Doc Martens, Skinny Jeans, Leather Jackets and More From America’s Fashion Wars

Fashion is often reduced to a series of irrational swings. Hemlines rise and fall. Trousers get slimmer or fuller. But more than just trends, fashion is a type of social language often used as a marker of identity. Codes, as cultural theorist Stuart Hall noted once, “cover the face of social life and render it classifiable, intelligible and meaningful.” Clothing works in the same manner, and the history of dress can easily be read as a series of battles around identity—race, class, gender and sexuality. The meaning of these codes changes over time: One group picks up a garment, another moves on. Perhaps the best way to understand how America has always fought its culture wars is through our wardrobe.

In the early 2000s, slim-fit jeans with tidy, upturned cuffs, commonly paired with pristine work boots and tight flannel shirts, were a new look in certain corners of the US. Fashion-conscious men of this era wore skinny jeans as a way to challenge the previous decade’s gender norms, when the idealized masculine body ranged from lean athletic to body-building muscular (think Abercrombie & Fitch and Arnold Schwarzenegger, respectively). This new style, called “metrosexual,” became a flashpoint for a new culture war around gender, as conservative Americans questioned whether things such as skin-care routines, jewelry and skinny jeans were a sign of decay in Western masculinity.

About 10 years later, Levi’s celebrated this literal and figurative crossing of gender lines by introducing the Ex-Girlfriend cut, a new skin-tight jean silhouette for men, in 2011. The cut was endlessly mocked online. Stephen Colbert gave it his “wag of the finger.” Time asked, “[W]hat kind of boyfriend slips into his girlfriend’s skinny jeans in the first place?” The New York Times added, “Indeed, the only thing a woman likes more than a man wearing her pants is a man wearing a tribute to his ex-girlfriend’s pants.”

More than 20 years later, skinny jeans are so common that you can find cotton-poly stretch versions at Goodfellow & Co., one of Target Corp.’s in-house labels. The ubiquity of this spray-on fit has cost the style its original edginess. Conservative men now wear skinny jeans in the latest moral panic about gender practices. When Candace Owens interviewed right-wing commentator Matt Walsh—not once, but twice—the Daily Wire host wore skin-tight jeans that gripped his figure.

When Americans shipped off to fight in World War II, many departed from California’s shores. In Los Angeles, rowdy servicemen eager to let off steam often caused a ruckus in neighborhoods, creating tensions between them and local Mexicans and Mexican Americans. This came to a head in June 1943 when a convoy of servicemen, most of them Navy personnel, went looking for “zoot suiters,” young men who wore flashy garments in exaggerated proportions. The extra fabric expressed, in the eyes of the military men, a lack of patriotism for using so much textile during the war. That night, they stormed a downtown theater and beat a group of mostly Latino youths, some as young as 12, with clubs, chains and gun belts, leading to an explosion of racialized violence, events that would later be collectively known as the Zoot Suit Riots.

Zoot suits originated far from California’s shores, though. In the early 20th century, a Dutch-English tailor named Frederick Scholte in London noticed that if you belt up a guardsman’s coat, the chest looks fuller and rounder, making the wearer appear more athletic. He devised a cutting method to incorporate this effect into his suits, inventing what’s now known as the “drape cut,” which features slightly extended shoulders, a fuller chest with excess material near the armholes and a nipped waist to give the impression of a stronger, V-shaped figure. Scholte would soon become one of the most sought-after tailors in British high society, making clothes for the Duke of Windsor and training Peter Gustav Anderson, co-founder of Anderson & Sheppard. The drape cut also caught the attention of Hollywood luminaries like Fred Astaire, who was known to twirl and glide across Anderson & Sheppard’s fitting rooms to ensure his jacket’s collar never lifted off his neck when he was dancing.

During the Jazz Age, elements of the drape cut found their way into the nightclubs of Harlem, where its signature features became exaggerated. The shoulder lines became more generous: padded, high-waisted, balloon-shaped trousers with knife-edge pleats billowed from the thighs: suit jackets cascaded down to the wearer’s knees; and chests looked like wind-filled sails. By wartime, this sartorial spectacle, by then known as the zoot suit, migrated to the sock-hopping teens in Chicago and eventually landed on California’s coastline, where it became the preferred attire of Mexican Americans known as pachucos. Decades after the 1940s racial attacks, many Americans have forgotten the racial and class elements associated with that look, and only remember it as something worn by stylish jazz greats such as Cab Calloway.

When brothers Irving and Jack Schott designed the first motorcycle jacket in 1928, they built the garment around function: an asymmetrical zip that would block wind, a snap-button collar that could be fastened to the neck, and material cut from heavy horsehide or cowhide to protect the wearer from unforgiving pavement. Their jacket, dubbed the Perfecto, replaced the leather aviators that motorcyclists wore in the early 20th century. But in 1947, the leather motorcycle jacket transformed from being a simple utilitarian garment to symbolizing a new American menace.

That summer, a procession of 4,000 bikers thundered into Hollister, a small California farming community hosting its annual Fourth of July carnival. Members of motorcycle clubs such as the 13 Rebels and the Pissed Off Bastards of Bloomington descended upon the rural town, engaging in brawls, shattering store windows, participating in illegal drag races and overrunning the small local police force. Life magazine soon published an exposé titled “Cyclist’s Holiday: He and Friends Terrorize Town.” The article featured an image of a young biker, later identified as Eddie Davenport, slouched astride his Harley-Davidson, shirt open and surrounded by smashed beer bottles. Notably, he was pictured wearing what seemed to be a naval deck jacket—a possible indicator that he, like many, was an ex-serviceman who found solace in motorcycle organizations upon returning home from war. Debates persist regarding whether subsequent media coverage inflated the extent of violence and destruction, but this event indelibly transformed the perception of black leather jackets in the eyes of the nonriding public.

From that point on, black leather jackets became the very essence of rebellion—a powerful symbol of anti-conformity, inner turmoil and an aversion to the rules of law. In quiet corners of small towns, residents fretted over the specter of motorcycle “hoodlums” and the prospect of destructive escapades. The indelible image of the leather-clad rebel found its apotheosis in Marlon Brando’s role in the 1953 classic, The Wild One. This symbolism continued through the 1970s and ’80s when punks such as Sid Vicious wore studded motorcycle jackets with skin-tight jeans, metal chains and spiked hair.

Today, the black leather motorcycle jacket is a form of professional dress, particularly for women. Political figures such as Cindy McCain, Sarah Palin and Alexandria Ocasio-Cortez, wear leather motorcycle jackets during television appearances. Executives such as Michelle Gass (president of Levi Strauss & Co.), Adena Friedman (chair and chief executive officer of Nasdaq) and Mary Barra (CEO of General Motors Co.) have worn it in lieu of a blazer. The motorcycle jacket still stands for power and strength, but by transitioning into a luxury item that elites wear, it’s lost some of its countercultural subversiveness and sense of danger.

The irony of the Army jacket is that, during the 1960s and ’70s, it served two purposes. For Americans battling in Vietnam, the Army jacket was a protective cover; for antiwar protestors at home, it was used as cultural commentary. Dissenting youths carrying “Get Out of Vietnam” placards wore Army jackets with white jeans while marching through the streets of Oakland and Berkeley in 1965. Country Joe at Woodstock and John Lennon at Madison Square Garden wore Army jackets while performing in front of cheering audiences. When Jane Fonda toured the country on her FTA roadshow (“Free the Army,” a play on the popular trope “F- – – the Army”), she appeared onstage in battle dress.

Vietnam War veterans wore their Army jackets when they protested the war in 1971, throwing their medals and discharge papers onto the steps of the US Capitol. When Navy Lieutenant John Kerry—a future US secretary of state—returned home from Vietnam, he used his Army jacket as a protective shield while criticizing US foreign policy. The jacket during this period was as much about commentary as it was about function, having been used for battle abroad and enlisted in antiwar efforts at home.

Since the Vietnam War, the Army jacket has evolved to represent even more personae. On Al Pacino in Serpico, it was the badge of unwavering integrity; on Robert De Niro in Taxi Driver, it was the protective cocoon of a loner. Tony Sylvester, a British singer and owner of the menswear brand AWMS, says the Army jacket has collected so many different layers of meaning that “no one assumes you’re a soldier anymore when you wear one.” During an interview with Bloomberg Businessweek, he said, “There’s so much cultural language embedded in it, people are more likely to assume you’re wearing it for countercultural reasons than the reason why it was made.”

German doctor Klaus Märtens had a revelation after he injured his ankle in a skiing accident in 1945 and found that he could no longer comfortably wear his standard-issue Army boots. While convalescing at home, he figured that boots could be made more comfortable if they were built on an air-cushioned sole, forming something like a hybrid between military boots and sneakers.

That was the seed of Doc Martens, as the shoes became known over time: Märtens and a university friend formed a small shoe company in 1947, which was popular with women in their 40s, mostly housewives. The partners eventually sold their air-cushioned technology in 1960 to the R. Griggs Group, a British work boot manufacturer located in Northamptonshire, who reshaped the heel, added the trademark yellow stitching and introduced the boots as “Dr. Martens,” an anglicized version of the original German doctor’s name. The first Dr. Martens boots were cheap, and their affordable price point and comfortable, air-cushioned soles made them popular with Britain’s working classes, including mail carriers, police officers and factory workers.

What starts on the street eventually makes it onto the stage, and Pete Townshend of the Who was the first major-profile figure to wear Dr. Martens while performing in 1967. He later said that he disliked the foppish clothes available at the time and wanted something utilitarian he could wear while bouncing around and playing his guitar. Other rebellious groups—scooter riders, mods, punks, goths, glam rockers, psychobillies—also took to them, a group that unfortunately included racist skinheads, who laced them up with red or white laces to signal their White power ideology. Dr. Martens’ association with violence made them controversial in the 1990s, including an incident in a quiet Dallas-Fort Worth suburb, where school authorities pulled students out of classrooms for wearing industrial-looking Doc Martens boots with steel toe caps—a detail seen as potential weaponry.

By the 1990s, the work boot went from being a symbol of violence, empowerment and anti-establishment individuality to the height of teenage mall-fashion conformity. They appeared on the television show Friends; Claire Danes wore them in My So-Called Life. Dr. Martens still stands for counterculture, but the boots have lost much of their edge as the corporate class has so thoroughly co-opted them. Today, the company sells tiny, infant-size versions of the iconic boots to new parents.

In the 1990s, LL Cool J, Tupac Shakur and other rap artists took a style that was already popular on the street—worn mainly by Black men in urban centers—and flaunted it in music videos and the covers of magazines like the Source. Baggy pants, worn halfway down the wearer’s rear—typically with overly long inseam lengths stacked on top of Timberland boots or chunky sneakers—carried a kind of cavalier swagger that has shaped American style ever since Brando struck a rebel pose in The Wild One.

What was a symbol of defiant machismo for some, however, was a mark of criminality for others. In May 2004, Bill Cosby delivered a speech urging Black Americans to stop blaming racial disparities on the legacy of slavery and institutional racism and instead to examine their own cultural practices. “Are you not paying attention?” he asked. “People with their hats on backward, pants down around the crack, with names like Shaniqua, Shaligua, Mohammed and all that crap, and all of them are in jail.”

Sagging pants were controversial in the 1990s, but they took center stage during the mid-2000s. In 2007, the Town Council of Delcambre, Louisiana, enacted an indecent exposure ordinance banning the wearing of pants slung so low that they revealed the person’s underwear. The next year, the local governments of Pagedale in Missouri and Hahira in Georgia issued similar ordinances. The interim police chief of Flint, Michigan, even ordered the arrest of saggers for disorderly conduct (although, in the end, only warnings were issued). Speaking in an interview on MTV, then-presidential-hopeful Barack Obama said he thought these measures were a “waste of time,” adding, “Having said that, brothers should pull up their pants.”

The debate continued with headline-catching controversies, like a middle school in Memphis that threatened to “Urkel” saggers (secure their jeans with zip ties) and post their photos in the hallways for public humiliation. The urgency around sagging has faded with time, replaced by, among other things, a more fulsome cultural conversation about hoodies. By the time Cosby was arrested for sexual assault in 2015, discussions around pant sagging had become a distant memory.

Before the gay liberation movement of the 1960s, gay men and lesbians were more strongly pressed to “pass” as heterosexuals; an unwanted outing could mean arrest, or worse. Many people used clothes to subtly signal their sexual orientation so they could find community and even love. “The adoption of a series of secret codes allowed gay men and lesbians to spot each other while remaining invisible to the outside world,” Shaun Cole, author of Don We Now Our Gay Apparel, wrote in GLBTQ.

In the 1890s, gay men in London wore an artificially colored green carnation in their lapel to symbolize, as Lord Alfred Douglas put it, “the love that dare not speak its name.” The accessory, initially popularized by his lover Oscar Wilde, became a discreet hint of an underground world where “rent boys” plying their trade in London’s Piccadilly Circus wore green carnations to attract customers. By the turn of the 20th century, gay men signaled their sexuality through white gloves and pinkie rings. During the interwar years, it was red ties (something George Chauncey documented in his book Gay New York). For a while, in France, it was a green cravat; in England, it was pale blue socks. Even pointy suede shoes were a “quiet wink at the initiated in the same way an offhand reference to Judy Garland could determine whether a stranger was a fellow ‘friend of Dorothy,’” wrote Max Mosher in The Worn Archive. The codes worked so well that early researchers, baffled at gay men’s ability to find each other, theorized some sort of homosexual “sixth sense.” In reality, many wore their identity on their sleeve.

By the 1970s, green cravats and red neckties migrated to the back of men’s pockets, eventually to be replaced by color-coded handkerchiefs. According to the book Gay by the Bay: A History of Queer Culture in the San Francisco Bay Area, the trend supposedly started after a Village Voice writer joked that, instead of hanging a set of keys on the left or right side of one’s body—then a common code to indicate whether someone was a “top” or “bottom”—they could wear colored bandannas instead. (In Larry Townsend’s The Leatherman’s Handbook II, a chart decodes each color: Navy represented anal sex, light blue stood for oral sex and black was for S&M.) The practice, known as “flagging,” became popular in the gay communities of New York City and San Francisco.

Despite the marginalization of the LGBTQ+ community, its style trends have often seeped into mainstream fashion. Slim-fit flannel shirts with Red Wing boots and raw denim jeans with the cuffs neatly rolled went mass market with retailers such as J.Crew in the mid-2000s. (Frank Muytjens, then the head of J.Crew’s men’s design, said the company started selling Red Wing because he liked how the boots looked on lesbians in New York’s Chelsea neighborhood.) In more recent years, straight men have picked up the airy, sheer shirts once seen in International Male, a mail-order clothing catalog popular with gay men.

When the sportswear company Champion introduced the first hooded sweatshirt in the 1930s, its primary customers included footballers trying to stay warm on the sidelines and New Yorkers operating forklifts inside frigid warehouses. By the 1960s and 1970s, it ascended from utilitarian garment to a cloak of inspiration—first with Muhammad Ali photographed sprinting through the streets of London with a hoodie tightly pulled over his face, then as the uniform for an aspiring boxer in Rocky.

In the 1980s, the hoodie underwent a transformation, integrating itself into youth street culture. It became the preferred garb of graffiti artists and punks, enjoyed favor among influential rappers such as members of Run-D.M.C., and was embraced by young skaters and surfers who used Southern California’s shoreline as their playground. As the hoodie resonated with Black teenagers and countercultural white youths, it began to symbolize all that made the middle classes uneasy: perceptions of disorder, idleness and delinquency.

The stigma attending Black men in hoods came to a head in 2012 with the killing of Trayvon Martin, an unarmed Black teen wearing a charcoal hoodie on a drizzly night when George Zimmerman fatally shot him in an Orlando suburb. His death threw the hoodie into a national debate. Supporters of the Martin family pointed to the assumptions that many made about hooded faces and users on Facebook and Twitter changed their profile pictures to images of them or their children wearing hoodies. The Miami Heat basketball team, former Michigan Governor Jennifer Granholm and Marian Wright Edelman of the Children’s Defense Fund also posed in hooded sweatshirts. “The hoodie is a way of expressing support for the Martin family,” Granholm told NPR, “and for all the sons of African American families who bear the heavy burden of other people’s negative assumptions.”

Perceptions of the hoodie, however, are never about the garment itself but how it looks on the body underneath. During the early 2000s, Mark Zuckerberg and tech personnel turned the hoodie into an emblem of Silicon Valley meritocracy—workwear that rebelled against the coat-and-tie status quo of corporate America. As Troy Patterson wrote in the New York Times Magazine, “The lingering question of the hoodie is simply: Who enjoys the right to wear one without challenge?””

Brands often invest a lot of effort to integrate themselves into the identities of certain groups, but not all sales are welcomed with open arms. Utah-based Pit Viper LLC has been making 1990s-style sport sunglasses since 2012. The company pitches itself as being carefree and fun-loving—more about beer and bros than politics and social issues. But in the past few years, the company has been “hatejacked,” a term for when fringe groups adopt a product and create an image problem for the brand, as when members of the White supremacist group Proud Boys decided to don Fred Perry shirts. (In 2020, Fred Perry stopped selling those shirts for this very reason.) Far-right figure Baked Alaska wore Pit Viper sunglasses at the Jan. 6 insurrection; White supremacist Nick Fuentes sports them on his livestreams.

In response, Pit Viper has had to delicately thread a needle, trying to shake off an unwanted association without being so political as to ruin its products’ fun vibes. To make its position clear, the company created a “Pit Viper Gives a F*ck” campaign that donates a portion of its profits to various causes: “support for war veterans, equality for the LGBTQ+ community, food for the hungry, resources for the underprivileged and equality for marginalized groups,” its site says.

In 2022, Pit Viper also released a special pair of Pride-themed sunglasses, donating proceeds to the Trevor Project, a nonprofit aimed at preventing suicide among LGBTQ+ youths. It also took to X, the platform formerly known as Twitter, to post this: “Any website wiz-types out there who know how to prevent racist losers from buying your product? asking for Nick Fuentes, who needs to stop wearing Pit Vipers.” This brand, like so many before it, had to learn that the meaning of your apparel will always depend on who’s wearing it.

(Corrects Adena Friedman’s title in the 11th paragraph.)