Every designer’s dream is to create something so stylish it transcends fashion and becomes a classic: the Gucci loafer, the Burberry trench coat, the Hermes bag. Creating something iconic is only half the battle; it’s what comes next that counts–the tweaks that render these things as cool today as they were the year they were created. When Coco Chanel–above, circa 1926–died in 1971, her classic tweed jacket could have died too. She herself had kept the look alive for more than five decades. How much longer a life did a thousand-dollar jacket deserve? Ask Karl Lagerfeld. In the 20 years he has been designing the label, he has reinvented the jacket for society women and rap stars alike. TIME’s Lauren Goldstein presents the evolution of a classic: ’36 TWEED INDEED Even though she was a snob, Chanel loved tweed. The fabric was cheap, but she used the Duke of Westminster’s factory and lined the jacket in fur to up the cost–and the status. ’38 FITTING IN The stock-market crash changes everything: clothes become more formfitting and Chanel follows the trend, cutting her jackets with tight waists and full shoulders. ’55 SLOUCH CHIC The shrugged-on silhouette came from Coco’s first big idea of taking a lover’s sweater, cutting it down the front and sewing ribbon on the edging. ’60 COCO’S CLASSIC The contrasting-trim look emerges in 1955 and continues as a classic into the 1960s, when Chanel’s suits become de rigueur for the ladies who lunch. ’66 THOROUGHLY MOD MADEMOISELLES Chanel detested miniskirts. She found the knees to be the most unattractive part of a woman’s body and insisted that all skirts fall just below. Of course, in 1966, while Pierre Cardin and Paco Rabanne dominate the fashion headlines, Chanel can’t stop guests at her haute couture show at the rue Cambon salon in Paris from displaying lots of leg. ’69 FLYIN’ HIGH Model-actress Marisa Berenson wears a tweed suit , the ultimate symbol of status and wealth, circa 1969. ’70 LOST DECADE After Chanel’s death in 1971, the studio is led by her former assistants. Cheryl Tiegs and Catherine Deneuve are hired to jazz things up, but it doesn’t work. ’86 POWER look “Chanel established a look that is for our century what the two- and three-button suit is for men,” Lagerfeld said in 1989. The tweed suit comes back into power in the ’80s. ’90 HANG 10 Lagerfeld surfs past the competition by combining the language of Chanel with the patois of the street and cutting the jacket into surf-inspired shapes. ’95 COCO LOCO Lagerfeld appeals to rappers like TLC’s late Lisa Lopes, left, and Rozonda Thomas, who delight in the modern take on the Chanel jacket: the Windbreaker. ’96 I, CLAUDIA Just when the Gap thought it had cornered the market on cool, Claudia Schiffer–a longtime Lagerfeld favorite–stalks Chanel’s runway in a pair of khakis. ’01 DETAILS, DETAILS Chanel was a nut about armholes, but she never felt she got them right. Celebrities like Gwyneth Paltrow take to Chanel’s tiny tweed jackets at the turn of the century.