DENNIS GREENBAUM has a thing for heeled boots. He’s not a brazen rock star like Harry Styles or Rick James, careening across stages and strutting down red carpets in elevated shoes. He’s a retired 68-year-old in Maryland who used to work in ad sales and simply likes a lift. The attraction began with 1.5-inch-heel cowboy boots and evolved into a fondness for 2.5-inch Johnny Boots designed by Tom Ford for Yves Saint Laurent in the early 2000s. He contends they’re the most comfortable shoes he owns. “I have never been self-conscious about my height,” said Mr. Greenbaum, who stands at 5’7”. “But when I wear the heel, it’s impossible for me to slouch. You have to stand straight.” He especially enjoys that heels lend him a leaner shape—particularly when paired with high-waisted pants. “They elongate my whole body, which makes a difference in how I look in photos.”
According to Federico Barassi, the vice president of menswear buying for online retailer Ssense, Mr. Greenbaum is no outlier. “It’s encouraging to see people changing up the norms with [men’s] heels getting higher and higher,” he said, noting that designers have been elaborating on the cowboy boot’s loftier look.
Instead of rolling their eyes, modern men should consider reclaiming high heels. After all, we wore them first.
Despite their testosterone-rich associations with wranglers and rockers, heels have developed an inherently feminine reputation, which, even in today’s increasingly unisex fashion landscape, leads less-enlightened guys to scoff at the notion. Instead of rolling their eyes, however, modern men might want to consider reclaiming high heels: After all, we wore them first.
Elizabeth Semmelhack, the creative director and senior curator of the Bata Shoe Museum in Toronto, traced the genesis of high heels to the equestrian men of 10th-century Persia, who wore them to catch onto their stirrups. It wasn’t until hundreds of years later, when high heels came to Europe, that “women started to wear them to masculinize their attire,” she said.
After being worn by both sexes, heels were deemed an impractical choice for men and feminized during the Enlightenment. But hardworking guys, notably in the American Old West, continued to embrace them. Ms. Semmelhack has no problem finding similarities between cowboy boots and the 17th-century heeled riding shoes worn by men like King Louis XIV of France. She insisted that today’s men’s heels don’t point to “feminization, because they are quoting heels that were worn by men in the past.”
Fall offers plenty of sturdy-heeled men’s shoes that hark back to antique equestrian styles. For a statement, slip on Rick Owens’s “Kiss Chelsea Boots,” which rest on a nearly 5-inch platform heel inspired by Gene Simmons’s stage garb. For a less precipitous option, look to Dries Van Noten’s penny loafers, whose 2.75-inch heels can elongate the look of jeans.
While some mistakenly see heels as a cheat deployed by shrimpy guys, naturally tall men look better in them, too. Documentary host and producer Richard Faison, 31, is 6’2” and wears heeled boots with wide-leg pants to conjure a “’70s, groovy look.” Plus, he’s convinced they make him look like a model.
Mr. Faison, a Brooklyn native, started rocking heeled ankle boots by traditional American heritage brands like Frye in his early 20s after being denied entry into Manhattan night clubs for wearing Timberland boots. (Some venues across the U.S. still maintain this dress-code policy, one critics see as a covert effort to keep young Blacks out of upscale spaces.) “Discrimination will make you try some things,” he said with a sarcastic laugh. His friends didn’t understand the footwear at first. “My homies were like, ‘You’re dressing weird as hell.’” But he’s stayed with his heels—not only for their ability to get him past the velvet rope, but because they punch up his wardrobe. “It gives more edge to a formal outfit…But you can wear it with a T-shirt and jeans…It adds so much,” he said. “Women love the boots,” he added coyly.
Jasmine Benjamin, a Los Angeles stylist, pushes her clients toward boosted boots. She’s dressed crooner Miguel in sharp Cuban heels by Saint Laurent and songwriter Anderson Paak in stacked styles by Gucci. In her opinion, men’s heels are “the ultimate confident statement.” Considering they’ve been worn by kings, cowboys and rock gods alike, her argument can’t be dismissed.
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