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I searched but could not find a previous post of this column, so I don't know if this has ever been posted here--it is from 2005. If it has, then my apologies for the redundancy. I think it is a great read I have seen some of the misconceptions it corrects printed on this board. Enjoy.

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May Your Feet Grow Wings
A man, a shoe, an obsession

By John Kelly
Sunday, May 15, 2005; W18

I sing of shoes and the man, of boot and loafer and lace-up, of sneaker and flip-flop.
But of all of these shoes, I sing of one shoe in particular: stout of sole and firm of heel, the upper shot with tiny holes and edged in serrated leather, anointed on its toe with a curious medallion and marked over the instep by a sign, a sign as recognizable as the Z of Zorro or the ankh of the sun god Ra.1 See it? The symbol? From where you're standing it looks like a lazy W, but from where I'm standing -- looking down at the well-polished shoes on my feet -- it resembles a bird in flight about to flap its powerful wings and soar higher still.
I sing of the wingtip.
As for why exactly I sing of the wingtip, well, probably the best explanation is that I'm kind of weird that way. Why else would I spend the last few months walking around town with my eyes downcast, scrutinizing the feet of other men for wingtips, my head swiveling back and forth as if I'd dropped a quarter but didn't know where it had rolled to?
To me, anything worth being curious about is worth obsessing about. And what I have long been curious about is this: Why the wingtip? And also: How the wingtip, and how come, and where, and when?
Does this curiosity about the quintessential white-collar businessman's shoe make me a shoe fetishist? I don't think so. I don't parade around in front of a mirror, naked save for red latex stiletto-heeled, open-toed slingbacks that I store high on a shelf in my closet and keep shiny with regular applications of Windex buffed with a soft cotton cloth. I swear I don't. However, I do think a shoe can be a fetish, an object animated by a spirit that primitive peoples believe has a preternatural power to aid its owner.
Women slip their bunioned feet into strappy Manolo Blahniks in the belief that they are channeling Sarah Jessica Parker. Men buy Air Jordans with the subconscious hope that they'll be able to dunk. Ever since I graduated from college I've owned a pair of wingtips.
Good question.
'A Kind of Artless Shoes'
In 1773 the English writer Samuel Johnson visited some of the remote islands scattered off the west coast of Scotland. It was on the Isle of Skye, he wrote, that he first observed "the use of Brogues, a kind of artless shoes, stitched with thongs so loosely, that though they defend the foot from stones, they do not exclude water."
The shoes weren't unique to Scotland. Similar shoes were worn by the Irish, and brog in Gaelic simply means "shoe."
The distinctive feature of the shoes Dr. Johnson encountered were the holes.
Much lore has grown up around these holes, and many shoe-history sources say these peculiar perforations had a distinct purpose. Because Scottish and Irish peasants spent a lot of time tromping through bogs and creeks, this design feature seemed to make sense: No shoe of the time could keep your feet completely dry, so why even bother to try? Why not just punch the leather full of holes, allowing the water to run out after it had run in?
Alas, says shoe historian Sue Constable when I reach her by phone in Northampton, England, that story is apocryphal.2 "The English sense of humor has always picked a certain amount of fun at the Irish," Constable says. "I suspect that story comes from that, that only the Irish would be daft enough to punch the holes to let the water out." Constable thinks that even then the holes were a decorative element.
Those holes are called "broguing," and the British still call this type of shoe -- much modernized, of course -- a brogue.3 Scholars agree that this primitive Celtic shoe -- as different from what you can buy today at Nordstrom as australo-pithecine is from **** sapiens -- is the direct ancestor of the modern wingtip.
How did it evolve? I'll tell you, after a vastly oversimplified history of how, if you are a man, you came to be dressed the way you are.
A Vastly Oversimplified History of How, If You Are a Man, You Came to Be Dressed the Way You Are
In the days of Louis XIV, fashionable European men dressed as outrageously as women. They spackled their faces with makeup, defied gravity with massive powdered wigs, swathed themselves in bright embroidered fabrics and teetered atop platform shoes.
Back then, says Elizabeth Semmelhack, curator of Toronto's Bata Shoe Museum,4 "All kinds of bells and whistles were available to men in costuming."
Then came a little something called the Age of Enlightenment. When heads started rolling right and left, it didn't seem like such a good idea to pattern your dress after the monarch's. Men no longer wanted to look like what Semmelhack calls "effete, irrational aristocrats."
So here's what happens: Men abandon their high heels. They scrape off the makeup. They hold on to their wigs, but they tone them down a bit, replacing the towering hairscapes with more modest wigs that even a patriot such as Patrick Henry or Thomas Jefferson can wear. 5
The gentleman's standard article of clothing also goes through an evolution. No longer does the outfit hark back to the flamboyant attire a courtier wears around the palace. Instead, the model is the practical clothing an English gentleman wears on his country estate. This outfit is a tailored jacket and pair of trousers. In other words, a suit.
While the suit begins life as the outfit of choice for the landed gentry to wear on weekends, a sort of fashion trickle-down effect soon takes place: The non-landed and the non-rich take their fashion cues from the landed and the rich.
It is, says Semmelhack, "a double-edged sword." The middle class can show its aspirations by adopting the trappings of the upper class and donning the squire's suit. Soon, however, it's not optional. Not only may you dress in a suit, eventually you must. It becomes your uniform, and over time it loses any association it once had with afternoons spent tramping about a country estate, one or two hunting dogs in tow and a splash of claret awaiting your return.
Instead, it becomes the rigid carapace in which you wrap yourself for work. You are the man in the gray flannel suit, identical to every other soulless bourgeois drone who crowds the subway platform and lives a life of quiet desperation.
At this point, says Semmelhack, "Men have lost their ability to wear pretty things . . . If you are a man who is interested in some decoration, there are two places where you are allowed it: your tie and your footwear."6
A Little Shoe Leather
My obsession has brought me to the hushed reading room of the Library of Congress's Adams Building. Several bound copies of old English and American shoe trade journals are spread out on the table in front of me. There is the Shoe Leather and Trader Gazette from 1884, the Boot and Shoe Recorder from 1899, International Footwear Fashion from 1914.
I am trying to find the very first wingtip.
Now, when I say "the very first wingtip," I mean the earliest shoe that embodies all of the design elements found on the modern shoe of this name. This includes not only the aforementioned broguing, apparently the first design feature to be developed, but also "pinking," which is the serrated edge given to any exposed piece of leather; the semi-floral "medallion" design that's punched on the toecap; and, of course, the wing itself, usually formed from a combination of pinking and broguing.
Alas, my quest is not easy. I find no front-page article with the headline, "New Style of Man's Shoe Introduced; 'Like the Wing of a Bird!' Claims Inventor; Destined for Glory?"
What there is is a bubbling cauldron of experimentation. Here is an 1884 cycling shoe by Waterman of Bristol that features a grooved India rubber sole and distinctive broguing. Here is an 1899 Radcliffe Shoe Co. Nerve-Ease shoe with a toe medallion but no wing. There is a 1903 shoe from M.A. Smith & Sons of Philadelphia with wing and broguing but no medallion. The constituent parts of the wingtip combine and recombine like strands of DNA.
"It's very, very hard to infer influences and origins for an awful lot of things," says historian Sue Constable. "How does something just become fashionable? Now we're so used to the fashion trade telling us what's popular that fashion doesn't evolve the way it used to."
What's clear is that by the late 19th century the brogue
is often tipped by a wing and that the shoe has matured considerably since Dr. Johnson first laid eyes on it. It has a double sole and is encircled by a thick ribbon of leather -- a welt -- that's designed to keep out water. That makes it the perfect shoe to wear when hiking. It starts to pick up some of the attributes of the only people who can hike for fun: comfortably moneyed country folk. Like them, the wingtip is fashionable (but not overly ornamented), sensible, timeless.
It diversifies its role as a sports shoe: Advertisements at the turn of the century tout wingtips of various designs as ideal footwear for playing tennis and exercising at the gymnasium.7 Eventually, a shoe that is worn when participating in sports is worn when watching sports. By the 1920s and '30s so many people are wearing jaunty black-and-white or brown-and-white wingtips while attending tennis matches or horse races that the two-tone shoes become known as "spectators." In Britain they get another nickname: "corespondents," after the sneaky fellow who figures as the "other man" in a divorce case. After all, who else but a gigolo would wear such a shoe?8
History is seldom neat and tidy, and so it is impossible to precisely chart the course by which the wingtip ended up as a businessman's shoe, but it is possible to theorize: The brogue starts as a country shoe. It is matched with the suit, a country outfit. The brogue develops a winged tip. The suit comes to the city, taking the wingtip with it. The wingtip spreads as a sports shoe but is supplanted in that role as more specialized shoes are developed. It eventually becomes an office shoe, and its connection to the country is forgotten.
The Evil Cap Toe
Here is where I must make an admission: The wingtip is not the best-selling men's dress shoe in America, or even in Washington. That honor goes to something called the cap toe, a shoe with a horizontal line or seam about two inches from the toe.9
The cap toe and the wingtip are cousins, both descended from the same brogue that crawled from the Scottish bog so long ago. A cap toe often has broguing. And pinking. And a medallion.What it most emphatically does not have is the wingtip's single most inspiring feature: the wing. In its place is a flat line, the same thing that's etched across the face of an EKG machine after your heart has stopped.
But the wing, oh the wing! What imagery, what symbolism, what subconscious longing! Who among us hasn't dreamed of flying? If only, like the Roman god Mercury,10 the wings on our shoes could really carry us skyward, allowing us to slip the surly bonds of Earth and fly.11 This lofty detail is what makes a wingtip a wingtip, which the Oxford English Dictionary12 defines as a shoe "with a toe cap having a backward extending point and curving sides, suggestive of the shape of a wing."
What I love about the wingtip is not just the way it reaches for the stars, but the plasticity of its design. The wing itself can be rendered in multiple ways: from subtly arched like Hercule Poirot's mustache to deeply peaked like a pair of inverted Matterhorns. The same goes for the pinking (from rudely saw-toothed to practically nonexistent), the broguing (usually something like this: o:eek::eek::eek::eek::eek:, but sometimes this: O O O O O O, or even this: <>:<>:<>:<>:<>) and the medallions (which come in as many versions as do the beaks of finches).
They all coalesce in perfect proportion in what many consider the classic wingtip: the Florsheim Imperial. I have a pair that I purchased seven or eight years ago.13 They are what's known as long-wing bluchers.14 The long wing, also known as a full wing or full brogue, means that the broguing and pinking extend from the wing all the way around the shoe, like a high-water mark. Ron Rider, who designs custom shoes for Franco's Fine Clothiers in Richmond, calls this "the postwar wingtip. That was the official urban workforce wear . . .15 When you're designing a city shoe, that's the stereotypical model you might work off of."
And designers are still working off that ur-wingtip, tinkering with its features as those unknown wingtip inventors did.
"It's a challenge, but it's fantastic," says William Evans, designer for Britain's R.E. Tricker Ltd. "They're such classic shoes that you can't do really radical things with them."
Says Mike Rancourt, designer for Allen-Edmonds: "It's timeless . . . I can look at [other] styles that have gone out of fashion, and they've dated completely. The wingtip is just the exception. It's always in the line. You'll always see it in the shoe store."
At the Feet of Fred MacMurray
What does the wingtip mean?
"To me, it means experience," says Rusty Ortiz, manager of the Allen-Edmonds shoe store on Connecticut Avenue NW. "You're going to be in business for a long time."
To David Lee Tayman, a bankruptcy attorney in the District, wearing a polished pair of wingtips means, "You're looking to look competent and not overly cocky."
There's nothing new about this belief that the shoes -- and feet -- are powerful messengers. In his 1888 book, The Human Foot, William Beneke, who owned a Manhattan shoe factory, wrote: "People may be judged from their clothes as to their taste and means, or by their features as to their intelligence. From their shoes one may read a person's character, sometimes with great exactness."16
So powerful is the wingtip's mojo that it appears on everything from Doc Martens to baby shoes. Recently at the National Museum of American History, Priscilla Wood, associate curator of the Smithsonian's costume collection, showed me a pair of men's patent leather slip-ons, size 8 1/2,17 with decorative grosgrain ribbon, designed by Ralph Lauren in 1974. They were tuxedo shoes, a very specialized and somewhat foppish creation intended to be worn with formal dress. On each toe: a wingtip. Why did Ralph Lauren do that?
"To make the shoe look much more masculine," said Wood.
Masculine, experienced, competent, established.
Sort of like Steve Douglas, the widowed engineer played by Fred MacMurray on the 1960s sitcom "My Three Sons." The show's opening credits feature an animation of three pairs of legs, visible from the knee down. These are the aforementioned sons, and their footwear depicts the Three Ages of Man more succinctly than any riddle-spouting Sphinx.
In the middle is the youngest boy, Chip, dressed in white tennis shoes (Chuck Taylors? Keds? It's hard to tell). On the left is Robbie, the middle son, wearing penny loafers, those classic preppie casual shoes. On the right is Mike, the oldest. He is ready to adopt the mantle of adulthood and is dressed accordingly: in a pair of wingtips.
As surely as autumn follows summer, Robbie will follow Mike and Chip will follow Robbie, each quite literally walking in his older brother's footsteps.
And that is what the wingtip is: the ultimate grown-up shoe. It is a shoe for adult males, the way a suit and tie is an outfit for adult males.18 And that's why I wear both of them. I don't decry the casual dress movement because it is casual, but because it is childish, erasing as it does some of the differences between an 8-year-old boy and a 38-year-old man. A suit may be a costume, a shoe may be a prop, but aren't we all playing roles? And doesn't a fetish worn and consecrated by so many others help me play my part?
So when I wear my wingtips,19 I'm using them to send a message. And that message is: I'm a man. I'm a man who likes shoes.
John Kelly's column, "John Kelly's Washington," appears every weekday in The Post's Style section.

1. An ankh is a cross with a loop on the top. Incidentally, most ancient Egyptians went barefoot or wore sandals woven from papyrus rushes. Dozens of pairs of sandals were buried with King Tutankhamen, including some that had images of his enemies on their soles.
2. Constable is "shoe heritage officer" at the Northampton city museum. Northampton's museum has a shoe heritage officer because Northampton has a shoe heritage. The central England city has been the footwear capital of Britain since the 14th century. The industry was sufficiently developed by 1642 that the town's cobblers were able to accommodate a single order for 600 pairs of boots and 4,000 pairs of shoes. Today such well-known brands as Church's, Cheaney, R.E. Tricker and Edward Green are made in Northampton.
3. The Germans call it a "Budapester," after the Hungarian city where many brogues are made.
4. Named after Tomas Bata, a Czech who revolutionized the production of shoes. As with most fashion archives, the vast majority of the shoes in the Bata collection are women's. "Men don't tend to save their shoes," says Semmelhack. And compared with women, men "don't have the same sentimentality to their footwear." I hope in some small way this article will help address this imbalance.
5. But not a George Washington. Although the father of our country owned a queue, a sort of clip-on ponytail, he did not wear a wig.
6. The origins and symbolism of the necktie will have to wait for another day. Some scholars say the tie owes its origins to a group of Croatian mercenaries who fought on the side of the French in the 17th century. These soldiers wore scarves knotted around their necks, eliciting much admiration among Parisians, who adopted wearing scarves "à la Croat," or "in the style of the Croats." This morphed into "cravat," an early word for necktie.
7. And playing golf. I had always assumed that the prototypical golf shoe looked the way it did -- that is, like a wingtip -- because it was a parody of a dress shoe. In fact, it's the other way around. The dress wingtip is a formalized version of its more informal forebear.
8. There are other examples of an article of clothing being named for the supposed characteristics of the person who wears it. See also the sleeveless T-shirt known popularly as a "wife-beater." Incidentally, the Prince of Wales, Edward VIII, who traded in the throne for a divorced American, was said to be partial to spectators.
9. George W. Bush favors cap-toed dress shoes. At least that's what he wore at his second inauguration.
10. Mercury was the god of commerce; interesting, given that wingtips are often worn by businessmen.
11. I'm paraphrasing John Gillespie Magee Jr.'s famous poem "High Flight." See also these lyrics from the Steve Miller Band's "Fly Like an Eagle": "I want to fly like an eagle / To the sea / Fly like an eagle / Let my spirit carry me / I want to fly like an eagle / Till I'm free / Oh, lord, through the revolution / Feed the babies / Who don't have enough to eat / Shoe the children / With no shoes on their feet." [Emphasis added]
12. The Oxford English Dictionary is named for the book's publisher: the Oxford University Press, not for the type of shoe known as an "oxford." An oxford is a low-cut, laced shoe. It may be of either a balmoral or blucher design, more on which later. Unfortunately, no one really knows how the oxford shoe got its name.
13. Mine were made in the United States. In 2002 the assets of a bankrupt Florsheim were bought by a shoe conglomerate, the Weyco Group, and Florsheim shoes are now made overseas. Incidentally, the Florsheim Imperial should not be confused with the Florsheim Crown Imperial. The Crown Imperial used a type of hide known as shell cordovan. Though cordovan has come to mean a reddish color, shell cordovan is leather made from the hindquarters of a horse. The word "cordovan" itself comes from Cordoba, the Spanish city renowned since the 8th century for its leather tanning. Alden and Allen-Edmonds are the only U.S. companies making shell cordovan shoes in quantity. They both use horsehide tanned by the Chicago firm Horween, the company that also supplies leather for official NFL footballs. (That's right: The ol' pigskin is made from cow skin.)
14. In a blucher, two leather flaps are laced together loosely over the tongue. The style is named for Gebhard Leberecht von Blucher, a Prussian field marshal who fought against Napoleon at the Battle of Waterloo. He procured for the troops under his command shoes with flaps that laced over the tongue. (Before then soldiers were likely to wear boots without laces.) Footwear history was made in another way at Waterloo: Britain's Lord Wellington was dressed in a stylish high boot that came to be associated with him. (It is as if today men wore "Schwarzkopfs.") Wingtips also come in the tighter-fitting and more streamlined balmoral style, whose name comes from Queen Victoria's Scottish estate.
15. When Ron Rider says "official," he, of course, means "unofficial." I can find no evidence that men were required to wear wingtips as part of their terms of employment. A common belief that wingtips were a mandatory wardrobe element for FBI agents is apocryphal. I have a letter dated January 20, 2005, from Ben Fulton of the Society of Former Special Agents of the Federal Bureau of Investigation Inc. that says: "Regarding your inquiry, there is NO truth to the claim that FBI officials were required to wear wingtip shoes . . . Of course, wingtip shoes were popular and many Agents wore them, but there was no such regulation, official or unofficial. You would be wrong and amiss to include such a claim in your story."
16. Beneke's book is a powerful argument for the notion that the soles are the window to the soul. He writes: "Good judges of such matters are well aware that large feet, as a rule, indicate good business ability, integrity, perseverance and other good qualities. Give me a man with big feet to deal with. A large firm foot may indeed serve as a recommendation."
17. This is, coincidentally, the size shoe that I wear. The average American man has a shoe size of 10. The average American woman's shoe size is 8.
18. For the record, I've never seen my father, now 66, in a pair of wingtips. He was an Air Force pilot, and I associate his adulthood with flight suits and flying boots, a look I would have a tough time pulling off.
19. And I don't wear them every day. Experts recommend letting shoes rest for two or three days between wearings
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