(Photo: Tina Barney)

To understand the way Andy Spade works, consider this tale of retail alchemy:

Engaged by J.Crew in 2008 to reimagine that company’s approach to menswear, Spade and his partner, Anthony Sperduti, suggested putting a J.Crew shop in an out-of-business Tribeca bar called the Liquor Store, which still had its vintage sign out front. They insisted that no J.Crew sign replace it and that the original bar remain, with the register behind it, and that the mantel be decorated with toy soldiers from Andy’s personal collection. Music must come from a stereo whose dials and knobs would be visible to customers, and the speakers should emit just enough crackle to remain credibly lo-fi. There should be three colors of a T-shirt, say, rather than eighteen. Inside the closet-size dressing rooms, there should be “exhibitions” by downtown artists and photographers. There should be books chosen from the Strand, and a mug full of pencils munched on by famous writers (like Max Blagg) for sale as well. The staff shouldn’t come from the world of retail, but preferably from the world of art or high design.

J.Crew did it all—a massive departure for a company whose stores are mostly in shopping malls. According to J.Crew creative director Jenna Lyons, the Liquor Store “far exceeded” expectations. “Far, far exceeded!”

Andy Spade’s explanation, the key, he says, to his marketing success?

“The bigger you get, the smaller you act.” By which he means: The more personal a brand, the more stuff it can sell.

Andy Spade is the lesser-known half of a great New York power couple, with their fairy tale of homegrown megasuccess. In 1993, Spade’s college sweetheart, Kate Brosnahan (as she was named then), returned home from her job at Mademoiselle magazine to the small apartment the couple shared with an idea for a handbag that was simple, functional, and not a million bucks. The bag would be a perfect rectangle of ripstop nylon with a webbed nylon strap. Its only adornment, in the end, was a little KATE SPADE NEW YORK label sewn on the exterior.

Andy Spade was working at an advertising agency in those days, and he had some ideas for how to sell Kate’s bag. (First idea: Call the company Kate Spade, which was not, yet, even her name. “He’ll never marry you now!” moaned Kate’s Irish Catholic mother down the phone from Kansas City, but no one could deny that it did sound nice.) He gutted his 401(k) account of its $35,000, and Kate got to work. “I was super-conservative,” Kate says, remembering those early days, “and Andy was like, you should just do it!” The couple ate a lot of cheeseburgers—it would be years before Andy’s credit was good enough for an American Express card again.

But it worked. In 1993, the business did $100,000 in revenues; in 1995 it did $1.5 million, and Andy felt he could finally quit his day job as a creative director at Chiat Day. Kate’s two best friends, Elyce Arons and Pamela Bell, joined the company. They referred to Andy as “Charlie,” themselves as “the Angels.”

Handbags are never really about the nylon, the leather, the pockets, or the straps. Once you have all those things and they are all working together and looking nice enough, handbags become about the house you wish you lived in, the film star you most admire, the music you’d like other people to think you like. “If you look at everything that was going on in fashion at that time,” Andy says now, “there was not a voice that just said hi or hello. There just wasn’t a lot out there that looked real. But there’s something great about suburbia. There’s something great about innocence. A Peter Pan collar is sexier than a bustier.”

In 1998, Andy launched a collection of similarly simple bags for men called Jack Spade—messenger bags for grown-ups, really. He didn’t want to use his own name so he chose Jack, because there have been so many good Jacks over the years, like Kerouac and Parr.

A few months later, the Spades sold 56 percent of the two companies to Neiman Marcus for $34 million and agreed to stick around to creative-direct the company.

But then in 2006, Neiman Marcus decided to sell Kate and Jack Spade, and the Spades, trying to suss out their own next move, conducted an experiment: They would count the number of decisions they were called on to make in the course of one day. How many times would they have to sign off on the length of a zipper or the number of rhinestones on the toe of a patent-leather shoe? Which is the best shot for the ad campaign? Who should be the new assistant to the assistant of the head of PR? What color ribbon should wrap around which color stock on these very tasteful thank-you notes?