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Thinking ahead or behind 10, 20, even 50 years

Top Designers of the 1990s Gianni Versace, Prada, Dolce & Gabbana, Rifat Ozbek, Marc Jacobs for Perry Ellis, Anna Sui, Romeo Gigli, Alexander McQueen, Calvin Klein, Fendi, Hussein Chalayan, Tom Ford for Gucci, Martin Margiela, Dries Van Noten, Ann Demeulemeester, Vivienne Westwood, Comme des Garons Rei Kawakubo, Yohji Yamamoto, Donna Karan, John Galliano, Karl Lagerfeld for Chanel, Yves Saint Laurent, Theirry Mugler, Christian Lacroix, Jean Paul Gaultier, Ralph Lauren, Bill Blass, Stephen Burrows, Oscar de la Renta, Anne Klein, Sonia Rykiel, Missoni, Chlo, Kenzo, Issey Miyake, Giorgio Armani, Valentino, Betsey Johnson, Zandra Rhodes, Bob Mackie, Helmut Lang, Julien MacDonald, Richard Tyler, Isaac Mizrahi, Michael Kors, Christian Francis Roth, Moschino, Alaa Mens Trends of the 1990s Giorgio Armani maintained the position as king of tailoring for men who were looking to suit up but as the 1990s was the most casual decade yet, many men were looking to indulge in the permission society had given them to be more laid-back

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MORE: Come See What Happens When a Grown Man Dresses Like Prince George for a Week Riley is the designer responsible for some of George's cutest outfits (and the ones most similar to styles his dad sported when he was younger)