in traffic). How could one musician suck out all the oxygen in Paris? Easy: Credit her voluminous and incessant Instagramming.

10. Diddy Designs (1998)

Just as the four-minute mile was impossible until suddenly Prefontaine proved it wasn’t, so too did Sean Combs (aka Puff Daddy aka P. Diddy) prove that a musician could helm a serious fashion line. In 1998, he launched Sean John sportswear, showing at New York Fashion Week that year. In 2004, he won the prestigious Perry Ellis Menswear Designer of the Year Award and, in so doing, cleared the way for Gwen Stefani’s L.A.M.B. line and certain Spice Girl.

9. Posh Spice's Walk of Fame (2006)

It was Milan, 2006, and Victoria Beckham had not yet fully realized her own fashion ambitions (her eponymous label would launch in 2008). But when Posh Spice closed out Roberto Cavalli’s men's show in a white silk gown and gold stilettos, she put the fashion world on notice she meant business.

8. Guns N' Roses Rock the Rose Bar for NYFW (2010)

Guns N' Roses staged a late-night secret show for New York Fashion Week in 2010. The rough and rowdy band played their anthemic hits — including "Paradise City" and "Welcome to the Jungle" — in a tiny private venue at the Rose Bar for stylish, A-list attendees, including members of The Strokes.

7. Grace Jones and Chaka Khan Perform at the Etam Fashion Show (2012)

For their spring 2012 show, the Parisian lingerie label Etam created a diva-packed lineup. Music icons like Grace Jones, Sister Sledge, Gloria Gaynor, the Pointer Sisters and Chaka Khan hit the stage to both model and perform during the event.

6. Babs Front Row at DKNY (1993)

For her first Fashion Week in 1993, Donna Karan invited the New York City Church of Christ gospel choir to belt out "Are You Ready for a Miracle?” But the real musically noteworthy moment here is Barbra Streisand, whose very noted appearance in the front row did for American musicians what Hardy did for French ones 25 years earlier.

5. Kanye West Debuts Fashion Line in Paris (2011)

Kanye West made his Fashion Week debut back in 2011 before a glittering crowd that included Alicia Keys, Swizz Beatz, P. Diddy, Lindsay Lohan, Jared Leto and Ciara. Unfortunately, not even the swanky afterparty, featuring performances by Azealia Banks, Common, Mos Def and Big Sean, spared the show from the harsh reviews it received.

4. The Strokes Perform at Tommy Hilfiger's 25th Anniversary (2010)

Back in 2010, the Strokes brought their raw and textured beats to Tommy Hilfiger's posh 25th anniversary bash. The band performed hits like “Last Night" to guests that included Christina Hendricks, Kelly Osbourne, Jeremy Piven, Bradley Cooper and Jennifer Lopez.

3. Liza Minnelli and Josephine Baker at Versailles (1973)

The 1973 Battle of Versailles pitted five American designers — Bill Blass, Stephen Burrows, Halston, Oscar De la Renta and Anne Klein — against five French couturiers: Yves Saint Laurent, Christian Dior, Hubert de Givenchy, Pierre Cardin and Emanuel Ungaro. Predictably, more was at stake than simply fashion. The French trotted out Josephine Baker to do a snazzy number on the runway, while the Americans were accompanied by Liza Minnelli singing “Bonjour Paris.” Heureusement, the Americans triumphed.

2. Duran Duran Performs at Milan Fashion Week (2011)

Back in 2011, Duran Duran took Milan Fashion week by storm. The band was presented with a style award by the mayor of the town, had Vogue Italia's Franca Sozzani throw a dinner party in the their honor, attended the Versace show and played at the aftershow party in a theater in Milan. The band wound up getting more fashion week action than some fashion editors.

1. Kiss in Milan at John Varvatos (2014)

Kiss frontman Gene Simmons might not be everyone’s cup of tea, but one can’t argue with the sensation the 40-year-old band’s unannounced performance caused at John Varvatos’ Milan Fashion Week performance. Was it the best moment of fashion and music? No, but it might have been the loudest and sometimes that’s all that counts.

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