“The women in my family could sit and argue the merits of a slingback versus a peep-toe for hours,” he says. “I was the only child in this whole circle of adults, and I became the shopping companion. I had very strong opinions.” At the age of 5, he redesigned the wedding dress (“Too many bows!” he complained) that his mother wore to marry his stepfather, Bill Kors, the man who adopted him later that year. (His parents had divorced when he was 2.) In the fourth grade, he wore a “Russian Cossack tunic” to school.
The only detour he took from fashion involved some acting classes in Greenwich Village when he was about 13. “I had Broadway fantasies,” he says. “But then I realized that what I loved about going to acting school was being in Manhattan, and that the minute I left class all I wanted to do was go shopping. And that was it. The final decision was made.”
He opened a shop in his basement called the Iron Butterfly, where he sold tie-dyed shirts and miles of macramé. He hired himself out to do caricatures at bar mitzvahs, and in the evenings he managed a local tennis club. “All the women would come to play and they’d miss half their game because I’d be sitting there chatting with them. It was like, Oh my God I want to redo my mink coat—what should I do?” The club’s owners noticed his interest in fashion and his gift for bonding with the members, and asked him why sales in the pro shop were so poor. “I was like, ‘The women here are great-looking and hip and you’re selling clothes from 25 years ago. Let me re-merchandise it.’ ” So they did. “And the next thing I knew, I was off to F.I.T.”
But Kors was restless, itchy to get into the world of selling clothes rather than thinking about them. “I knew what kind of clothes I liked, and to sit and sketch them just seemed boring to me.” So he found a job as a salesboy at Lothar’s, a trendy store on 57th Street. “You got two free outfits a season,” he says. “Done! Sign me up!” He dropped out of school, and within months had full command over Lothar’s: He designed the store’s private label, he decorated the windows, he oversaw the staff. “I had three seamstresses,” he says. “If it was raining on Monday, I’d run down to 40th Street and we’d have raincoats by the end of the week.”
“Women say, ‘I wish I was French. They know how to tie scarves!’ ” Kors rolls his eyes.
One day, Bergdorf Goodman’s then–fashion director Dawn Mello saw Kors in the window of Lothar’s assembling a display. She knocked on the glass and asked him, “Who makes these clothes?” He said he did. She said, “When you have your own collection, call me.”
“I literally ran home to start a collection,” Kors recalls. The buying team at Bergdorf liked what they saw, and they placed an order. “The first thing I said was, can I please do a trunk show?”
Kors loves trunk shows. Even now he does about one a month in locations ranging from Dallas to Greenwich to the Costa Mesa Mall, though his mother, Joan, who is the brand’s “West Coast Ambassadress,” often handles that market herself. He knows his best customers by name. He meets their daughters and granddaughters, and he dresses them as well. “I have a client who is 81 years old,” he says. “Her name is Banana Reily, and she lives in New Orleans. She’ll buy a sable-collared double-faced coat and be like, ‘I’ll turn the air conditioning up, it’ll be fine!’ Oh, she’s just the best. Her family owns the Tabasco-sauce business, so she’s the hot-sauce queen.”
Kors, unusual among designers, likes to listen to his customers. He likes to hear what they’ve liked, what they hated, what chafed when they walked down the block. “I think empathy is a big thing,” he says. “I think a lot of designers don’t put themselves in the consumer’s place. And I’m like, Someone’s got to take out their credit card and buy it. Do you really want it? Are you not going to beat yourself up after you bought it?”
He has had his misses, moments when the references to the classics looked costumey and odd, or when he veered too far from the vocabulary he knows best. His Fall 2000 collection, for example, was a big-city homage to the designer Bill Blass: red lipstick, Gershwin tunes. He was slammed by the press, though it sold quite well. “I always like something familiar and something unfamiliar together. When it’s totally unfamiliar I need a road map, and I don’t think people shopping want to think that hard. And when it’s totally familiar, well then it’s a commodity. It’s a Band-Aid. The joy is missing. Over the years we’ve had collections that are, Oh God, Hamburger Helper again?” And so he walks the line, continually trying to make modern the things we already know.