Amber Valletta first met Karl Lagerfeld during a Chanel fitting in the early ’90s. The 18-year-old supermodel-in-the-making felt an instant connection with the inquisitive creative director, who asked her personal questions to put her at ease and then became serious when she walked through the salon in his latest designs. “It was typical iconic Karl, waving his fan and talking about such interesting things,” recalls Valletta of their initial tête-à-tête in Paris. Years later, when her luggage got lost during a trip to Europe, it was Lagerfeld who outfitted her in looks from his namesake brand. “He was always so generous,” she shares, adding that her classic Karl Lagerfeld blazer, which emulates his own crisp, monochromatic style, and her sweet Choupette sweater, an ode to his beloved cat, are wardrobe binders Valletta still wears to this day.