Men and Style

1. Style is Personal Expression, Distinct from Fashion.

Fashion is industry; style is culture.

Defining style. Style is presented as a holistic aestheticism, an individualistic approach to dressing that reflects one's inner world and worldview, unlike fashion which is seen as trend-driven and for followers. A man of style does things his own way, subtly or overtly, prioritizing timelessness over the latest trends. It's about honoring oneself and demonstrating individuality.

Beyond trends. True style is not about chasing street-style photographers or adhering to industry dictates. It's about cultivating a personal sensibility that may have roots in childhood or inheritance, focusing on ideas, themes, arts, and rituals that constitute culture rather than marketing. The dandy, in the classical sense, is an individualist who dresses for himself and a select few peers.

Subtlety and detail. Often, style is found in the details, the "devil" that distinguishes the individual. It's not about making a spectacle but about an exquisite propriety, a subtle rebellion against vulgarity and triviality. This personal expression is a form of art, approaching life with care and intention in every aspect, including dress.

2. Fathers and Early Influences Shape a Man's Path.

What my father gave me was an appreciation of tailoring, an appreciation of clothes, the recognition that clothes are part of your personal fabric.

Inherited sensibilities. Many men interviewed trace their early interest in clothes and style back to their fathers or grandfathers. Whether through formal dressing habits, specific garments, or a general sense of propriety, paternal figures often provided the initial spark or framework for understanding personal presentation. This influence could be direct or through observation.

Diverse paternal styles. Fathers exhibited a range of styles, from conservative bankers in Brooks Brothers suits to relaxed Hollywood writers, mechanics in chambray shirts, or even those with flamboyant tastes. These diverse examples, whether embraced or rebelled against, formed the foundation upon which sons built their own sartorial identities.

• Banker in suits and rep ties
• Mechanic in work shirts and boots
• Artist in relaxed casual wear
• Vicar in dog collars and tweed ties
• Salesman in sport coats and ties

Lessons beyond clothes. Beyond specific clothing items, fathers often imparted broader lessons about carrying oneself, respecting occasions, and the importance of appearance as a reflection of self. These early lessons, sometimes learned through disagreement or observation, became integral to a man's developing worldview and how he presented himself to the world.

3. Learning Style (and Life) Comes Through Mistakes and Experience.

A life without certain embarrassments has not been fully embraced—that’s why they take your picture at prom.

Embracing missteps. The path to developing personal style is paved with mistakes and moments of embarrassment, particularly during youth. These sartorial misjudgments, whether red suspenders, ill-fitting rented tuxedos, or questionable color combinations, are seen as integral to the learning process. They provide valuable lessons that formal instruction cannot replicate.

Trial and error. Experimentation, even when resulting in failure, is crucial for self-discovery in style. Trying out different looks, like wearing soccer jerseys under a sport coat or sporting clothes far from their intended context, helps men understand what works for them and what doesn't. This process is often driven by youthful exuberance and irrational passion.

• Wearing underpants over pants
• Sporting turquoise shorts with tube socks
• Trying out purple velour shirts
• Wearing a band-collared tuxedo
• Donning leather pants in the early 2000s

Hard-earned wisdom. Ultimately, navigating these awkward phases and learning from them leads to a better understanding of oneself and how to dress with dignity and confidence. The wisdom gained from these experiences, like knowing when to wear a sport coat or never ordering a pink cocktail, is passed down through stories and becomes part of a man's personal history.

4. Understanding and Respecting Dress Codes Shows Awareness.

Unless you are known by one name or have taken your own company public, a dress code is not to be tested lightly.

Rules of the game. Dress codes, while sometimes seen as restrictive, are presented as opportunities to show a sense of occasion and respect for the establishment or event. Adhering to a dress code, rather than trying to subvert it, demonstrates an understanding of social norms and a willingness to participate in a shared tradition. Wearing a house jacket at a formal restaurant is seen as a sartorial failure.

Beyond conformity. While uniforms and strict dress codes in youth might have been met with rebellion, adult understanding recognizes their value in setting a standard and creating a specific atmosphere. Choosing to dress well for an occasion is an act of intention, honoring the house style and elevating the experience for oneself and others. It's about making an impression.

Subtle rebellion. Even within formal constraints, there are ways to express individuality, such as the width of a tie knot or the choice of accessories. However, this expression is most effective when it operates within the established framework, demonstrating mastery of the rules before subtly bending them. The goal is to look sharp and appropriate, not out of place.

5. Classic Garments (Suits, Blazers, Ties, Hats, Shoes) Endure for a Reason.

A well-tailored coat will serve you well most places you go, particularly if you’ve been subpoenaed.

Timeless foundations. Certain pieces of menswear have endured for decades, even centuries, because of their inherent quality, versatility, and ability to flatter the wearer. The suit, the blazer, the tie, the hat, and classic shoes are highlighted as pillars of a gentleman's wardrobe, offering a sense of tradition and reliability in an ever-changing world.

• The suit: A frontier of craftsmanship, built by hand.
• The blazer: Represents classicism and unimpeachable ideals.
• The tie: A declaration of intent, announcing understanding of society.
• The hat: A cultural barometer, asserting one's unique place.
• White shoes: Convey optimism, individuality, and liberation.

Power and meaning. These garments carry cultural weight and convey specific messages. A well-tailored suit suggests adherence to classical style, a blazer offers endless opportunities for pairing, and a tie signals understanding of occasion. Hats reveal personality, and even the choice of shoes, like white bucks or sockless loafers, makes a statement.

Investment in quality. Building a wardrobe around these enduring pieces is seen as a long-term investment in quality over quantity. While the initial cost may be high, these items are meant to last, evolve with the wearer, and provide a sense of confidence and preparedness for various situations, from formal events to unexpected legal summons.

6. Authenticity is a Hard-Earned Pursuit, Not a Trend.

Like pornography, we know authenticity when we see it.

The elusive ideal. Authenticity is presented as a highly valued but often imitated quality in culture and style. It's recognizable, instantly classic, and cannot be bought or easily replicated, despite constant attempts by designers and marketers. This pursuit often leads to friction between those who feel they discovered something first and those who follow.

Beyond the surface. True authenticity is not about adopting a look or trend, like distressed jeans or a specific subculture's style. It's about an internal logic, a singular eccentricity that reflects a lived-in history and self-knowledge. It's earned over time through experience, not acquired overnight.

Resisting the chase. The unending pursuit of what's "next" or "under-the-radar" can be exhausting. Authenticity is less about being ahead of the curve and more about being true to oneself, even as trends catch up or neighborhoods change. It's about having a taste that is uniquely your own, regardless of its popularity or obscurity.

7. Acquired Tastes Reflect a Developing Appreciation for Nuance.

You certainly wanted to give your heart to herring, but herring does not give itself to love so easily.

Evolving palate. Developing acquired tastes, whether for certain foods, music, or styles, is part of personal growth and a journey towards appreciating complication and nuance. What might be initially off-putting or unfamiliar can, over time and with repeated exposure, become a source of deep pleasure and understanding. This applies to everything from herring and natto to specific authors or musical genres.

Beyond first impressions. Some tastes require persistence and a willingness to revisit them, challenging initial resistance. Others might click instantly, like discovering a band or book that feels meant for you at a specific moment. The process is unpredictable and personal.

Trusting intuition. Ultimately, navigating acquired tastes involves deciding when to keep trying and when to trust your initial instinct and move on. It's about expanding your horizons and allowing yourself to be surprised, recognizing that developing a sophisticated palate in any area is an ongoing process of discovery and refinement.

8. Imperfection and Lived-In Details Add Character.

The flaw, in the context of the meticulousness of everything else, was inspired.

Beauty in wear. Perfection in clothing, like brand-new white shoes, is often less interesting than items that show signs of wear and history. A stain, a frayed collar, or thinned elbows tell a story and reflect the wearer's life, adding character and depth that cannot be replicated by artificial distressing. This applies to everything from suits to jeans.

Confidence in flaws. Well-dressed men often embrace these imperfections, understanding that they contribute to a sense of authenticity and ease. Like a chef not apologizing for a slightly deflated soufflé, confidence allows one to carry minor flaws lightly, making them seem intentional or even inspired within the overall presentation.

Earned individuality. True individuality in style is not achieved instantly but develops over time as clothes are lived in and reflect the wearer's journey. This hard-earned individuality, with all its flaws, is more compelling than a manufactured look. It's about being honest about one's history and letting it show.

9. Civilized Drinking and Bars Offer Essential Connection and Refuge.

The most important thing about a bar is that it suggests the better nature of drinking: conviviality, civility, with a lack of inhibition and a basic surge of optimism and solidarity.

More than just drinks. Bars are presented as vital social spaces that offer refuge, connection, and a break from the fast-paced world. The ideal bar fosters conviviality and civility, providing an atmosphere conducive to conversation and shared experience, distinct from places that are loud, themed, or filled with distractions like televisions.

The value of regulars. Becoming a regular at a good bar offers rewards, including an intimate relationship with bartenders who understand human frailty and provide a professional yet personal connection. These relationships are built on trust and mutual respect, often involving generous tipping and an understanding of when one needs a break from the hard stuff.

Finding the right fit. The perfect bar is hard to find, but once discovered, it becomes a reliable haven. Whether a small European hotel bar, a classic New York institution, or a local dive, the right place offers a sense of assurance and allows one to catch up with the world, or escape it, with dignity and good company.

10. Personal Choices, Like Beards or Cash, Define the Man.

A man has a face full of hair, and he rightly wants to share it with the world.

Acts of self-definition. Seemingly small personal choices, such as growing a beard, carrying cash, or selecting a signature scent, are presented as significant expressions of a man's nature and how he defines himself. These choices, whether resisting societal norms or embracing tradition, contribute to his unique identity.

Beyond utility. Carrying cash, for instance, is not just about transaction but about being prepared, liquid, and ready to settle accounts, reflecting a sense of assurance. Similarly, choosing a cologne is about finding an enduring scent that becomes synonymous with one's presence, using sensory power to advantage.

Cultivating identity. Growing a beard is an act of embracing nature, requiring cultivation and resisting external judgments. Like other personal choices, it frames the face but ultimately reveals character, not hides flaws. These individual decisions, from grooming habits to preferred payment methods, contribute to the overall portrait of the man.

11. True Style is an Ongoing Journey of Self-Knowledge.

Ultimately, in the end, we all have to make our own way down the long, rewarding path toward hard-earned individuality, with all its flaws.

Continuous evolution. Developing true style is not a destination but a lifelong process of self-discovery, learning, and refinement. It involves navigating influences, making mistakes, embracing imperfections, and constantly evolving as a person. This journey leads to a hard-earned individuality that is authentic and deeply personal.

Beyond external validation. While external factors like trends, dress codes, and the opinions of others play a role, the core of style lies in self-knowledge and expressing who you are and aspire to be. It's about building a wardrobe and a life that makes sense on your own terms, reflecting your worldview and experiences.

The sum of details. Style is built from the accumulation of small choices and experiences over time – the inherited tie, the worn-in shoes, the preferred bar, the acquired taste. These details, with all their flaws and histories, combine to create a portrait of the man, a unique expression that is both familiar and singular.

Last updated: June 1, 2025