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Damned Dapper: The Origins Of The Go-To-Hell Look

Charlottesville, Virginia

June 3, 2020

I grew up wearing a school uniform from the fourth grade through high school. Gray pants, white shirt, school tie, gray blazer with gold piping (and then a blue blazer in high school). Occasionally we would be given the "privilege" on a Friday of wearing a different pair of pants than our standard gray flannel. All hell would break loose. I like to think my affinity for GTH pants therefore came to me almost naturally. 🤪

I borrowed the following article from Rake magazine.


Thomas Watson Jr. was president of IBM during the years when it was a punchline for sartorial conformity. Throughout the ’50s and ’60s, gray suits for employees were standard, white shirts required.

It may seem an odd non sequitur, then, that Watson once ordered a custom sport coat whimsically embroidered with dozens of little skiers, to wear during cocktail hour at the lodge after a long day on the slopes.

Since the time of Martin Luther, the Protestant nations of the Western world have been known for a sober palette compared to the scarlet and purple of their Catholic neighbors. Perhaps this repressed sense of color ironically accounts for the riotous display of blinding pastels that characterize the preppy look of the WASP, or White Anglo Saxon Protestant, a term popularized in 1964 by sociologist E. Digby Baltzell to describe the small caste of elites that ran American business and politics.

While WASPs have largely lost their power stranglehold on American society, their influence on the world of fashion is stronger than ever. And despite their notorious character flaws (bigotry, emotional impotence, fondness for peanut butter), they’ve long led America with sterling examples of virtue and self-sacrifice.

And for that they have as good a chance for getting into heaven as anybody else — unless, of course, St. Peter guards the “pearly gates” like a nightclub bouncer enforcing a dress code. In that case, WASPs will surely have their trousers damned to the netherworld.


Tom Wolfe may seem an odd springboard for a story about color. But while the dandy author’s wardrobe may be all white, his prose is pure purple. He’s also a keen sartorial observer, and in 1976, in an article for Esquire entitled “Mauve Gloves & Madmen, Clutter & Vine,” Wolfe uses the catchy phrase “go to hell” to describe the garish pants worn by elite Bostonians vacationing on the island retreat of Martha’s Vineyard. The phrase continues to enjoy limited usage, and the passage that birthed it is worth quoting in full:

[Bostonians on Martha’s Vineyard] had on their own tribal colors. The jackets were mostly navy blazers, and the ties were mostly striped ties or ties with little jacquard emblems on them, but the pants had a go-to-hell air: checks and plaids of the loudest possible sort, madras plaids, yellow-on-orange windowpane checks, crazy-quilt plaids, giant houndstooth checks, or else they were a solid airmail red or taxi yellow or some other implausible go-to-hell color. They finished that off with loafers and white crew socks or no socks at all. The pants were their note of Haitian abandon… at the same time the jackets and ties showed they had not forgotten for a moment where the power came from.


The social history of clothing is an elusive topic, forcing the writer into the anthropological role of outside observer, removed in both space and time, as he attempts to chronicle the customs of a closed caste. Nowhere is this more apparent than in charting the dress of America’s Protestant Establishment in the years before preppy style became a mainstream commodity.

Color was present in the male wardrobe long before the dour Victorian era and its Great Masculine Renunciation, and color has reappeared in various guises ever since, perhaps most elegantly in the Palm Beach look of the 1930s, as captured in Esquire and Apparel Arts illustrations. But the particular use of color as expressed by the WASP establishment seems to have originated, or at least been codified, in the postwar heyday of the Ivy League Look, emanating from a combination of resorts, country clubs and college campuses up and down the eastern seaboard.

The summer 1953 issue of Gentry, a short-lived menswear magazine with an editorial policy as snobbish as its name implies, credits Palm Beach, the Florida resort town where Eastern Elites have long sought refuge from cold winters, with popularizing the madras blazer the previous winter season. In 1955, LIFE magazine reported on a “radical new line” at Brooks Brothers consisting of red, green and yellow blazers and trousers in 13 different colors. A company spokesman called it an entirely new category of clothing, to go along with business, formal, sport and summer wear.

And in 1963,  just six months before President John F. Kennedy’s assassination, Sports Illustrated ran “A Cool Wave of Color,”  declaring that the president golfs in lemon yellow and sails in bright red. The article continues:

At country cocktail parties for a couple of summers past there have been occasional brave red and green jackets sprinkled among the old reliable blazers and madras jackets. Pro golfers— who helped start it all— have even taken to black and white and gray to distinguish themselves from the brightly clad spectators in the gallery.

For Ethan Huber, owner of O’Connells, a traditional menswear store in upstate New York founded by his father in 1959, friendly competition helped popularize the use of color in the male wardrobe. Huber recalls his father spinning tales of local country clubs whose members would engage in a kind of sartorial one-upmanship to see who could don the most audacious hue of trousers. Customers would then come in asking for cords or chinos in ever more outlandish shades of the spectrum, and the elements of the style were set. “You still have an old generation that does this because they’ve always done it,” says Huber. “They’re guys aged 60-80 who buy a lipstick-pink shetland sweater or orange corduroys and wear them to the hockey game because that’s what they’ve done all their lives.”

But that’s a small portion of O’Connells’ clientele: “Do people actually buy those?” customers unfamiliar with the go-to-hell look will ask. “I may have 1,000 trousers in any given size, 100 of which are really fun,” adds Huber, “but 99 percent of people would never wear them.”

The most iconic colored trouser is the only one that bears a trademark: Nantucket Reds, made by Murray’s Toggery Shop, founded in 1945 on Massachusetts’ Nantucket Island, another offshore playground of the Eastern Elite. After break-in, the cotton canvas pants take on a special shade of faded red typically described as “lobster” and “tomato soup.” When paired with a navy blazer, says John Murray, son of the founder, “It’s a classic New England look.”

Indeed, in certain circles, garish pants are practically a form of fraternal initiation. Author and custom clothier Alan Flusser calls wearing go-to-hell colors “a brahmin kind of indoctrination.” For Flusser, who attended the Ivy League’s University of Pennsylvania, the origins of WASP leisurewear can be traced back to the advent of sportswear in the 1920s. “Part of the evolution of sportswear was colors that you didn’t wear in town,” he says. “And when you have money and spend time in sunny places, you begin to see color.”

Like the white flannels of the English gentleman, colorful sportswear signals the wearer is at play, not work. Easily soiled, the clothing is thus impractical, making it a symbol of both conspicuous consumption and conspicuous leisure. “Navy blue aside,” notes Paul Fussell in “Class,” his 1983 classic on the American status system, “colors are classier the more pastel or faded.”

“You wouldn’t have someone not from money walking around in clothing that would draw a lot of attention to himself,” explains Flusser. “Up to the ’60s it was always a brahmin, upper-class thing, because they could wear it and not be laughed at.” For Flusser, the postwar starting point of the look is Brooks Brothers’ celebrated pink oxford-cloth buttondown. “Pink symbolizes this whole subject matter,” he says. “Imagine a guy wearing a pink shirt: If people didn’t understand what that was about, you had to be prepared to be laughed at.

“When my brother was at Harvard,” Flusser continues, “the kids were wearing blazers and red or yellow pants and would always use color in some sort of interesting way. There was a sense of who could wear the most outrageous tattersall vest. But being able to wear that kind of clothing comes from a certain lineage where you felt, ‘This is what we do, and if people don’t understand it, they don’t understand it.’”

Flusser recalls a girl who refused to go out with him when he came courting in madras pants, “and she didn’t understand them at all.”

Menswear author Bruce Boyer, who in the early ’60s attended Moravian, one of America’s oldest colleges, agrees that bright WASP leisurewear is probably a countermeasure to drab Monday-to-Friday garb. “It used to be said that the man in the gray flannel suit was so color deprived that on the weekends he went crazy on the golf course,” says Boyer. “If you’ve got to wear a black and white wardrobe most of your life, maybe you go crazy in the other direction with fuschia corduroys and a turquoise shetland crewneck.”

“It’s certainly ironic,” adds Flusser, “how this look derived from the most conservatively dressed people in other circumstances.”


Brooks Brothers and J. Press, founded in 1818 and 1902 respectively, have for generations been the leading purveyors of the Ivy League Look, and during the heyday, their shops freely juxtaposed colorful leisurewear with the grey-suit uniforms of the Atomic Age company man.

“One of the great things about Brooks Brothers is that side by side with three-piece grey flannel suits were ancient-madder dinner vests and The Fun Shirt,” says Flusser, referring to the retailer’s famous patchwork-striped casual shirt. “So out of this bastion of conservatism was born this outrageousness that WASPs — and also Jews — came to adorn themselves in. It wasn’t fashion stores, but the oldest-money, most proper places where you could buy this stuff.”

In “Style and the Man,” his 1996 guide to the world’s finest menswear purveyors, Flusser describes Brooks Brothers’ whimsical offerings:

To most outsiders, Brooks was a stronghold of conservatism and dry style, but to those of the gray flannel life who frequented country clubs or other Ivy League settings, Brooks was also one of the primary wellsprings of the preps’ ‘king of the hill’ party clothes. Around the horn-rimmed set’s many private playgrounds, the stylish button-downers would engage in a form of sartorial one-upmanship that brought wild dollops of golf course color or tartan-inspired outrageousness into classic ensembles that made insiders smile while outsiders winced. It was not aberrational to spot some young prep sporting maize corduroys, blue-striped oxford button-down, repp tie, tweed jacket, brightly colored socks, and tasseled loafers. Pink and peach oxford button-downs were accessorized in combinations that made the whole look masculine and handsome.

Of J. Press, founded in New Haven, Connecticut near Yale University, Flusser writes, “This style of dressing still employs punches of strong color to idealize the spirit of buoyancy and optimism of the American traditionalist.”

“Ivy Leaguers take themselves quite seriously,” notes Denis Black, manager of J. Press’ Boston store.  “But when they have a festive occasion, they like to show up like they work for Ringaling Brothers. They come dressed like that at Harvard commencement, or for the Harvard-Yale football game. They all work for important firms where they’re stodgily dressed, and want to unwind on the weekend in kelly green corduroy pants with a bright yellow shetland sweater.

“That kind of stuff is very important for J. Press,” adds Black, “and is a signature of this style of dressing.”


Amid the green pants and yellow sweaters stands the most notorious and damnable item in the go-to-hell wardrobe: the critter pant, or trousers emblazoned with an embroidered motif. Often based on sailing and oceanic imagery, such as anchors, whales or lobsters — or in rare instances one leg with lobsters and the other with bowls of butter sauce — critter pants are as baffling to most Americans as they are to the rest of the world.

“I don’t know what the first embroidered motif was or where it came from,” speculates Flusser, “but it certainly came off a necktie design, there’s no question about that.” Lacoste’s crocodile emblazoned on polo shirts was the first embroidered logo, Flusser points out, and it, combined with club-tie designs, was the likely inspiration for the first pair of critter pants.

Paul Winston says it wouldn’t surprise him if his father Sidney invented embroidered pants. Winston, now 76, is a New York-based custom tailor who in the early ’60s began working for Chipp, his father’s legendary menswear shop that, along with Brooks Brothers, J. Press and Paul Stuart, formed the cluster of traditional clothiers centered around 44th Street and Madison Avenue. For its embroidered pants (or skier-emblazoned sport coats, as in the case of IBM’s Thomas Watson, Jr.), Chipp made sure to use lock-stitch embroidery. “With other pants, if you sat on a rock on the beach and snagged one of the lobsters or frogs,” Winston says with a chuckle, “the whole thing would pull out. But ours wouldn’t do that.”

Chipp is also the company most credited with the patching of madras, seersucker and tweed, which began when Sidney Winston got the idea of using leftover scraps of fabric, sewing them together like a quilt, and making trousers and jackets from it. Patching soon became one of Chipp’s trademarks, though not in the literal sense: Winston has reaped no royalties from mainstream retailers’ many patch-madras offerings the past few seasons.

At O’Connells, Ethan Huber recalls such embroidered motifs as cigar-smoking pigs (the capitalist sort, of course), and mysterious acronyms such as “SYLA” (for “See Ya Later, Alligator”) paired with alligators, and BTEB (“Behind the Eight Ball”) paired with ominous black billiard balls. Onlookers would think the recondite lettering suggested some secret club.


It’s worth noting that Wolfe’s “go-to-hell” passage describes not only the accursed trousers themselves, but how they’re worn. For Flusser, this is the most elusive aspect of dressing. “You can take any article of clothing and wear it,” he says, “but that doesn’t mean to do so is stylish. The important thing about wearing a bright colored trouser is knowing how to wear it: building an outfit around one discordant pattern or color, and surrounding it with things that present it.”

In the eyes of the tribe, the “right” way to wear a hellbound item is to pair it  with otherwise “correct” clothing. “You wouldn’t wear wild-colored embroidered pants with a brightly checked shirt,” says Boyer. “You’d wear a blue, white, yellow or pink oxford-cloth buttondown. But bright pants with a bright shirt would be interpreted not so much as bad taste, but as breaking the code.”

Likewise, a color’s shade has to be just right, as in the special shade of pink that distinguishes a Brooks Brothers oxford from its imitators, or the perfect fade on a pair of Nantucket Reds, indicating years of summers spent sailing. And certain colors, such has purple, have found little place within the genre.

Though a silly piece of Hollywood prepsploitation, the 1984 film “Making the Grade” is nevertheless illustrative of the ethos surrounding garish clothes as worn in a WASPy milieu. Set at a New England prep school, the film includes a school dance scene in which students wear a plethora of Crayola-colored and audaciously patchworked pants and blazers. Yet not only does not a single character show any self-consciousness about what he’s wearing, he’s also completely oblivious to the harlequin garb of his peers.

At least that’s how it seems. “There’s a very conscious, planned nonchalance about this style of dressing,” says Boyer. For WASPs bring to colorful plumage the same tempered restraint and calculated disregard they bring to all other aspects of life. Ironic dressing is completely foreign to a group of people utterly devoid of an ironic sensibility. Sure, the clothes are obnoxious, but they’re also “correct.” If there’s such a thing as earnest irony, this is it.


Long since made mainstream — and perhaps saved from extinction — by Ralph Lauren, clothing that’s go-to-hell in spirit is still worn by the remnants of its founding tribe. And oddly enough, one of the places the infernal clothing is brought out most frequently is at Sunday worship.

“Deliberately outlandish WASP clothing is still outside the public view in certain pockets of Washington DC,” says an anonymous political insider, “especially during the hot summer. At my Episcopal church, I recently saw a gentleman in his late 50s wearing a patch-madras sport coat, Nantucket Red shorts and Weejuns without socks. Evidently it was good enough for God.”

God, like the rest of the tribe, probably didn’t even notice. “In a world where everyone is wearing Nantucket Reds or corduroy pants embroidered with lobsters,” says Lisa Birnbach, “it’s really not that big a deal: One’s eye adjusts.” Birnbach’s 1980 bestseller The Official Preppy Handbook makes note of a particular genetic defect among preppies, namely “specific color blindness,” which leads to “primary colors and brilliant pastels worn indiscriminately in preposterous combinations.”

The whole point is to have an insular code, says Birnbach. “Whether it’s slang or clothing, it’s a way to identify one another in one’s group — and many of these Old Guard, WASPy types weren’t particularly interested in knowing people from another group.”

Satiric in tone and purpose, The Official Preppy Handbook at one point suggests readers use pink and green crayons to color a black and white illustration. And in this quintessential preppy color combination (not surprising, the official colors of the prep school in “Making the Grade”), is the seed of preppy’s own undoing, the point at which the scale tips from style to satire, from cultural expression to marketplace pastiche. It’s the IBM gray-suit, white-shirt joke all over again, but for a new generation and with a different punchline.


Because those viewed as privileged make for easy targets, and because the elements of the style are so fixed, WASP whimsy lends itself to easy parody, most recently and notoriously in the Smirnoff “Tea Partay” commercial, a YouTube favorite. Here pastel clothing is used not for the tribe to differentiate itself from outsiders, but for outsiders to lampoon the tribe. Time passes, the old order withers away, and an age of irony engulfs us all. The tribe, plagued by a tragic flaw, relinquishes its power, and the rest of society, like characters in an archetypal myth, overthrow the tyrants and don their vestments.

Even more odious, today the best-selling Nantucket Reds at Murray’s Toggery Shop are the pre-faded version, for those unaware that patience is a virtue.

For Boyer, taste and tradition, rather than emanating naturally from a land of authenticity, have become just another commodity to be hawked in the marketplace. The mass availability of preppy style today can be read either as a sign of the omnipotence of egalitarianism, or as the last example in fashion of taste coming from the top down, rather than the bottom up. “Capitalism is a great engine of democratization,” notes Boyer.

O’Connells’ Ethan Huber adds the retailer’s perspective: “In the ’80s there was an incredible amount of business we did with madras and go-to-hell pants. Now there’s another resurgence, and you have madras at Wal-Mart.”


Like an Old Money family that returns each year to its summer home, let us revisit Martha’s Vineyard, scene of Tom Wolfe’s Boston Brahmins and their go-to-hell pants.

In 1998, a couple of Wall Street guys decided to start a clothing brand. They named it Vineyard Vines, and opened a retail store on the island retreat. Originally based on colorful motif ties, the company now carries a full collection of bright sportswear that strikes many world-weary eyes as an over-the-top preppy caricature. Between 2003 and 2006, the company’s annual revenues grew from $5.7 million to $37.2 million.

The Vineyard Vines website includes a section with hundreds of photos of customers dressed in the brand’s bright colors and whimsical designs. It’s as sure a sign as any that we’re all going to hell. Quotes

From Paul Fussell’s “Class”: Go-to-hell in spirit also are the sports or playtime trousers which identify the upper-middle class, especially the suburban branch. One common type is white duck trousers with little green frogs embroidered all over them. A variation: light-green trousers, with dark-blue embroidered whales. Or signal flags. Or bell buoys. Or lobsters. Or anything genteel-marine, suggesting that the wearer has just strolled a few steps away from his good-sized yacht.

From Lauren Lipton’s “Mating Rituals of the North American WASP”: What do you call those preppy pants, the kind where the right front leg is, like, yellow, and the left front leg is pink, and the right back leg is, I don’t know, green and the left back leg — ” “Go-to-hell pants,” Luke interrupted. “What’s your point?” “You people are lunatics,” Bex scoffed. “You can wear pants like that, but you won’t say one little ‘I love you’?”

M. magazine, 1990: A prime reason WASPs like meeting people and socializing…. is that it gives them the chance to prove what daring fellows they are.  All WASP men have “go-to-hell” clothes for such occasions, usually poisonous green pants with little whales or anchors printed on them.  Even though they wear dumb clothes to the office, WASPs with real guts always include one “go-to-hell” item, in their business attire too. Nelson W. Aldrich, Jr.,”Preppies: The Last Upper Class?”

Atlantic Monthly, 1979: Preppies of all ages and both sexes demonstrate an unwavering taste for luminescent pastels and hard primary colors, a taste evidently designed to evoke the infantile gaiety of the nursery or the youthful certainties of Playskool.

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