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A color-blocked leather jacket with a giant black-and-white eight ball on the back, designed by Michael Hoban in 1990 and priced around $800. For two winters it was the status symbol of New York, worn by ballplayers and rappers, robbed off kids' backs, and then dropped so hard that Seinfeld put one on Puddy as a joke.
Expedition outerwear became high-school currency. The North Face started as a mountaineer's brand and somehow became the cold-weather uniform that separated the haves from the have-nots—a puffy jacket and fleece that climbed from base camp to your hallway.
Starter's nylon and satin team jackets were the uniform of 90s cool — oversized windbreakers emblazoned with NBA and NFL team logos that transformed playground basketball courts and city streets into stadiums of style. Starter jackets became so coveted they sparked robberies, making them perhaps the decade's most dangerous fashion statement.