[Clothes make the man (and woman, I warrant), some people believe. Maybe so, but Vanessa Friedman, fashion director and chief fashion critic of the New York Times, wonders what that looks like, especially with the changing fashion of the oft-invoked American Dream.
[That’s actually her job. She chronicles what clothing says about American women and men over the past two-and-a-half centuries. Of course, Friedman doesn’t look at li’l ol’ you and me. She looks at the people who make fashion.]
“250 YEARS OF
DRESSING FOR THE AMERICAN DREAM”
by Vanessa Friedman
[Vanessa Friedman’s article appeared in the New York Times of 5 July 2026, in the “Sunday Styles” section. An undated (probably 6 July), cut-down version (with photos, but severely edited text), under the same headline, is posted on the Times website.
[The only other online version of the article with the complete text that I could find is on the ProQuest New York Times database on the New York Public Library website; if you have access to this service through your library, it’s at 250 Years of Dressing for the American Dream: [Style Desk] - New York Times - ProQuest (text only).]
Over 250 Years, What We Wore To Break Free And Show Off.
For 250 years the American dream has been fodder for a potent national brand. Little wonder that since he began running for president, Donald J. Trump [b. 1946; 45th President of the United States: 2017-21; 47th President: 2025-2029], perhaps the most active executive brand manager in history, has repeatedly invoked the idea: declaring it dead, positioning himself as its champion, announcing it has been restored.
Often he seems to be talking about a purchase of some kind, like a home, a yacht, a freshened-up face, an ever more gilded fantasyland of success.
Yet when the American dream — or at least the idea that later became the American dream — was born along with the country, it looked very different.
Initially defined by the founders as “life, liberty and the pursuit of happiness,” that dream was reimagined by each generation and wave of immigrants. As a collection of values (like any brand) it often had less to do with material value than abstract values like liberty, revolution, aspiration, security and reinvention.
Perhaps the best way to think of it is as a “mythic construct,” said Jim Cullen [b. 1962], the author of “The American Dream: A Short History of an Idea That Shaped a Nation” [Oxford University Press, 2004]. One in which, he said, “freedom is the currency of self-realization, which gets reflected in outward presentation that ratifies one’s hope, or one’s status in culture.”
In other words, one way to understand the way the American dream has evolved may be to consider the different styles Americans designed for the world they were inventing.
Freedom and Revolution
It began with the chance to define a new set of laws and governance, to reject the inherited trappings (or traps) of class.
“To escape from Old World fetters and start over again,” said Sean Wilentz [b. 1951], a professor of American history at Princeton University and author of “The Rise of American Democracy: Jefferson to Lincoln” [W. W. Norton & Company, 2005].
The founding fathers dressed the part, taking their cues from the fashions of Britain and France and simplifying them.
“In terms of silhouette, in terms of embellishments, there was always a sort of underlying sense of, not puritanism per se, but pulling back,” said Andrew Bolton [b. 1966], the curator in charge of the Costume Institute of the Metropolitan Museum of Art and the man behind the show “American Woman: Fashioning a National Identity” [5 May-10 August 2010].
George Washington [1732-99; First President of the United States: 1789-97] may have powdered his hair, but he rejected the wig. Benjamin Franklin [1705-90; a Founding Father of the United States], who built a printing empire in Philadelphia, “was as attuned to self-presentation as anyone in American history,” Cullen said. It was not an accident that when he was ambassador to France, Franklin represented his country with a beaverskin cap.
He understood the story that was being constructed had to do with the promise of new frontiers. A century later, the same promise was embodied by Buffalo Bill [aka: William Cody; 1846-1917; soldier, bison hunter, and showman] and his fellow pioneers, who helped build the myth of the West and created an enduring style of their own, albeit one that borrowed heavily, and without acknowledgment, from the Indigenous cultures that were being displaced. Throughout the 1800s, that myth helped turn functionality and practicality into a virtue in dressing symbolized by the jeans [aka: “Levi’s”] invented by Levi Strauss [1829-1902; German-born American businessman; founded Levi Strauss & Co. in 1853].
That same spirit was adapted by the Gibson girls of the late 19th century, whose clothes reflected a newfound independence and love of action, captured for posterity by artist Charles Dana Gibson [1867-1944; illustrator for magazines and books], whose work gave them their name. And it was taken to an even further extreme by the flappers of the early 20th century, represented by Clara Bow [1905-65; film actress in silent films and early “talkies”] and Josephine Baker [1906-75; American-born French dancer, singer, actress, and spy for the French Resistance], who rejected the corset with all its real and metaphorical limitations in exchange for unprecedented physical emancipation. Four decades later, the hippies would carry that torch, shrugging off fashion niceties the way they shrugged off antiquated ideas about sex and society.
[The Gibson Girl was the personification of the archetypal feminine ideal of physical attractiveness as portrayed by Gibson’s pen-and-ink illustrations that spanned the late Gilded Age [from about the late 1870s to the late 1890s] and Progressive Era in the U.S., from the 1890s to the 1920s. The character became iconic and came to embody the concept of the New Woman.
[Flappers were a subculture of young Western women prominent after the First World War (1914-18) and through the 1920s who wore knee-length skirts (then considered short), bobbed their hair, listened to jazz, and flaunted their disdain for prevailing codes of decent behavior. Icons of the Roaring Twenties, flappers have been seen as brash for wearing excessive makeup, drinking alcohol, smoking cigarettes in public, driving automobiles, treating sex in a casual manner, and otherwise flouting social and sexual norms.
[Hippies (for those too young to remember the ‘60s) were followers of a youth subculture associated with the counterculture of the mid-1960s to early 1970s that began in the United States. Hippies were the generation that followed on the beatniks (fl. 1950s). The hippies of the 1960s and 1970s inherited the Beat Generation’s rejection of materialism, embrace of Eastern religions, and interest in altered states of consciousness—though they carried the Beats’ style, scale, and substance several steps further. While the black-clad beatnik was dark, cynical, and emotionless, the tie-dyed hippie was sunny, joyful, and enthusiastic.]
At the same time, the Black liberation movement [mid-1960s through the end of the 1980s] created a modern version of the militant, challenging conventional notions of what rebellion looked like. Their disciplined fashion communicated a powerful message of revolutionary intentions and solidarity.
Affluence and Aspiration
Still, the term “American dream” wasn’t officially coined until 1931, when the popular historian James Truslow Adams [1878-1949; writer and historian] wrote the best-seller “The Epic of America” [Little, Brown, and Company, 1932]. It codified the idea of the dream as “a land in which life should be better and richer and fuller for everyone, with opportunity for each according to ability or achievement.” Which later came to mean material attainment and conspicuous consumption.
“Making it was a big part of it,” said Valerie Steele [b. 1955; fashion historian, and curator], the director of the Museum at the Fashion Institute of Technology [a division of the State University of New York, in Manhattan, New York City]. Or rather, being “self-made.”
The foundation was originally laid by the second and third sons of the British aristocracy who emigrated to the new colonies [from the mid-17th through the 19th centuries] to build the estates that primogeniture denied them. In the south especially, they recreated the grand homes and the elaborate fashions of England (as well as its worst caste structures). Later the trappings of immense and visible wealth became the provenance of the self-made men of the gilded age, whose fortunes ushered in the era of generational wealth and created an archetype that was, Bolton said, “exported around the world.
“Henry James [1843-1916; American-British author] wrote about it, Edith Wharton [1862-1937; writer and designer] wrote about it,” Bolton said. All that opulence in environment and fashion was preserved in oils by John Singer Sargent [1856-1925; American expatriate artist; considered the leading portrait painter of his generation] and William Merritt Chase [1849-1916; painter; known as an exponent of Impressionism]. A more exuberant counterpoint was created during the Harlem Renaissance of the 1920s, which challenged stereotypes and canonized Black style. Zoot suits, silk, satin and pearls dominated the dance floors.
[A zoot suit is a men’s fashion ensemble featuring a long, broad-shouldered jacket and high-waisted, wide-legged pants. Originating in African-American comedy shows of Black vaudeville in the 1920s, it became an iconic, rebellious cultural symbol for African-American men in the 1930s. it later became popular with Mexican, Filipino, Italian, and Japanese Americans in the 1940s, who used the dramatic, defiant style to assert their visibility and independence.]
The second gilded age arrived in the 1980s [through the 2010s], with a bigger-is-better ethos reflected in the grand talk and grander shoulders of the time, all of it memorialized in Tom Wolfe’s [1930-2018; author and journalist] “Bonfire of the Vanities” [Farrar, Straus and Giroux, 1987] and embodied by the taffeta-clad gala-going wives of the new Wall Street robber barons.
By the late 1990s, the video maestro Hype Williams [b. 1970; music video and film director, film producer, and screenwriter] was ushering in the shiny suit era of hip-hop, followed by Jay-Z [b. 1969; rapper, businessman, and record executive] and Co., sailing into the sun on a mega-yacht in “Big Pimpin’” in 2000 [song by Jay-Z from his 1999 album Vol. 3... Life and Times of S. Carter; released as a single]. As the millennium turned, bling and brands were remixed into cultural currency by artists like 50 Cent [b. 1975; rapper, actor, television producer, record executive, and businessman], Missy Elliott [also known as Misdemeanor; b. 1971; rapper, singer, songwriter, and record producer], Biggie Smalls [also known as the Notorious B.I.G.; 1972-97; rapper and songwriter] and Lil’ Kim [sic; b. 1974; rapper, singer, songwriter, and model; referred to as the “Queen of Rap”], who built images and empires out of the totems of the one percent.
Security and Reinvention
Along with financial success came another version of the American dream, one that had less to do with bling and more to do with security. It was a sense of belonging expressed through assimilation, as well as the acquisition of actual belongings.
It was after 1945, Wilentz said, when snagging the brass ring started to resemble “owning your own home, preferably in the suburbs, having stable year-round employment and making sure your children would do better than their parents’ generation.”
In the 1950s, that fantasy took the real-life form of the man in the gray flannel suit, picket fences and poodle skirts — at least until Doris Day [1922-2019; actress and singer; known for her girl-next-door image on screen] gave way to the dependably preppy style of the Ivy League. In the early and mid-1960s, the Kennedy clan dressed up their political ambitions in the crew necks, polos and chinos of the Boston Brahmins. And the self-respect conveyed through the dignity of Sunday best became a weapon wielded by Black Americans in the fight for basic freedoms during events such as the March on Washington in 1963.
[Preppy (or preppie) is a fashion style associated with the alumni of college-preparatory (“prep”) schools in the Northeastern United States. It has its roots in, and substantially overlaps with, the “Ivy League” style of dress (see below), in a more casual, youthful interpretation of Ivy style. Preppy menswear relies on quality tailoring and natural fabrics. Key staples include Oxford cloth button-down shirts, chinos, tailored polo shirts, unlined blazers, and leather loafers or boat shoes (often without socks).
[Preppy style for women centers on timeless staples like pleated skirts, cable-knit sweaters, tailored blazers, and collared shirts, often accessorized with loafers, Mary Jane shoes, headbands, and pearl jewelry. Just as the preppy male attire was a boy’s take on the clothes of the students at Ivy League colleges, the female version was the girl’s take on the dress of students at the Seven Sisters colleges, the women’s counterpart to the Ivies.
[Ivy League style—or “Ivy”—is a timeless menswear aesthetic blending British tailoring with relaxed, sporty American collegiate wear. The style evolved on the campuses of the eight elite Eastern universities dubbed the Ivy League from the 1920s through the 1940s, and became mainstream in the 1950s. Key elements include natural-shoulder blazers, Oxford cloth button-down shirts, flat-front chinos, and leather loafers. It prioritizes casual elegance, quality fabrics (wool, tweed), and a comfortable, lived-in feel.
[Women’s Ivy League style blends tailored menswear elements with smart, collegiate basics. It relies on crisp Oxford shirts, cable-knit sweaters, and trench coats, balanced with pleated midi skirts, loafers, and a refined, earthy color palette. The women’s Ivy style developed on the campuses of the Seven Sisters about ten years after the men’s style began.
[John F. Kennedy [also known as JFK; 1917-63; 35th President of the United States: 1961-63], along with the extended Kennedy family (i.e., “the Kennedy clan”), epitomized everything preppy during its mid-20th-century heyday. JFK’s effortless blend of casual sophistication—polo shirts on the sailboat, chinos at family gatherings, and sharp suits in the Oval Office—set a benchmark for a style that feels as relevant today as it did in the 1960s.
[The Boston Brahmins are members of Boston's elite, wealthy, and educated historic upper class. Descendants of the earliest English colonists are typically considered to be the most representative of the Boston Brahmins. The term, derived from brahmin, the chief priestly caste in the Hindu caste system, refers to White Anglo-Saxon Protestants (WASPs) of old English and Puritan descent who built America’s closest equivalent to an aristocracy. They were known for a style of “quiet luxury” that favored conservative, high-quality attire (such as navy or charcoal suits combined with well-polished vintage leather shoes).]
Not quite two decades later, Martha Stewart [b. 1941; retail businesswoman, writer, and television personality] cooked up a new version of suburban life, repackaging her kitchen in Connecticut as a kind of apple pie paradise and herself as a domestic goddess.
The one thing all of these versions of the American dream have in common, however, is the belief in the power and right of every person to reinvention and optimization in any way available. It was the premise on which Hollywood was built, starting in the Golden Age with the soft focus, idealized and manufactured beauty of stars like as Jean Harlow [1911-37; film actress], Lena Horne [1917-2010; singer, actress, dancer, and civil rights activist] and Greta Garbo [1905-90; Swedish and American film actress], whose fame was its own kind of fortune.
Not to mention the promise inherent in the high-wattage sparkle of disco, where every song and sequin was electrified, as well as the physical perfection dangled by the aerobics age that followed, channeled most effectively by Jane Fonda [b. 1937; actress and activist] in her 1982 VHS workout tape [Jane Fonda’s Workout], which became one of the best-selling home videos of all time.
Reinvention was the basis of the rejection of the old corporate uniform by the social media pioneers of Silicon Valley, who introduced the “zero dress code,” redefining office wear to suggest they were redefining industry, making it accessible to all. By the 2010s, it became the platform on which the Kardashians introduced themselves, becoming the ultimate avatars of the influencer economy in which celebrity through self-modification was an end in itself.
[The Kardashian family, also referred to as the Kardashian-Jenner family, is prominent in the fields of entertainment, reality television, fashion design, and business. Through different ventures, several members of the family are reported to have assets of over $1 billion. From October 2007 through June 2021, they appeared together on the highly popular, albeit controversial, reality television show Keeping Up with the Kardashians. The show’s 14-year run gave and maintained media exposure to each member of the family, allowing them to start and build their individual careers in multiple businesses. (The family has been criticized as being “famous for being famous.”)]
In many ways, Trump’s version of the American dream is simply a throwback to the set dressing and costumes of the former gilded ages, viewed through the lens of televised materialism.
But even as it may seem increasingly stale and commodified, kitschy and tainted, the American Dream continues to endure — rewritten, revived, and reinterpreted by the figures shaping our lives and imaginations.
Because ultimately the look of the American dream is no more static than the dream itself. As Cullen said, it is “most authentically experienced as a struggle to achieve, not a destination.” And it is worn that way, too.
[Vanessa Friedman has been chronicling the relationship of clothing to identity, power, and politics for the New York Times since 2014. She focuses on fashion as an expression of political, social, and cultural identity at a specific moment in time, especially how it is used by those in the public eye to communicate values and influence opinion.
[She looks at how designers translate that into products for all of us on the runway, as well as the evolution of fashion into a part of pop culture. She also examine the way all of that influences the larger business of fashion, one of the world’s biggest industries.
[Prior to joining the Times, Friedman spent 11 years at the Financial Times, five of them in London. She was the FT’s first fashion editor, and the FT was my first all-fashion job.
[Before that, Friedman focused on culture coverage at magazines such as InStyle, The Economist, and The New Yorker. She’s won the Fashion Group International’s Media Award, the Front Page award for fashion writing, and the Fashion/Beauty Monitor award for fashion journalist of the year.
[For “250 Years of Dressing
for the American Dream,” she spoke with historians and museum curators about
the patterns they saw in its seams.]