The “Panama Hat” of Montecristi, Ecuador–one of the masculine luxuries of the world

Montecristi Panama HatPanama Hats

What came to be called “Chinese Checkers” in 1928 was actually invented in Germany in 1892 and is not a form of checkers. And French fries, it is believed, originated in Belgium. But when it comes to misnomers, the Panama hat takes the crown, for the hats are actually made in Ecuador. And while, understandably and rightfully, Ecuadorians themselves never refer to the hats as “Panama hats,” but instead as “sombreros de paja toquilla,” the rest of the civilized world calls them Panama hats, oftentimes having no knowledge of the true origin of the hats.

The History of the Panama Hat
In 1526, when Spanish conquistador Francisco Pizarro arrived in what is today Ecuador, he encountered the inhabitants of the coastal areas wearing almost-brimless headwear made of woven straw. And those 16th-century straw hats apparently had ancient origins, for ceramic figures from the region dating back to about 4000 B.C.E. depict persons wearing headwear similar to that worn by the Ecuadorians encountered by Pizarro. The Ecuadorian straw hats also resembled the European “toque,” a diminutive hat with a small brim, fashionable during the 16th century. Consequently, the Europeans called the straw used to make the local hats “paja toquilla,” presumably after “toque.”

Beginning as early as the middle of the 1500s, hat-weaving had emerged as a cottage industry all along the Ecuadorian coastline, with hat-weaving and hat-wearing becoming more popular in the 17th and 18th centuries. Even then, however, the hats of highest quality came from what is today the Province of Manabi. And in Manabi two towns, Montecristi and Jipijaba, emerged as the leaders of the blossoming hat-weaving industry, both towns gaining a reputation for producing the absolute finest hats.


How a Hat Made in Ecuador Came to be Called “Panama Hat”
In 1835 Manuel Alfaro migrated from Spain to Ecuador, settling in Montecristi and establishing himself in the local hat industry. With the intention of exporting the hats, Alfaro organized the various hat artisans into a viable production system. He sent his hats to the port cities of Guayaquil and Manta, bound for Panama, a crossroads of the Americas and gateway for the East and West. Alfaro also established a trading company in Panama, dealing in hats, cocoa, and pearls. And when the California Gold Rush hit in 1849, the hat of choice for providing protection from the sun while panning gold was the Ecuador-made straw hat.

Also significantly contributing to the misnomer is the fact that during the construction of the Panama Canal (1881-1914), the 48-mile manmade waterway that cuts across the Isthmus of Panama to connect the Atlantic and Pacific Oceans, many of the laborers donned Panama hats since the lightweight hat provided excellent protection from the sun. But one of the greatest publicity boosts for the now-classic hat occurs in 1906 when a photo of American president Theodore Roosevelt sitting at the controls of a steam shovel during his three-day inspection tour of the construction of the canal was published in seemingly countless newspapers and magazines the world over. The early 20th-century equivalent of “going viral,” the photo helped established the hat as a fashion statement as well as to indelibly associate the hat with Panama.

By 1850, Americans had developed a taste for the Ecuadorian hats—not carrying a label of origin—that were widely sold in Panama. Thus, is was only a matter of time before the hats became known as “Panama hats,” Americans purchasing 220,000 per year in the middle of the 19th century.

Manuel’s son Eloy Alfaro (1842-1912) joined the family enterprise and expanded the company’s prominence and channels of distribution. Eloy would go on to become the first-elected president of Ecuador, serving two terms: 1895-1901 and 1906-1911.


The Making of the Panama Hat
Approximately 20 steps and an equal number of specialists are required to produce one Panama hat from start to finish. The end result, however, is one of the world’s true masculine luxuries: There is a certain, particular, undeniable je ne sais quoi achieved when a gentleman effortlessly wears a Panama hat.

The Paja Toquilla palm-like plant that produces the fine straw from which all genuine Panama hats are made is native to South America. And when gathering the raw material to construct Panama hats, only the best frond-stalks from the best plants are selected. (The stalks are cut in a special way so as to ensure the regrowth of the plant.)

After the stalks are selected, they are beaten on the floor, causing the tubular-shaped stalks, each about four feet long, to transform into long strands or streamers. The tip of a needle is then used to further separate the strands into narrower strips. The beaten stalks are then rapidly boiled then hung out to dry in the sun.

Once thoroughly dried, the strands are placed into an oven to be smoke-bleached, using Sulphur, for approximately 24 hours. After the smoking and bleaching, the strands transform into Paja Toquilla straw.

Once removed from the smoking-oven, the best straw is hand-selected for the finest hats, with the lesser-quality straw set aside for lower-quality hats. The straw is evenly cut; then each strand, using the tip of a thumbnail, is further divided into thinner strands. The thinner the straw, the finer the hat.

The prepared straw is then given to an “armador,” who starts weaving the hat with about 12-18 strands of straw. He or she makes the very center of the “plantilla,” the middle-center of the top of the hat’s crown. While some “armadores” use wooden hat blocks when weaving the “armado,” others weave it free-hand.

After the “armador” has done his or her work, the hat then goes to a “weaver,” the person who does the majority of the work, weaving the crown and brim of the hat. Depending on the fineness of the straw, a weaver may take up to several months to complete a single hat.

Once the weaver has woven the crown and brim to the desired size, the hat is handed over to a “rematador,” who weaves the end of the straws back into the brim of the hat, thereby creating an edge that does not unravel. Once that task has been completed, the hat is regarded as “remate.”

Once “remate,” the hat passes along to an “ajustador,” whose job it is to tighten all the straws around the “remate” edge of the brim.

Thereafter, the hat undergoes its first trimming—and the straw extending beyond the “remate” and “adjustado” brim is clipped off with scissors, thereby facilitating the remaining steps in the hat-making process.

Next comes the “lavado” process, where the hat is washed in soap and water, with the aid of a scrubbing-brush. After all, by this point, the hat has been intimately handled by numerous craftsmen, each working with his bare hands.

After a thorough washing, the hat is allowed to air-dry for 24 hours before it is smoke-bleached in an oven, a process which takes a full day. Once removed from the smoke-bleaching oven, the hat is again trimmed.

“Apaliado” describes the process whereby stacks of about six hats are beaten by hand with the use of a wooden mallet, Sulphur sprinkled onto each hat as it is being stacked for the collective pounding. The purpose of the beating is to make the hat more pliable, improving its overall appearance and feel in the process. Special care must be taken to use the right amount of force, for a hat beaten too hard can be destroyed.

Once “apaliado,” the next step is the “planchado,” where several things occur: The hat is assigned a size based on its woven size; the hat is fit onto a wooden hat block; a flat iron is used to iron-out creases in the hat and to give the hat’s brim a good balance; and a break line is created so as to distinguish the brim from the crown. An ironing cloth is used so as to prevent the straw from coming into direct contact with the hot iron (typically an iron, the heating source of which is hot coals that are deposited into the belly of the iron via its “mouth”).

With the aid of a razorblade, the hat is then given a careful, meticulous, final trim.

Hats are then placed onto wooden hat blocks called “shaping-blocks” so that the milliner can give each hat its final shape (with pinched or creased crowns, etc.) (Whereas the finest hats obtain their final shape by hand, hats of a lesser quality are machine-pressed into their final shape).

The finest Panama hats are sold in wooden boxes of balsa—but so are counterfeits, so caveat emptor!

The Grading of Panama Hats
Today, there are two centers of Panama hat production in Ecuador: The city of Montecristi, and the city of Cuenca, the former situated on the coastline, while the latter is located in the foothills of the Andes Mountains. Though Cuenca produces more hats, the finest hats come from Montecristi, so much so that many Cuenca-made hats are surreptitiously marketed as of Montecristi origin to unsuspecting customers and to meet international demand. Each year there are more Cuenca-made hats sold as “Montecristi” hats than there are Montecristi hats made for sale as such. (The best Cuenca hats come from the town of Biblián, just outside Cuenca proper. Weaving-wise, they rival the hats of Montecristi and Jipijapa. Color- and texture-wise, however, they are not as refined as their coastal counterparts).

Most Montecristi hats are today woven in towns and villages—such as Pile and Pampas—that are situated close to Montecristi. But many of the finishing steps of the production of the hats still take place in Montecristi proper. (See above, “The Making of the Panama Hat”).

In 1836, in response to the increasing popularity of Panama hats, the city of Cuenca, situated in the Province of Azuay, entered the hat industry. Within a few years, Cuenca workshops were thriving, training all who were willing and able to learn the trade. In 1845 Don Bartolome Serrano of Cuenca hired master weavers from the Province of Maniba (in which the city of Montecristi is situated) and went about the business of upgrading then streamlining Cuenca’s production of Panama hats.

But today, an unhealthy rivalry between Montecristi and Cuenca, fueled partly by outside forces demanding the best Panama hats, has resulted in the degradation of the esteemed reputation of one of the true masculine luxuries: an extra fine Montecristi, Ecuador, Panama hat. Mislabeling, false declarations, unwitting buyers, greed, etc., have all resulted in a misnomer of a misnomer.

In order to protect the integrity of the authentic Montecristi Panama hat, The Montecristi Foundation has taken the necessary steps to establish the equivalent of a protected and guaranteed Denomination of Origin that would promulgate manufacturing-standards for the hats; specify the geographical boundaries within which hats labeled and or marketed as “Montecristi” must be made; establish a recognizable logo of authenticity that should be used by all qualified manufacturers; etc.

In the meantime, there is no universally accepted grading-system for Panama hats. Terms such as “grade 10” to describe the highest grade hat or “Fino Fino” or “Super Fino” to describe top-quality hats from Montecristi mean different things to different hatmakers. And such terms are also deliberately misused by unscrupulous vendors to mislead buyers. The moral of the story, therefore, is that a gentleman desiring top-quality Panama hats should purchase hats made in Montecristi or Jipijapa and sold by the most reputable manufacturers. Brent Black’s The Panama Hat Company of the Pacific ( ) is one of the world’s foremost purveyors of high-quality, authentic Panama hats of Montecristi, Ecuador. The company’s website offers a wealth of information, including how to properly measure one’s head when ordering a hat; how to determine the quality of hats; how to care for Panama hats; etc.

Traditionally, one way to gauge the quality of a hat is to count the number of rings in the center of the crown. The general rule is that when it comes to rings, more is more, not less. But that method of determining hat quality is not foolproof. To the extent that it is employed, however, a hat with 10-12 rings—perhaps best determined by holding the hat up to a light, observing from the inside of the hat—is considered good.

A more reliable way to judge a quality hat is to tediously and painstakingly count the number of weaves in a vertical inch and then the number of weaves in the corresponding horizontal inch, thereafter multiplying the two numbers. A hat with, for example, 30 horizontal weaves per inch and 28 vertical weaves per inch (Rarely do the vertical and horizontal weaves number the same.) would have a weaves-per-inch count of 840. A hat with a weave-per-inch count of 900 would be exceedingly rare. (There was once a hat woven with straw so fine that it was finer than fabric. Because the hat was so labor-intensive, it has disappeared, the weavers who wove such hats long dead).

But there is more to an exquisite Panama hat than number of weaves—somewhat the adage, “It’s not size; it’s how you use it….” The quality of the weave is also or paramount importance. Most lay persons can see the difference between a poorly woven hat and an exquisitely woven one. The difference between “very good” and “exquisite,” however, is a much more subtle distinction. Uniformity of color is also more desirable than non-uniformity. At the end of the day, though, the best Panama hats are handmade of natural materials. And as such, every hat will have some minor, even if almost imperceptible, “imperfections” that in many ways add to the charm and uniqueness of the hat. An undyed leather sweatband is preferred.


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The Seven-Fold Tie–the most luxurious of all men’s ties

Exquisite Ties
It is oftentimes said that a gentleman should never compromise on the quality of his shoes, his belt, or his necktie, for they are barometers of taste. A tie is a deceptively simple accessory: The making of a standard long-tie involves approximately 25 steps. A good tie should be made by hand—not by machine—of an exquisite shell (outer) fabric and an excellent lining and interlining. But the crème de la crème of long-ties is the “self-tip, seven-fold tie,” made by hand of a luxurious fabric, with the shell fabric being folded inward upon itself as the tie is being shaped, thereby eliminating the need for any interlining or lining of other fabrics. Consequently, the seven-fold tie consumes more than twice the amount of the shell fabric than other handmade ties, and, as a result, typically costs more than twice as much. But for the connoisseur, the seven-fold tie, with its special “finishes” such as “self-tips,” a “self-loop,” hand-crocheted bar tacks, and a hand-tacked label reward its wearer tenfold. And immediately upon beholding such a tie, one senses its special attributes. As is said in the trade, a seven-fold tie possesses a superior “hand.”

The History of Tiepins and Tie Clips

The Tiepin

The tiepin ( “tie pin,” “stickpin,” “stick pin”) dates from the early 1800s and was used to secure the folds of a cravat. By the 1870s, when long-ties emerged onto the fashion scene and men’s shirts were being designed with button-up fronts, tiepins were used to decoratively secure the tie to the placket of the shirt, preventing the tie from blowing about in windy environs such as onboard yachts and at outdoor sporting and social events.

The Tie Clip

By the 1920s, however, when long-ties of very delicate silk fabrics became popular, tiepins were succeeded by tie clips (“tie bar,” “tie slide,” “tie clasp”). Tiepins, because of their design, pierce the fabric of the tie in the process of securing the tie.  And with repeated use, they may cause damage to a delicate tie.  A tie clip, on the other hand, clips the long-tie to the placket of the shirt without penetrating or damaging the tie in any way. Both would remain a part of menswear accessories until the end of the 1960s, when both fell out of fashion favor—partly because ties went somewhat out of fashion in the ’70s with mod fashion of the Hippie Movement and the leisure suits of the disco era. But since the beginning of the 21st century, tie claps (but not tiepins) have made a triumphant return.

Like all masculine jewelry, less is more. A simple, understated tie clip of silver, gold, or some other precious metal is recommended. A tie clip remains one of the few items of jewelry permissible while in  military dress.


The Difference Between Oxfords And Derbys–two of the most classic styles of men’s shoes

Oxfords and Derbys

Oxfords (also called “Balmorals” after the monarch of Great Britain’s Balmoral Castle in Scotland) have their origins in Scotland and Ireland. The stylistic origin of the now-classic shoe is the “Oxonian,” an 18th-century half-boot with two side slits that became popular with Oxford University students around the year 1800. Eventually, the side-slit boots were designed with side-laces. But as the students rebelled against knee-high and ankle-high boots, the boots were cut down, becoming shoes with their laces at the instep.

To the untrained eye, oxfords and derbys (also called “blüchers”) are one in the same. But the fundamental difference between oxfords and derbys (despite variations in terminology from one region to another) is that the lace eyelet tabs of the oxford are stitched under the vamp (a construction commonly referred to as “closed lacing”), while the lace eyelet tabs of the derby overlap the vamp (a construction commonly referred to as “open lacing”). Because of the sleeker, more “contained” construction of the oxford, it is regarded as the more formal of the two classic styles. Both styles, however, have remained immensely popular for over 200 years.

The History of Boots


The History of Boots

For many men, walking into the shoe department of a major store can be daunting; there are oftentimes so many styles from which to choose. But to observe shoes carefully is to realize that most footwear  falls into a handful of categories:  sandals/slippers, moccasins, boots, court shoes (tuxedo pumps), oxfords, and sneakers. And for the gentleman who enjoys a comprehensive lifestyle, having a pair of shoes from each category is essential.

Man has worn shoes from time immemorial; the oldest known footwear—a pair of sandals made of woven sagebrush bark and found in Fort Rock Cave in the state of Oregon—is believed to be at least 10,000 years old. The oldest known leather shoe was found in a cave in Armenia and dates from around 3500 B.C.E.  Ötzi The Iceman, who lived around 3300 B.C.E, was wearing footwear constructed of bearskin and deer hide. It is believed that shoes were first created to protect the foot. But over time, its purpose became twofold:  to protect and decorate.


As with coats, lifestyle is a major factor in determining what type boots a man will wear. And there are boots designed for just about every type of lifestyle:   A gentleman-farmer has his Wellingtons (also called “gumboots”); a fly-fisherman has his waders; a Tom of Finland enthusiast has his biker boots; a Texas oilman has his western boots; a gentleman of the dressage has his riding boots;  and for yet other gentlemen, the only boot worth wearing is a Timberland….

The earliest boots consisted of separate parts:  soles, uppers, and leggings. But around 1000 B.C.E., the various components were joined to form a single unit. One of the earliest examples of an integrated boot dates from around 900 B.C.E. It is a pair of terracotta boots, presumably a replica of what she would have worn in life, found at the cremation burial site of an ancient woman and is housed at the Ancient Angora Museum in Athens. Some 2,000 years later, between the 13th and 16th centuries, a type of soft leather boots worn by the nomads of eastern Asia was introduced to China, India, and Russia by Mongol invaders. By the 18th century, Hessian (German) soldiers, contracted by the British to fight against the colonists in the American Revolutionary War, were wearing knee-high boots.

Men’s Overcoats (in general) and Trenchcoats (in particular)

Men’s Coats

To a large extent, a man’s outerwear needs are determined by climate and his lifestyle. For a Caribbean gentleman, outerwear may amount to a good umbrella and, perhaps, a sturdy raincoat. But for a Canadian gentleman, a down-filled or fur-lined coat might be a necessity. Whether a man typically uses private or public transportation also influences the type of outerwear he must select:  A gentleman who must wait at bus stops and stand on subway platforms in cold weather will have different outerwear needs than a man who dashes about town and country (within the speed limit, of course!) in a private vehicle.

Overcoats (Top Coats, Greatcoats)

From times Biblical, coats have come in many colors. But today, they also come in many shapes and sizes to meet the varied needs of modern man. There are, for example, ponchos and parkas; trucker jackets and duffel coats; pea coats and the slightly longer bridge coat; polo coats and trench coats, etc., all designed for providing warmth, protection, and/or fashion.  But one thing is for certain:  Whenever a man wears a coat with his suit or with formal wear, that coat should be an overcoat (also called a “topcoat” or a “greatcoat,” depending on the weight of its fabric, the top coat being the lighter). With formal wear, a gentleman for whom money is no object might wear a black topcoat of vicuña or cashmere, perhaps with a collar/lapel of sable. But for everyday business wear, a number of fabrics—primarily wools—are appropriate. (In the 1920s and up until the 1940s and ’50s, some men of means would don fur coats; but by the 1990s, the practice—independent of the consciousness raised by animal rights activists—would come to be regarded as distastefully ostentatious. Today, a gentleman who wears fur would wear it as the lining of a coat of exquisite fabric, with, perhaps, only the collar/lapels of exposed fur; or he may wear a fabric coat with a collar/lapel of fur. But the days of gentlemen in full fur coats are gone—at least for the foreseeable future).

Whether a coat is single- or double-breasted, styled with peaked or notched lapels, or designed with raglan or set-in sleeves, for example, is a matter of personal taste and the degree of formalness desired. (A shawl collar or peaked lapel is more formal than a notched lapel, for example; and set-in sleeves are more formal—even if not more comfortable—than raglan sleeves).  But what is critical is that a gentleman procure his overcoat from a reputable outerwear establishment, which will likely only offer well-made garments of good-quality fabrics.

The best way to ensure the proper fit of an overcoat is to try on the coat over a properly fitting jacket since overcoats are designed and constructed to be worn over jackets.  A man who wears a 42L jacket, for example, would wear a 42L overcoat. The overcoat’s shoulders, therefore, would extend slightly beyond those of the jacket, and the sleeve length of the coat would extend beyond that of jacket by about one inch.


For a gentleman who must wear a suit or jacket in cold, rainy weather, a trenchcoat is a wardrobe essential. (In such weather, a gentleman in formal attire would not wear a trenchcoat over his tuxedo or tailcoat.  Instead, he would wear his black overcoat and protect himself from the elements with a black umbrella).   A trenchcoat is primarily a raincoat, generally constructed with a removable insulated lining. Ranging in length from mid-calf to above-the-knee, the traditional color is khaki, but olive drab is also popular. Waterproofed cotton gabardine, poplin, or drill are the traditional fabrics of choice.

Whether the trenchcoat (also “trench coat”) was first designed in the 1850s by John Emary of Aquascutum or in 1901 by Thomas Burberry is likely to remain a matter for debate for the foreseeable future. What is known for sure, however, is that in World War I, the coat served as a welcomed alternative to the traditional, heavy serge greatcoats that had proven too cumbersome in the trenches of previous wars.


The History of Men’s Belts–(and everything else a gentleman should know about them)


Belt loops on trousers, as incredulous as it may seem to a gentleman of the 21st century, is an invention of the early 1900s. [A 1908 Macy’s catalogue offers men’s trousers with loops]:  It was in 1922 that Levi Strauss & Co., got the idea to put loops on its jeans so as to accommodate belts since many of the company’s customers wanted more flexibility and security than could be obtained with traditional suspenders.  Before the early 1900s—from as early as the Bronze Age—belts, from cording to fabric sashes to leather, had been worn by men for aesthetic reasons or to create the illusion of the idealized male physique of broad shoulders, salient chest, and a small waist.  And throughout human history, belts have been worn with military dress to enhance the male physique and to secure and/or transport weaponry. But beginning in the 1920s, with the rising popularity of pants being constructed with belt loops, belts began being worn for the purpose of keeping up pants.

The most basic form of belt is a rope, cord, or fabric sash, usually worn taut around the waist. The drawstring is also a rudimentary form of belting. But the finest belts are:  handcrafted and made of exotic skins or exquisite leather; lined with latigo or some other durable leather; interlined to create contour; finely stitched around the perimeter; finished with beveled edges; appointed with buckles and other hardware of solid metal, sometimes precious; and finished with hand-rubbed edges and dyed buckle holes, for example. Good belts come in a wide range of prices:  from very reasonable—especially when brand-name and designer belts are discounted—to pricing that is prohibitively expensive (but with justification) for the average man.

Color and Texture

When dressed professionally or formally, the color and finish of a gentleman’s belt should match that of his shoes. Most men, then, find it absolutely essential to own at least two dress belts:  one black and one brown. But since all blacks and browns are not created equal, it is best to wear or carry one’s shoes to the belt store when purchasing a belt to be worn with those shoes. A flat-finished black belt, for example, would not be a proper complement to black patent leather shoes. (In the case of the new “American black tie,” where a cummerbund is not worn and therefore cannot cover the belt, a gentleman—especially one of modest height or substantial girth—who wears black patent leather pumps may opt to wear a more understated black belt [if the trousers require a belt] so as to create an uninterrupted visual flow between his jacket and pants). Likewise, a pair of shoes of mahogany brown might not match well with a belt of mocha brown. It is also important that the width of the belt fits typical belt loops. And for a man with only two belts, it is advisable that his belt buckles be simple and classic—preferably made of brass or chrome. The rules are slightly different for casual dress. The general rule is to match casual belts, such as multi-colored web belts with box-frame buckles, with the color scheme of the overall outfit, not necessarily with the shoes. A gentleman wearing a pair of white Nike sneakers would not, for example, be expected to wear a white belt. Instead, he should choose a belt that complements his outfit in general.


Conventional wisdom is that a man’s belt-size should be two sizes larger than his pants’ waist-size. So, for example, a man who wears 32-inch waist pants should purchase a size 34 belt. Most belts tend to have five buckle-hole options. The objective should be to purchase a belt that fits when the buckle is secured into the third, or middle, hole. And as a gentleman’s weight fluctuates, he should select the hole on either side of the middle hole. Whenever his waist-size is such that he must select the first or last hole, that is an indication that his belt is either too large or too small.  The waist-rise of a pair of pants may also affect the size belt to be worn with those pants. A pair of pants that fits onto one’s upper-hip will require a longer belt than a pair of pants that fits onto one’s true waistline. A man who wears “size 32-inch waist” low-rise pants would typically need a size 36 belt since a man’s “lower waist/upper hip” is generally about two inches larger than his “true waist.”


Belts may be loosely coiled and set atop a flat surface such as a wardrobe shelf or tabletop.  Belts with openwork buckles may also be hung from a clothing hanger by passing the open space of the buckle through the hook portion of the hanger and allowing the belt to hang freely. Never, however, should a belt be halved and hung over the crossbar of a clothing hanger, for such a storage method will eventually compromise the shape of the belt.


Like shoes, belts should be allowed to “rest” between wearings. It is best to wear a belt every other day, rather than every day, allowing the belt to air-dry and regain its shape.  Belts with buckles made of metals that tarnish should be regularly polished.



The History of the T-shirt–one of the greatest sartorial classics of all time

The T-shirt

The T-shirt derives its name from its shape: When laid out flat, sleeves perpendicular to torso, the garment forms the letter “T.” (So technically, there is no such thing as a “sleeveless T-shirt,” a term oftentimes misused to describe the “athletic shirt”). (See “A-shirt” below).

Along with jeans, the T-shirt is often credited with being the most popular garment of the second half of the 20th century and now the 21st, serving in every capacity from undergarment to work shirt to walking billboard to pajama top to regular shirt. Almost every man on the planet has at least one T-shirt in his wardrobe. And T-shirts have become the events memorabile and tourist souvenir item of choice—so much so that there is the saying, “Been there, done that, got that T-shirt.” T-shirts are generally inexpensive, low-maintenance, comfortable, and forgiving in their fit. So what’s not to like about them?

If classic is defined as that which has stood the test of time, then the T-shirt is one of the great sartorial classics of all time. The T-shirt made its way onto the fashion scene sometime between the Spanish-American War in 1898 and just before World War I in 1913 when the US Navy began issuing them as undergarments. But the submariners, who typically had to work in close, hot confines, would wear the T-shirts as an outer garment in order to receive some reprieve from the heat. After the war, the former military men continued wearing T-shirts—as shirts—in their civilian life. By 1920 the term “T-shirt” had been listed as an official American-English word in the Merriam Webster Dictionary. And the basic design of the T-shirt—with its jersey-knit cotton fabric; collarless, crew neckline; short sleeves; and tubular torso—has remained virtually unchanged ever since. By the 1940s, the T-shirt had come to be regarded as the unofficial “uniform” of laborers: bakers, miners, farmers, mechanics. The former undergarment had emerged as standard outerwear. But it was in the 1950s, when Marlon Brando in A Streetcar Named Desire and James Dean in Rebel Without A Cause nonchalantly wore T-shirts as regular shirts, that T-shirts became a must-have for teenaged boys. The T-shirt allowed young men, inspired by Brando and Dean, to unabashedly display gender—in an erotic way that had previously been regarded as socially forbidden.

Using the T-shirt as a means of advertising was also born in the 1950s, starting when the Miami-based company Tropix Tops obtained the exclusive rights to print images of Mickey Mouse and other Disney characters on T-shirts to promote the Disney brand. The company also started printing the names of Florida resorts on T-shirts, marketing the State as a tourist destination in the process. Almost immediately thereafter, rock bands were using T-shirts to promote their new releases. By 1967, T-shirts were being used as walking, breathing, interactive placards for social and political commentary as well as serving as a canvas for pop art. And because the classic T-shirt is unisex, women began wearing them in the ’60s. At 1969’s Woodstock, it was the tie-dye T-shirt that embodied the ethos of the historic gathering: young, carefree, and colorful.

But if bold tie-dye T-shirts epitomized the anti-establishment, mod dress of the Hippie Movement of the ’60s and ’70s, then it was the pastel-colored T-shirts worn by Miami Vice star Don Johnson that would give rise to the concept of “casual-chic” in the 1980s. Johnson effortlessly (or so it seemed) paired T-shirts with expensive designer suits; and overnight, like Brando and Dean before him, redefined American fashion. And the world followed suit—so much so that decades later, Johnson’s once-iconoclastic look has become iconic.