Not every pastime long linked with well-dressed men is truly gentlemanly. From James Bond’s baccarat tables to Don Draper’s decanters, popular culture glamorizes behaviors that can just as easily derail a life as enhance it.
Below, we examine seven classic vices and consider why they tempt us, where they turn dangerous, and how a modern gentleman can indulge (or abstain) without losing his self-respect.
1. Gambling
Risk stirs the human mind, and a courteous evening at the baccarat table can offer excitement, camaraderie, and—occasionally—a pleasant monetary surprise. The danger lies in chasing losses or viewing the casino as a means to quickly generate income.
RISK WITH RESTRAINT
Treat Winnings as a Gift, Not a Goal
Decide your entertainment budget before you step inside, treat any winnings as a gift, and walk away when that stake is gone.
In short: wager for fun, never for salvation.
2. Smoking
A well-made cigar engages all the senses and fosters a sense of community in cigar lounges. Yet tobacco carries undeniable health costs, even in moderation. Enjoying a rare celebratory smoke is a personal choice; make it an informed one and respect those who prefer fresh air.
“Boredom is therefore a vital problem for the moralist, since at least half the sins of mankind are caused by the fear of it.”
Bertrand Russell, The Conquest of Happiness
3. Drinking
Shared drinks build fellowship and can be a genuine connoisseur’s pursuit. Still, alcohol’s risks—from impaired judgment to long-term health effects—rise sharply with each extra glass. Know your limits, alternate with water, arrange safe transport, and remember that many gentlemen thrive without drinking at all.
4. Gourmandism
Fine food enriches life and, for many, it sparks a rewarding journey into cooking. The modern world, however, makes overeating easy and maintaining a nutritional balance harder. Savor exceptional meals, but pair them with mindful portions and regular activity: your wardrobe (and well-being) will thank you.
Confused by table etiquette?
5. Sartorialism
Appreciating quality tailoring is central to classic style, yet it can sour into snobbery. Dress to please yourself, share knowledge generously, and NEVER belittle others for different tastes or budgets. Confidence in one’s clothes should breed inclusivity, not gatekeeping.
Is today’s outfit an example of sinful sartorialism? Let’s find out.
For today’s outfit, I am wearing a sport coat in a pretty loud Prince of Wales pattern, and it has blue windowpane to it. I paired the jacket with a lighter denim shirt; on the bottom, I am wearing charcoal trousers, and on my feet, I have brown Jay Butler loafers.
My pocket square is in a lighter blue tone—it goes well with the jacket’s windowpane and also has a bandana graphic, which mixes in another pattern to the outfit overall. On my wrist, I am wearing a Timex automatic with a blue band, and for my scent today, I’m wearing Azuro from the Roberto Ugolini collection.
For the fragrance, as well as other men’s wear accessories, make sure you check out the Fort Belvedere shop.
6. Epicureanism
Whether crystal stemware or vintage motorcars, a love of excellence elevates daily life. Problems arise when possessions become proxies for self-worth or lead to unethical behavior. Cultivate admiration for craftsmanship, but remember that relationships and character provide deeper, longer-lasting rewards.
Want refined etiquette tips?
7. Philandering
Romantic adventure can be exhilarating, provided everyone involved is informed, consenting, and treated with respect. Deception, objectification, or casual disregard for partners turns pleasure into harm.
Honesty, clear intentions, and empathy distinguish a gentleman from a rake.
Learn 15 Things Only Gents Do…
Final Thoughts
Historically, wealth and status insulated many “gentlemen” from the fallout of their excesses. In the modern world, real refinement rests on self-control and consideration for others.
Engage—or abstain—from these vices by knowing your limits, valuing transparency, and refusing to let indulgence eclipse integrity. That balance, not the vice itself, is what keeps a pastime gentlemanly.
Frequently Asked Questions
Is drinking or smoking gentlemanly?
These activities aren’t inherently gentlemanly, but certainly can be enjoyed by gentlemen. The important thing is to practice moderation and know your limits.
Is it bad to value clothing?
Having an interest in menswear can lead to a fulfilling hobby that helps you to build your self-confidence, but it’s important to remember it’s not the most important thing in life, and not to engage in snobbery over it.
Is smoking classy?
While there are some strong associations with cigars & wealth, smoking isn’t inherently good or bad. It depends on the occasion, and excess smoking or engaging in excessively damaging behavior isn’t classy, no matter the vice.
Is it bad to want nice things?
There’s nothing wrong with appreciating the finer things in life, but excess greed and being ruthless in the pursuit of them can have damaging consequences.
What’s the deadliest sin?
The deadliest sin is the one you engage with to an excessive extent. Anything not in moderation can be dangerous.
Cultivating Courtesy: Essential Skills for the Modern Man
Apologize Like a Gentleman
Social Etiquette for Saying “Sorry”
A step-by-step primer on issuing sincere, effective apologies that restore respect and goodwill.
The Art of Charm
How To Have A Great Conversation
Simple techniques to start, steer, and sustain engaging dialogue—anytime, anywhere.
Online Etiquette 101
How to Be a Gentleman Online
Learn the do’s, don’ts, and timeless courtesies that keep your digital presence civil and classy.
Nice work.
Informative, reflective and recalling.
Tks.
Ron
Thank you, Ron – glad to hear you enjoyed the video.
Hi guys, my interest in Italian Silk Suits lead me to your’ web page and as much as I would never choose to be known as a Gentleman; you might as well call me Sir, which I dread, my ambition in learning more about Italian Silk Suits drives me onward.
Here in Scotland there are plenty of Tweed garments to choose from and it might be nice to wear a Tweed Suit in the USA next time I appear over I love the look of Italian Neopolitan Suits. I often see the silk fabric with fuzzy parts on it possibly from frequent wear and would ask your’ expert opinion as to how to avoid these little moth balls that are too often seen on Silk. Guys, how can the spoiling of silk be avoided?