Prince was self-conscious about his height — 5'3" — and wore high-heeled boots (either 4" or 3 1/3") whenever he went out in public, and moreover, he did not like to be seen wearing the same pair of boots at two different appearances on the same day.
Prince contracted with Andre No. 1, a famous cobbler-to-the-stars on Sunset Boulevard founded by Andre Rostomyan, whose client roster includes everyone from Frank Sinatra to Lady Gaga. Rostomyan made a shoe last — a wooden model — of Prince's feet, and would take orders for 30-40 pairs of boots/month, eventually supplying more than 3,000 pairs to Prince.
Each pair was identical in shape, but used unique mixes of materials, colors, and gimmicks like light-up lucite heels. Prince consulted closely on the details, visiting the store in person with fabric, making calls as to whether to cut it with or against the bias, etc. Boots that were to be worn onstage — where Prince gave incredibly athletic, graceful performances — got extra-strong structural wood to ensure that they could survive the workout that Prince put them through.
Prince refused to have his wooden lasts improved by means of a 3D scanning system, saying that the religious tenets of the Jehovah's Witnesses forbade believers like him from using technology to capture a part of the human body.
There was only one instance in which Prince was adamantly against something Gary suggested. "He was a Jehovah's Witness," the shoemaker explains. "I wanted to use one of the 3-D scanning machines I'd just gotten to mold the new shoe forms for him and make the process a bit faster, but he refused. I guess they don't believe in using technology to re-create a certain part of the body." Gary continued to make Prince's footwear by hand, even crafting "slippers" for him to wear while he was at home. "They were actually more like platform flip-flops," he says. "They looked a lot like those '90s platform thongs made by brands like Rocket Dog and Soda." Mostly, though, whether at home, onstage, or in public, Prince had his bespoke man stilts on. "I've seen a lot of people pull off a lot of different shoes, but there were definitely times where I thought Prince couldn't do it, especially with all of the splits and the dancing," Gary says. "But no matter the heel, he always did."
Meet the Man Who Made 3,000 Pairs of High Heels for Prince [Brooke Bobb/Vogue]