From Versace to the Gap, a chronological look back at the fashion campaigns fronted by the legendary entertainer. Label: Versace Season: Spring 1995 Photographer: Steven Meisel Celeb Spotting: When Gianni Versace cast Madonna as the star of his SS95 adverts, the designer was setting a new standard in fashion advertising that has ruled ever since: The celebrity as model. Sure famous women had posed in glossy mag editorials ever since Diana Vreeland’s days at Vogue, but never before had one been tapped for such a massive commercial campaign. The glamorous, retro images feature Madge as an old school Hollywood goddess, lounging poolside wearing plunging Marilyn dresses and pin-up bikinis, a play on her monster smash hit, ‘Vogue’. Label: Versace Atelier Season: Fall 1995 Photographer: Mario Testino Super Mario: Even though Madonna had specifically requested Testino to shoot her second spread for Versace, the prolific (but not yet well-known) fashion photographer was still nervous to work with the icon. ‘I could not just walk in and tell her what I wanted to do,’ he once recalled. ‘She had always controlled her own image. But I thought that if she had asked for me, she wanted my way of seeing her.’ When the advertorial ran in the fall of ’95, it was tagged with the bold, red headline, ‘Versace Presents Madonna Photographed by Testino’, sending the photographer’s career into orbit. ‘I was told that it would change my life to photograph Madonna. I did not realize to what extent.’ Label: The Gap Season: Fall 2003 Photographer: Regan Cameron Fall Into The Groove: In the early 2000′s, the Gap had fallen on hard times and in an effort to lure customers back to their stores, the company enlisted celebrities to appear in their ads. The plan worked as sales improved in 2002. The following year, they nabbed Madonna, hoping her presence would further increase Gap brand awareness, especially amongst the 30-40-something demographic. After pairing her up with hip hop star Missy Elliott, the duo posed for a series of print ads — where Madge accessorized her beater-T and blue cords with a pricey stack of Neil Lane diamond bracelets — and filmed a music video-style TV commercial using a mash-up of Madonna’s ‘Hollywood’ and ‘Into the Groove’. Label: Versace Season: Spring 2005 Photographer: Mario Testino She’s Gonna Make it After All: Ten years after she first sauntered in front of Testino’s camera for the sake of Versace, Madonna came back for a return engagement. This time around, the theme was ‘women in the office’ in which Madge was kitted out as a Mary Richards for the aughts. The behind-the-desk setting, pencil slim dresses, flared trousers, and big hair all recalled the 70s-era working girl. House creative director Donatella Versace explained her decision to cast the superstar thusly: ‘Madonna represents a modern executive woman who has great style and flair. Not only is she in control of her career but also of her fierce wardrobe.’ Label: H&M Season: Spring 2006 & 2007 Photographer: John Rankin (2006) & Steven Klein (2007) If At First You Don’t Succeed: In 2006, H&M supplied Madonna and her “Confessions Tour” crew with a set of tracksuits to be worn off-stage. But when they were also sold at H&M stores, sales of the cheap-o polyester Juicy Couture knock-offs tanked. However, that didn’t stop the Swedish mass marketer from trying again. So later that year, they announced that this time, Madonna herself would be involved in the design process, with the star and retailer collaborating on a line called M by Madonna. The collection — featuring high-waisted pencils skirts, deep-v necklines and kimono dresses in simple black and white — was much more well-received by customers and helped to boost H&M’s profits in 2007 Label: Louis Vuitton Season: Spring 2009 Photographer: Steven Meisel Feathers & Fishnets: After attending a ‘Sticky & Sweet’ concert in late 2008, LV creative director Marc Jacobs decided to ask Madonna to front the brand’s SS09 ad campaign. And all it took was an email for Madonna to oblige. The Parisian-bistro themed photo-set — shot at Figaro in Los Angeles — is a lavish roar of textures, prints and colors, but harkens back more to Toulouse-Lautrec than modern French style. It was rumored that Madge received a $10 million paycheck for playing Louis Vuitton muse, a figure that communications director Antoine Arnault emphatically shot down, calling it “Absurd.” Label: Louis Vuitton Season: Fall 2009 Photographer: Steven Meisel Solar Perplexed: Madonna, Marc and Meisel teamed up one more time in 2009 for the Autumn/ Winter Louis Vuitton campaign. And when Madge showed up at the Met Costume Gala that May wearing a poufy blue micro dress, can-can boots and bunny ears, she gave the world a sneak peak at the goods. However, when the photos were unveiled, they were met with some serious side-eye rather than applause — Madonna was hardly recognizable in the obviously altered images, which were ‘solarized’ for artistic effect. When un-retouched outtakes from the session were ‘leaked’, yet another international debate on the virtues of Photoshop ensued. Label: Dolce & Gabbana Season: Spring 2010 Photographer: Steven Klein So Dishy: The Madonna/ D&G connection goes all the way back to 1991, when the singer referenced the designers in her hit documentary,Truth or Dare. Subsequently, Domenico and Stefano were tapped to create costumes for her 1993 ‘Girlie Show’ world tour. But it wasn’t until 2010 that she posed for an ad campaign, where a very domestic Madonna played the part of “Italian housewife”. (On the session, Stefano quipped, ‘It was fun…Has anyone ever seen Madonna washing dishes?’) In tandem with this commercial coup, Madge “designed” a six-piece collection of sunglasses under the label MDG for Dolce & Gabbana, released in June 2010.