In footwear folklore, women have Cinderella's glass slippers, Dorothy's ruby shoes and Carrie Bradshaw's cache of Manolos. Men have O.J. Simpson's Bruno Maglis, shoe bomber Richard Reid's explosive high-tops and Nikita Khrushchev's legendary Cold War shoe tantrum at the United Nations. • Not surprisingly, shoe shopping scores low as a favorite male pastime. But sooner or later, sole-searching becomes unavoidable. To make the chore a little less painful, we asked fashion gurus, foot doctors, shoe merchants and shoppers for tips on landing a stylish, high-caliber pair of men's dress shoes. • The simplest method is to outsource the job. "I leave it up to my wife because she has a keen sense of style," says John Mackey, a 51-year-old freight sales rep from suburban Seattle.
It's a common tactic. Former shoe-shopaphobe Stephen Duffy, 29, a jury consultant in Costa Mesa, Calif., used to rely on female relatives for guidance as well. "I started out as a typical guy — totally afraid of it," he says. But after working as a bartender, on his feet all night, Duffy developed an appreciation for quality shoes and slowly learned how to find them.
In some ways, shoe hunting is like buying a car.
Step 1: Take a test-drive
In a typical day of walking, human hooves endure several hundred tons of force, doctors say. And ill-fitting shoes are the villain behind one out of six Americans suffering corns, calluses and other ailments.
Dr. Dennis Frisch, a spokesman for the American Podiatric Medical Association, recommends starting with a few basics. Get measured, shop in the afternoon (feet swell during the day), try on both shoes and buy the size that fits your larger foot. Also, make sure you can wiggle your toes and have three-eighths to half an inch between the longest toe and the end of each shoe.
Avoid shoes that feel like they need "breaking in," Frisch cautions. Although fine leather requires several wearings to soften and mold to the foot, a shoe that's painful in the store is probably bad news.
"Try different styles and sizes," he advises. "To find the right fit, you have to invest time."
Step 2: Avoid sports cars
Once upon a time, about 400 years ago, men wore shoes that rivaled anything donned by women. They strutted in high heels decorated with jeweled buckles and colorful embroidery, says Elizabeth Semmelhack, curator of the Bata Shoe Museum in Toronto. The Enlightenment brought an end to that. The emphasis on rationality led men to abandon their inner Elton Johns, she says. To this day, "men are afraid of fashion because it connotes femininity."
On the plus side, that makes choosing color and style a snap. Meghan Cleary, an author who bills herself as America's shoe expert, says black and brown control the color spectrum, and laceups trump slipons "if you want to be taken seriously" in the business world. She encourages men to experiment with colors, but in understated ways, such as black wingtips tinged with deep auburn or deep green hues, or hand-burnished for a different texture.
Cleary rates cap-toe, wingtip and split-toe designs as a virtual photo finish. All are fashionable, she says.
Step 3: Check the tires
Choosing a sole — leather vs. rubber — is trickier, the footwear equivalent of Mac vs. PC.
"Old-school thinking is that leather is dressier," says Dennis Daniels, a shoe salesman at Garys, an upscale Newport Beach, Calif., shop. "You don't want a big old tire tread on your foot when you walk into a boardroom."
But synthetic soles have legions of fans, partly for their traction on slick surfaces. For the indecisive, Cole Haan offers a hybrid: leather-soled Italian shoes with Nike Air technology hidden inside.
A related debate centers on sole thickness. Thin is considered more fashionable but is not always practical.
"If you mostly sit at a desk, thin soles are fine," says Frisch, the podiatrist. "But if you get off the subway and walk 10 blocks every day, the shoe is going to hurt and wear out sooner."
Step 4: Examine the upholstery
History's most durable footwear appears in the Old Testament: God marched the Israelites through the desert for 40 years but their sandals never wore out, according to the Bible (Deuteronomy 29:5). Modern cobblers can't match that feat, but they have created other unusual products. New & Lingwood, a British shoemaker, sells $1,600 loafers crafted from Russian reindeer hides found aboard a 1786 shipwreck and cured in baths of oat flour, wood liquor and seal oil.
Other exotic skins include ostrich, crocodile and peccary. Most don't hold up like calf leather, generally regarded as the gold standard for dress shoes. But even calfskin has skeptics.
"My shoes are cow leather, not calfskin, pigskin or deerskin," says Kenneth van Dissel, who sold footwear in college and now works as director of engineering at South Coast Plaza. "The other skins don't fare well in an industrial environment, where my job takes me. My shoes go from plant floor to boardroom. My highest regard is for cordovan (horsehide) shoes. They last decades."
Step 5: Look under the hood
Beyond quality leather, craftsmanship is the surest sign of luxury footwear. Eye the stitching on the sole and upper for precision. Be sure the insole is all leather, which wicks away perspiration, lets the shoe breathe and molds to the foot. The inside back of the shoe should be a rougher material, such as suede, to grip your heel as you walk.
Other flourishes can include brass nails in the sole, and heels with a dovetailed piece of rubber that can easily be replaced when the back wears down.
Ask the salesman if the shoe features welt construction, in which the sole and upper part of the shoe are stitched to a center strip of leather. Welting enables shoes to be resoled, extending their life.
Step 6: Cost and maintenance
All our experts agree that you truly get what you pay for with footwear — up to a point. The summit of shoedom — custom shoes such as John Lobb's $6,200-plus designs — are "great for people with a difficult fit, but the average person doesn't need them," Frisch says.
So, what is a reasonable price for top-notch dress shoes? Frisch says $75 minimum, but Daniels suggests at least $200 for high-quality calf leather. And Cleary goes higher, estimating $400 to $500 for corporate-caliber footwear.
Cleary's dream brand is Dries Van Noten, a Belgian designer. Other panelists place Bontoni, Ferragamo, Cole Haan, Artioli and Prada in the shoe stratosphere. But most rate John Lobb — the footwear worn by James Bond in 2006's Casino Royale — as No. 1. Entry-level prices for these brands range from about $150 for low-end Cole Haans to $1,120 for John Lobb's cheapest off-the-shelf model.
Duffy says he used to blanch at such prices, until he did the math: "You can buy a cheap pair that needs replacing every year, or one good pair that's going to last."
Cedar shoe trees, leather creams and resoling can extend the life span of pricey foot duds to a decade or more, experts say. But there is a catch. You need to buy at least one other pair and rotate wearing them, according to the podiatrists' group. Leather needs to breathe, and using the same pair every day will wreck them.
But there's no need for a shoe closet as big as Manolo-holic Carrie Bradshaw's. Even Barack Obama owned just two pairs of dress shoes during the presidential campaign.