Chapter 1
The Sartorial Journey: Style as a Reflection of Character
Men and style-two words that conjure images ranging from the impeccably tailored suits of Savile Row to the effortless cool of James Dean in a white t-shirt. But this isn't merely about fashion; it's about the holistic aestheticism that gives reason for living. The true dandy isn't someone who makes spectacles but embodies subtle distinction, dressing to honor himself and demonstrating the superiority of the timeless over the latest trend. As Gay Talese-whose father trained with Antonio Cristiani from a five-generation Italian tailoring dynasty-reminds us, "Unless you have a sense of self, you're not going to wear clothes with any pride, because the clothes are wearing you." The book has earned praise from style icons like Tom Ford and Ralph Lauren, who recognize its unique ability to capture how clothing choices reflect our inner lives. With its blend of personal anecdotes, expert interviews, and cultural observations, it offers a roadmap for navigating the complex terrain of masculine identity through the lens of personal style.
Chapter 2
The Evolution of a Man's Style: From Childhood Obsessions to Adult Refinement
Our relationship with clothing begins in childhood, often with peculiar fixations that make little sense in retrospect. The author recalls his own youthful obsessions - red suspenders at age twelve, matching his turquoise shorts to his beloved Miami Dolphins, and coveting Michael J. Fox's two-tone jean jacket from Back to the Future. These early attachments form without the benefit of perspective, driven by pure passion rather than aesthetic reasoning. Such early style choices often reflect a child's heroes, interests, and desire to belong, creating lasting memories that influence future fashion sensibilities.
Many men interviewed share similar stories of childhood style experiments, revealing how early preferences shape lifelong relationships with clothing. Michael Williams was "extraordinarily particular," dragging his mother from store to store in search of the perfect outfit, spending hours debating the merits of different sneaker styles and obsessing over specific clothing details that most adults would overlook. Alexander Gilkes secretly changed whatever outfits his mother laid out for him, developing an early sense of autonomy through his wardrobe choices. Some had early style influences from their fathers - Michael Hill's father was a tie maker who created pieces for Princes William and Harry, introducing him to the artistry of fine menswear, while Hirofumi Kurino drew inspiration from western movies, particularly admiring the rugged elegance of cowboys and their distinctive dress codes.
School uniforms provided another formative clothing experience, teaching both conformity and the subtle art of rebellion. Nick Sullivan recalls strict gray suit requirements at his secondary school, where even minor deviations could result in detention. Glenn O'Brien remembers Jesuit high school ties, with students rebelliously wearing turtlenecks over them until "Jesuits would come up and pull your turtleneck down to see if you were in compliance." This cat-and-mouse game of rule-breaking became an early lesson in style subversion. Alex Bilmes describes personalizing his uniform by safety-pinning seams and manipulating tie lengths as "a way to express a certain amount of subversion," demonstrating how even within strict dress codes, personal style finds a way to emerge.
College represents a critical style evolution, marked by experimentation and identity formation. This period often sees dramatic shifts as young men discover themselves away from parental influence. Jay Fielden describes his "hardcore Ralph Lauren" phase, working at a Polo Shop primarily for the employee discount, immersing himself in preppy Americana. Duncan Hannah embraced Bowie-inspired fashion at rural Bard College, wearing "huge black fedoras and... women's clothes" including "Joan Crawford overcoats," much to his father's dismay - a bold statement of independence through clothing. Musical influences heavily shaped college style, with Hirofumi Kurino moving from long-haired Vietnam War protester to Bryan Ferry-inspired traditionalist, realizing "I could keep a rebellious attitude and dress traditionally." These college years often mark the beginning of a more conscious approach to personal style, where men start to understand how clothing can express both individuality and group belonging.
The transition from youthful experimentation to adult refinement rarely follows a straight path. Many men describe cycles of discovery, rebellion, and eventual synthesis - finding ways to incorporate their various style influences into a coherent personal aesthetic. This evolution continues throughout life, with early experiences providing the foundation for more sophisticated style choices in adulthood.
Chapter 3
Fathers and Sons: The Inheritance of Style
The relationship between fathers and sons often finds expression through clothing-whether in emulation, rebellion, or some complex combination of both. The author recalls meaningful exchanges with his father around culture and style, including receiving a copy of The Great Gatsby with its opening advice: "Whenever you feel like criticizing any one just remember that all the people in this world haven't had the advantages that you've had." This moment crystallized his recognition of the cultural and stylistic advantages his father had passed down.
Weekly tennis matches with his father revealed contrasting approaches-his father played a direct style while the author relied on counterpunching. Even their tennis equipment told a story: his father carried his racket in a simple canvas carpenter bag while the author used an oversized professional bag that was "basically empty"-a telling contrast in their approaches to style.
Interviews reveal how fathers' sartorial choices influenced their sons. Josh Peskowitz recalls stealing his father's Polo sweaters, Frank Muytjens remembers his salesman father always in white shirts and ties, and Michael Hainey describes his father's glamorous newspaper days with dark suits and thin ties. Randy Goldberg's father maintained an unusual formal-casual hybrid-dress shirts tucked into sweatpants with leather slippers.
Fathers also imparted style rules to their sons. Andy Spade recalls his father taking him shopping, buying him "the right shirt and the right tie" and giving all his children silver monogrammed belt buckles. Tom Schiller learned the military tuck for shirts from his army veteran father, while Duncan Hannah's father was "a real stickler for propriety" with rules about belts, not mixing brown and black, and wearing appropriate shoes. Euan Rellie's British father advised against matching clothes: "Americans like to match their clothes-you're British, remember always to clash your clothes."
The transmission of style extends to physical objects as well, with men cherishing inherited items: Eric Dayton's grandfather's naval officer pins, Jay Batlle's father's pocket watch and vest, Nick Wooster's father's watch, Russell Kelly's grandfather's lighter, Chris Brown's father's Stetson hat, JP Williams's father's dog tags, and Brian Awitan's father's watch.
Chapter 4
The Pursuit of Authenticity in an Age of Imitation
Authenticity remains the elusive holy grail of style - instantly recognizable yet impossible to purchase outright. It manages to be simultaneously new yet familiar, imitated yet unique, and "instantly classic." This paradoxical quality creates endless friction between early adopters and those who follow, with pride coming from being first: living in neighborhoods before gentrification takes hold, discovering artists before mainstream fame embraces them, eating at hole-in-the-wall restaurants before they acquire liquor licenses and Michelin stars.
The pursuit of authenticity has become increasingly complex in our digital age. There's always someone newer, hungrier, and trying harder who will eventually discover your secret spots, frequent your hidden gems, and move into your once-undiscovered neighborhood. The internet has dramatically accelerated this cycle, making "the exotic familiar faster" and allowing anyone with a smartphone to access what was once obscure. Social media particularly has transformed local secrets into global destinations overnight, whether it's a tucked-away jazz club in New Orleans or a family-run ramen shop in Tokyo.
The case for imperfection connects deeply to this pursuit of authenticity, offering a counterpoint to mass-produced perfection. White shoes perfectly exemplify this principle - they begin pristine and uniform but achieve true character only after acquiring the stains and marks that tell your unique story. The transformation happens gradually as they collect memories: your trip to New Orleans' French Quarter, the unexpected summer storm in Chicago, the grass stain from a spontaneous lawn bowling escapade in Central Park. We're naturally drawn to things with honest history and earned character: "The boxer's broken nose, flawed heroes, the singer's aging voice that carries decades of experience."
Fred Astaire famously threw his new suits against walls to break in their newness, inherently understanding that clothes should reflect their wearer's life, not their maker's vision. This philosophy extends beyond fashion - the well-dressed man's frayed collar, the chef who never apologizes for kitchen mishaps, the vintage leather bag bearing scuffs from countless travels - all share this quiet confidence in imperfection. There's a delicate balance between perfectionism and cultivated taste, with true style emerging through personal experience rather than manufactured shortcuts. As one vintage dealer noted, "A pair of pre-distressed jeans isn't going to do the trick; you're going to have to break them in yourself." This authentic wear becomes a physical memoir of experiences lived, rather than a simulation of character purchased off the rack.
The most compelling spaces, objects, and styles often bear witness to real lives lived - the worn wooden bar top in a neighborhood pub, a grandfather's well-used tools, or a decades-old family recipe book complete with food stains and margin notes. These items carry what the Japanese call wabi-sabi - the beauty of imperfection and the patina of use - making them impossible to replicate through artificial means.
Chapter 5
The Elements of Style: From Head to Toe
The hat functions as a cultural barometer, revealing profession, occasion, and era. Today's hat-wearer takes a deliberate stand against conformity-there is no neutral hat. The fedora carries Rat Pack undertones, the bowler evokes Chaplin's playful performance, while the trilby signals a man who "walks alone." Kennedy may have banished hats for generations, but they're returning as men rediscover traditional garments. A proper hat should serve your personality, making you look more yourself, not less.
The custom suit represents the last frontier of superior craftsmanship, built entirely by hand. Though expensive-something you might smuggle into your closet under cover of darkness-the investment supports tailors who've apprenticed for years, not advertising campaigns for duty-free cologne. The well-dressed man advocates fewer, better options, focusing on timeless pieces that could have been worn a decade ago and will remain relevant a decade hence.
The blazer embodies timeless classicism while flattering the wearer-as essential to a man's wardrobe as a properly made martini is to his cocktail repertoire. Originally red and worn by Cambridge rowers in 1825, blazers evolved to indicate club membership with various colors, stripes, and crests. As Jonathan Ames puts it, "If sport coats were inner organs, the blue blazer would be the lungs-absolutely essential."
The tie maintains cultural power even in its absence-a declaration of intent that announces your understanding of society. When authority figures like coach Jason Kidd forego ties, it signals another step down the path of informality. While we're past the era when ties were mandatory for all men, deliberately choosing when to wear one shows proper consideration. Boys wear ties against their will; men understand occasion and rise to it.
Men's tie collections vary dramatically, from modest collections to impressive hoards. JP Williams owns "Thirty-three ties, four bow ties" while Jay Batlle knows "each one personally." Collections range from Dan Rookwood's precise "Fifty-three" to Nick Sullivan's honest "About sixty. I wear two." The largest collections include Andy Spade's "One hundred and six," Mark McNairy's blunt "A shitload," Nick Wooster's "After a massive culling, 137," and Glenn O'Brien's precisely counted "179 ties."
The scarf does more than provide warmth-it's an expression of style and personality. The author recalls his student days in Paris, observing Parisians "draped in a brilliant array of scarves. Brightly colored, nonchalantly wrapped, inevitably elegant." A perfect scarf becomes part of one's identity: "you feel oddly naked without it."
The pocket square transforms a sport coat from ordinary to distinguished. "If a suit represents your adherence to classical style, then the pocket square is a chance to express your individuality." The author suggests starting with the "Don Draper approach-straight and white as an index card," which pairs well with "a narrow-lapel coat, an ice-cold martini, and a worldview that takes no prisoners."
Chapter 6
Rituals and Indulgences: The Gentleman's Life Beyond Clothing
A man's style extends beyond his wardrobe to encompass his rituals, habits, and indulgences. The author examines the modern trend of men going sockless, even in formal settings. What began as "a relaxed summertime tradition" has migrated to business attire, influenced by designer Thom Browne's shortened trousers that "may appear slightly shrunken on anybody not fully indoctrinated in his sensibility." Ironically, this casual look now "signifies a sort of formal rigor; to look offhand and relaxed now takes considerable strategizing."
Formal dining maintains its place in a well-rounded life. While the evolution of New York dining has brought many positive changes, there remains a place for classical elegance-somewhere hushed where one can slide into a banquette, enjoy ironed linen, weighty silver knives, and service from a tuxedoed professional rather than tattooed arms. The incongruity of a four-hour lunch in today's world makes it more transcendent-a withdrawal from news cycles and social media hum into sensory pleasure and intimate company.
Bars have survived Prohibition, gentrification, and amplification because people want to drink in the company of others. The best bars suggest drinking's better nature: conviviality, civility, optimism and solidarity-like the first crisp sip of champagne rather than the last slug of tepid beer. Becoming a regular brings rewards, though confronting how much time you've spent there can be sobering. Bartenders know as much about you as your analyst or accountant, understanding human frailty while maintaining professional but not superficial relationships.
The beer you grow up with creates associations so strong they overwhelm objective judgment, leading to fierce loyalty when someone criticizes your regional favorite. For the author, summers in Wisconsin meant Leinenkugel's from Chippewa Falls, a brewery dating to 1867 that proudly claimed to be "brewed by 73 people who care." Men generally want consistency in their beer, Scotch, and clothes-not endless novelty.
Old Spice evokes powerful memories regardless of whether you've worn it-its scent is embedded in our collective consciousness. Originally introduced in 1934 as an exotic escape with nautical aspirations (the porcelain bottle designed to resemble a buoy), it represented adventure for one generation before becoming the reassuring scent of fathers and grandfathers for the next. A man should find an enduring scent and stick with it-you shouldn't smell like a certain scent; other men wearing it should smell like you.
Chapter 7
The Modern Man's Interior Life
The modern man's living space should transcend the stereotypical "man cave" with its sports-locked TV and takeout lifestyle. A thoughtfully curated home environment reflects personal growth and emotional intelligence while creating a sanctuary for both solitude and social connection. Several strategic upgrades can transform a basic bachelor pad into a sophisticated personal retreat that nurtures both body and spirit.
Start by downsizing your television - your life shouldn't revolve around a screen. Consider mounting it discreetly or housing it in an elegant cabinet that closes. Invest in quality rugs to warm wooden floors, focusing on natural fibers like wool or silk that age gracefully. Find at least one inviting reading chair that beckons you to sit - perhaps a classic leather wingback or a modern lounge piece that serves as both functional furniture and sculptural element.
Books are essential markers of intellectual life - carefully chosen anthologies, compelling biographies, exhibition catalogs, and literature that reflects your passions and journey. Display them thoughtfully on well-built shelves, allowing them to create a personal history of your experiences and interests. Quality lighting transforms any space: replace harsh overhead fixtures with layered lighting including floor lamps, table lamps, and strategic task lighting. Warm, dimmable bulbs and carefully placed candles create ambiance while flattering both rooms and faces.
College living spaces often reveal profound insights about emerging adult identities. Stephen Coates transformed his twentieth-floor council flat into a minimalist refuge for "brokenhearted men," stripping away dated wallpaper to create clean white walls. There, he and his roommate spent evenings analyzing each other's dreams using Jungian principles, their sparse furnishings encouraging deep conversation rather than distraction. Frank Muytjens, who later became a notable designer, decorated his art school room with carefully curated Pop Art posters and daringly threw red paint on one wall - a rebellious act that cost him his deposit but expressed his emerging creative identity.
Some students embraced meaningful austerity, like Walter Kirn who constructed his college space around towering stacks of books used as architectural elements - "pillars with something on top of them." This approach transformed necessity into aesthetic intention, creating a space that reflected both material constraints and intellectual aspirations. Even in modest spaces, thoughtful curation of objects and intentional design choices can create environments that support personal growth and authentic self-expression.
Chapter 8
The Wisdom of Experience: Style as Character Development
A good beard suggests comfort with oneself and achievements-perhaps tenure, a genius grant, or seafaring accomplishment. The bearded man joins a brotherhood connected to Tolstoy, Matisse, and Melville, though growing facial hair inevitably involves heated discussions with loved ones who may not appreciate the "bear emerging from hibernation" aesthetic. The wise bearded man keeps his facial growth well-maintained, using proper grooming to convey an easy sense of formality-a cultural victory against long odds. His beard frames his face without defining him, revealing character rather than hiding flaws.
Acquired tastes are curious considerations, whether in dining, music, clothing, or film. Some foods become appreciated over time-coffee, mushrooms, squid, whiskey-evolving from resistance to pleasure as we develop appreciation for complication and nuance. The challenge lies in knowing when to trust first instincts versus persevering. Sometimes conversion happens by chance-like visiting friends who serve aged rum in summer. Initially rough, soon you're buying it by the case.
The author has begun noticing gray hairs in his beard-not just a light dusting but a determined blizzard that won't retreat. Rather than panicking or reaching for dye, he initially welcomed this development as an easy path to appearing distinguished without actually accomplishing anything distinguished. His appreciation for aging runs deep-he admires direct old men who fish, wear tweed, take naps, and flirt with waitresses. Yet after a few weeks of self-satisfaction, the novelty wore off. The challenge is recognizing change while living through it-you typically identify life phases only after they've ended. In truth, he prefers the abstract idea of aging to its reality-the lower back pain, reduced alcohol tolerance, and wrinkles.
Fishing is a curious pursuit where you repeatedly set yourself up for failure, though the embarrassment comes in different forms. Success is so rare that without photographic evidence, no one will believe you. Yet anglers remain improbable optimists, hoping against hope that this time will be different. The remarkable thing about fishing is how it perpetually makes you feel like a novice. The more you know, the more you realize you have to learn. Yet despite endless disappointment, there's always another chance-which is why we always make one more cast.
Chapter 9
Style as a Lifelong Conversation
The book concludes with an intimate and revealing conversation between the author and his father, exploring how personal style evolves across generations, circumstances, and life experiences. The elder Coggins shares a detailed chronicle of his style journey, beginning with an ill-fated crew cut in Greece around 1958 - a decision he describes as "a terrible mistake" that nonetheless defined his early aesthetic choices. Throughout high school in Virginia's traditionally formal educational environment, he adhered to strict dress codes, wearing letter sweaters paired with ties on game days, embodying the preppy East Coast aesthetic that would later earn him the nickname "Jim Beam."
His college years marked a dramatic transformation in personal style. The shift from East Coast formality to what he terms a more "bohemian" sensibility wasn't merely a change of clothes - it represented a broader evolution in identity and self-expression. His wardrobe expanded to include jean jackets, army surplus wear, and other counter-cultural elements that reflected the social movements of the era. This transformation illustrates how style often mirrors broader societal changes and personal growth.
The dialogue then moves to the author's own style journey, particularly his childhood resistance to the blue blazers his father religiously purchased every two years - a tradition that, while initially met with reluctance, eventually fostered an appreciation for formal dressing. A pivotal moment emerges in their discussion of the author's prom attire: a bold combination of a tuxedo jacket paired with jeans. This choice, encouraged by his father rather than discouraged, represented a significant "turning point" toward what they now recognize as "more serious nattiness" - a moment where personal style began to transcend conventional boundaries.
Their shared memories of European travels in their brown 1970 Triumph GT6 add another layer to their style narrative. These adventures not only strengthened their father-son bond but also exposed them to diverse fashion influences and cultural perspectives that would shape their sartorial sensibilities for years to come. The car itself becomes a symbol of their shared journey through style and life.
This multi-generational conversation illuminates the book's central thesis: style transcends mere clothing choices to become a form of personal expression and character development. It's an ongoing dialogue - with ourselves, our heritage, and our aspirations - about identity and authenticity. The truly well-dressed don't simply follow trends; they create their own sartorial universe with internal logic and controlled anarchy, establishing new rules of possibility and expression. These individuals successfully navigate and often defy the endless stream of cultural branding, maintaining agency over how they're perceived while understanding a fundamental truth: authentic style serves to reveal rather than conceal personality. Their choices in dress become a carefully curated expression of individual character, values, and life experiences.
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