The New Playboy’s Handbook / Chapter Six
by Pier Francesco Grasselli
🕴️ Elegance and Self-Care: A Playboy’s Calling Card
They say clothes don’t make the man, but for a playboy, appearance is essential. This isn’t about superficiality; it’s about understanding a simple and universal principle: first impressions matter, and they are inevitably aesthetic. In the game of seduction, elegance and self-care are aspects that must never be neglected. It’s not enough to be brilliant, funny, or confident—you also need to look your best, because a first glance can be decisive.
Elegance is much more than just a nice outfit. It’s about a proud posture, a composed way of moving and communicating with grace. Gianni Agnelli is the perfect example. His style—the slightly loosened tie, the watch worn over his shirt cuff—was an unmistakable expression of his unique personality. Agnelli’s elegance embodied the essence of sprezzatura, the refined, effortless nonchalance of someone who is supremely self-assured.
It’s the attitude of superior sophistication, with a charming air of spontaneity which is the hallmark of a man who knows well that he embodies the very best humanity has to offer.
Elegance doesn’t necessarily mean wearing elaborate or expensive clothing; it’s about choosing garments that flatter your body and reflect your personal style. For a playboy, this means caring for his appearance without blindly following fashion trends and without losing his authenticity.
You don’t need a runway-ready wardrobe—let me repeat that—and it’s wise to avoid overly trendy items. A few carefully chosen, high-quality pieces can make all the difference. Often, a pair of well-made jeans, a crisply ironed shirt, or a polo shirt is enough. There’s something especially attractive about a well-fitted shirt. They convey a sense of order, reliability, and masculinity that women find highly appealing. The polo shirt, on the other hand, is ideal for more casual situations. It gives off a sporty yet polished vibe, evoking the image of an active, practical, and confident man.
🎪 Chronicles of the Style Apocalypse
We are living in the era of sloppiness—where jeans with rolled cuffs above bare ankles are considered “trendy,” not to mention cheeky shorts and accessories that seem straight out of a trashy movie. It’s the era of electric kick scooters invading cities like some futuristic, kitsch army. So, it’s hardly surprising to see stunningly dressed women with impeccable outfits, stiletto heels, fashionable makeup, and hairstyles, accompanied by guys who look like teenagers on holiday: hoodies, sneakers, faded jeans, and, to top it all off, a fanny pack slung around their waist.
In this jungle of aesthetic negligence, the playboy shines like a beacon in the night, standing out as an ambassador of style and good taste.
👔👖🧥 The Playboy’s Wardrobe
Dressing well is not just about aesthetics; it’s an act of respect—for both yourself and others. A playboy is a gentleman who knows how to navigate any setting with ease, whether it’s a marchesa’s salon or a tropical beach. He understands the rules of elegance, respects them, and reinvents them effortlessly. His wardrobe is a carefully curated arsenal, ready to tackle any social or romantic challenge. Let’s explore the key pillars of this philosophy.
🕴️ The Suit
The men’s suit is a timeless classic and works wonders. It’s no coincidence that Richard Gere in American Gigolo is remembered for his perfectly tailored Armani suits. However, take note: a suit will make you look your best only if you know how to wear it with nonchalance. This applies to all outfits and occasions—the right clothing should feel like a second skin, in which, above all, you are comfortable.
🤵 Tuxedo and Tailcoat: The Armor of Elegance
Tuxedo: Ah, the timeless allure of the tuxedo! The tux is the king of formal elegance, perfect for gala evenings and exclusive cocktail events. Wearing one gives you an aura of authority. But beware: a tuxedo must be treated with the respect it deserves. Avoid plastic-button shirts at all costs. The jacket should be single-breasted, the black bow tie hand-tied, and the shirt white with a pleated front. Never wear a tuxedo before 6:00 PM—it is, after all, the quintessential evening attire.
The Tailcoat: If the tuxedo is the king, the tailcoat is the emperor. This regal outfit is reserved for the most formal occasions, such as official ceremonies, embassy balls, and high-profile weddings. The jacket is short in the front and longer in the back, paired with a white vest. Patent leather shoes are mandatory. Remember, a poorly worn tailcoat is worse than ripped jeans.
Modern Occasions: In less formal but still exclusive settings, the tuxedo can be modernized with personal style touches. A tuxedo jacket paired with a black shirt and dark slim-fit jeans creates a bold yet respectful look.
👔 The Tie Knot: The Art of Details
Let’s be clear: a poorly tied tie knot is like a wrong note in a symphony. A playboy knows his tie knots as well as a sommelier knows his wines.
The Windsor knot, wide and symmetrical, is ideal. For a more relaxed look, the Four-in-Hand is perfect: slightly asymmetrical, but full of character.
The real magic lies in the balance between the tie and the collar. Avoid loud colors or overly wide ties that make you look like a parody of the 1980s. A slim tie, perhaps in matte silk, pairs perfectly with a slim-fit suit to give your look a modern touch.
🧥 The Jacket: The Unifying Element
It doesn’t matter whether you’re wearing jeans or tailored trousers—the jacket rules the look. Want to pair a tuxedo jacket with a turtleneck? Great choice, as long as the fabric speaks of luxury: wool, silk, or cashmere.
Color: Black, midnight blue, and dark gray are timeless classics that never fail. But don’t underestimate the power of a cream or olive-green blazer for daytime events like brunches or receptions. Brown (or “marron,” if you’re feeling fancy) is the intellectual’s color, the one writers, poets, and philosophers wear with existentialist flair, often paired with a distant gaze and a battered notebook. But on a playboy, it comes with a dangerous side effect: it adds ten years and a degree in philosophy, potentially dimming the seductive allure you’re trying to project.
The Fabric: Cool wool is versatile and refined. Linen, with its natural tendency to wrinkle, should be worn with nonchalance—no stress over creases, please. Flannel, on the other hand, screams countryside and weekends with your Setter: it’s warm, yes, but strictly banned from the playboy wardrobe.
Velvet can be a formidable ally—provided you strike the delicate balance between “left-wing intellectual” and “19th-century dandy.” Smooth velvet, especially in black or midnight blue, has a certain decadent charm. But corduroy, like the color marron, is reserved for intellectuals: disillusioned writers, retired professors, and chain-smoking poets.
Silk is pure epidermal privilege—it glides over the skin with grace and instantly evokes luxury, but it must be used wisely. Too much silk, and you risk looking like a Monaco casino baron. Use it intelligently: a black silk shirt, for example, can cast a spell over a candlelit dinner.
As for modern stretch fabrics—yes, they exist, and yes, they’re worth considering. In shirts, a touch of elastane or next-generation technical fibers can spare you the hassle of ironing—as long as they don’t feel like plastic. The rule is simple: they should neither shine nor make suspicious rustling sounds when you walk or sit down. If the fabric feels like discount polyester or looks like an IKEA sofa, walk away.
👖 Jeans: When and How
Jeans are acceptable only when used wisely. Paired with a sports jacket, a crisp white shirt, and loafers, they can be incredibly chic. Say no to ripped jeans, cuffs, and faded fabrics—unless you want to look like the hipster barista from your neighborhood.
📌 The Rules of Casual Wear
For leisure time, a playboy opts for relaxed yet polished looks. Casual should never mean sloppy.
👕👖 Piqué polo with chino pants:
As we have already said, women love polo shirts because they give men a structured, practical, and reassuring appearance. It’s better to pair them with lightweight cotton-based trousers rather than jeans.
🧶 Light sweaters:
Merino wool sweaters matched with slim-fit trousers work beautifully.
🕺 Creative combinations:
Sometimes, a jacket can be combined with a cashmere turtleneck. With dark jeans and leather loafers, you’re ready for an informal dinner at a luxury restaurant.
👞 Shoes: The Foundation of Elegance
Never underestimate your shoes—they are one of the first things women notice. You could look impeccable from head to neck, but if your shoes are wrong, you’re done. Polished black Oxfords are your ticket to formal events, but easy on the shine: you’re not meant to check your hair in them. Brown ones, on the other hand, are fine for the office—or the countryside.
For a more relaxed look, opt for suede loafers, which suggest luxury with ease, without appearing pretentious.
Sneakers are not recommended. A playboy only wears them at home, for sports, or as part of a high-end streetwear ensemble. Always avoid shabby sneakers, even at home. You never know when the woman you’re seeing might show up unexpectedly. As it is written in the Gospel: “Therefore watch out, you do not know the day or the hour.”
👑 Praise Be to the Loafer
For a playboy, the loafer is the ultimate shoe. It’s the emblem of effortless charm—the symbol of relaxed elegance. In a world where most men struggle with laces and buckles, the playboy simply slips into a pair of loafers… and conquers the world in a single step.
Worn by Gianni Agnelli with pinstripe suits, and by Giancarlo Giannini in those iconic ‘70s Italian auteur films, the loafer has always been the shoe of those who have mastered the art of living.
Comfortable yet refined, it was made to move confidently through drawing rooms, hotel bars, and yacht decks alike. It pairs well with jeans, tailored trousers, or even a suit—as long as it’s worn with that bold confidence that separates those who imitate style… from those who set it.
The suede loafer is a caress for both the eye and the foot. Soft and sensual, it’s perfect for sunny days and Amalfi weekends—where style should be relaxed, but never casual. The tasseled loafer, on the other hand, is just cheeky enough: ironic, with a hint of dandy flair. A dove-grey suede loafer is like a good flirt. And let’s be clear—the loafer gives its very best with a bare ankle, because true style begins where the sock ends.
Glossy leather ones? Personally, I find them a little stiff—but in winter, with a fine sock, they can still hold their own. The point is: the loafer is the one shoe you can wear in absolutely any color. It lifts your look, adds energy. So—long live color, especially in summer! From mustard yellow to sea green, anything goes… Say goodbye to boring shoes!
🎖️ Accessories: The Finishing Touch
Accessories are a playboy’s signature. But be cautious—avoid overdoing it and looking like a Christmas tree.
⌚ Watch:
Nowadays, with cell phones always in our pockets, a watch isn’t so much for telling time—it’s a status symbol. It should be classic and never oversized. A Rolex Submariner or a Patek Philippe is always a solid choice if you can afford one, but there are plenty of more affordable and equally elegant options. Forget about Internet-connected smartwatches buzzing 24/7—nothing screams “digital dependency” louder than a wrist that vibrates with every notification. Not to mention, we have good reasons to suspect they’re not that great for your health…
🧿 Cufflinks:
Preferably discreet, in gold or silver. A touch of humor is welcome, but they should never be tacky.
🕶️ Sunglasses:
Always high quality, such as Ray-Ban Aviators or Persol. Never wear them indoors or when the sun is hidden or has set—you’ll look like a fool!
👖 Belt:
Your belt should, if possible, match your shoes: black with black shoes, brown with brown ones. Don’t be afraid of looking gay—be afraid of looking like you got dressed in the dark!
Don’t overdo it with the Mr. T-style chains, or the thick gold ones à la Maradona. The kind of elegance that really seduces is discreet—it doesn’t need to shout “Money” from the rooftops.
And for the love of God—even though I probably don’t need to say this—ditch the five smartphones and the blinged-out tracksuit that shouts “wannabe rapper on a budget”.
Yeah, I know… these days there’s always some babe who melts in front of this pitiful kind of branded meathead—or wannabe gangster, if you will.
But let’s be clear: that’s not the kind of woman a real playboy is after. He goes for quality women, not the ones who trade brains for a Louis Vuitton keychain.
Style isn’t about showing off. It’s about balance. It’s the silence of a ten-thousand-euro watch hidden beneath a cuff. It’s the cut of the jacket—not the logo on the hoodie.
It’s the look that says “I’ve got this”, not the zircon-studded bracelet screaming “Look at me”!
✨ Artists and Attire: Freedom with Style
There is an unwritten rule that grants artists a greater flexibility in their look. However, this is not a license for chaos, maybe more like a “pass” for an unconventional elegance—an opportunity to express creativity through clothing, provided it fits the context.
For instance, at a theater premiere or formal event, even artists should adhere to a certain level of elegance while still keeping their unique touch. A painter at a vernissage might wear a bold velvet jacket or a flamboyant scarf without breaking etiquette. This visual language enhances the overall picture rather than clashing with it.
However, this freedom doesn’t exempt artists from good taste. Eccentricity doesn’t mean sloppiness or tackiness. If a black-tie dress code is required, it applies even to the most rebellious poet—who might, however, opt for a red silk bow tie instead of the classic black one.
🏌️♂️ Old Money, Preppy, and Ivy League: The Elegance of the Born Winners
There are those who try to look rich. And then there are those who are rich. The difference? Style.
Real style doesn’t shout. It doesn’t need “Balenciaga” splashed across the chest. We’re talking Old Money, Preppy, and Ivy League—three styles that reflect an origin. And an education.
Three ways of dressing—but more importantly, three ways of carrying yourself through life.
👑 Old Money
It’s the style of those born into wealth—not of someone who just cashed in on crypto or forex. It doesn’t flaunt price tags; it showcases heritage. So forget flashy logos and loud flexing. Think premium fabrics, flawless tailoring, and understated details.
“Old Money” is the aesthetic of those raised among polo matches and exclusive clubs, where elegance is passed down like a family heirloom—not clicked into a shopping cart on Zalando.
Double-breasted navy or charcoal wool blazers. Lightweight wool suits. Crisp poplin shirts in white or sky blue. Thin cashmere pullovers worn under a jacket or over an Oxford shirt, in neutral tones like beige, ivory, light grey, camel. And the shoes? Only genuine leather, hand-stitched. Derby shoes, monk straps, or—if you really want to flex that aristocratic bloodline—a perfectly worn-in pair of driving loafers. It’s not fashion. It’s legacy.
🏈 Preppy
Born on the elite campuses of American prep schools and perfect for guys aged 16 to 25, this is the style of rich kids with that smug look—the ones who steal your girl without even trying.
Piqué polos with the collar popped, in pastel shades or stripes, worn with cocky confidence. A Harrington jacket to go from comparative law class straight to brunch with the ambassador’s daughters. Slim-fit chinos in beige or off-white, rolled just above the ankle (yes, this is the only time rolled cuffs are allowed). A sweater casually tossed over the shoulders.
Accessories? Maybe a retro-inspired sports watch. Finish with a pair of tassel loafers—Tod’s or Sebago—and that golden boy smile that says loud and clear: “Yes, I’m still young… but I’ve already won.”
🎓 Ivy League
The older, brainier cousin of Preppy. It’s the style of the senator’s son who reads Hemingway and plays squash. The kind that conjures images of Harvard, Yale, and Princeton.
Oxford shirts, slim knit ties, deconstructed blazers, and leather loafers. Tweed jackets, regimental ties, silk pocket squares… and that vibe of a man who quotes Kant but fucks like a rabbit.
This is the Preppy who’s studied, traveled, and now rules the social scene. It’s the signature look of a refined man discussing geopolitics over bourbon in a leather-walled lounge.
⚠️ Never Adopt an Attitude of Superiority
Dress consciously. Always. Pay attention to the details, choose cuts that flatter your body—but never slip into arrogance. The sense of superiority is the enemy of true style. A refined man has no need to look down on others. A man who does, even if he’s wearing the finest suit from Savile Row, doesn’t come off as sophisticated but simply ridiculous.
Kindness and humility are essential parts of real elegance. We’re not talking about fake modesty or hypocritical niceness, but that natural distinction that doesn’t need to show off—because every gesture speaks of balance, respect, and class.
Remember: dressing like a gentlemen isn’t enough, you’ve got to be one. A lout in a perfect suit is still just a well-dressed lout.
💥 The Scent of a Man
Your fragrance speaks for you even when you keep your mouth shut. It’s like an invisible signature. But beware: it must be used wisely. A man who knows he’s desirable doesn’t need to smell like a prostitute in a late-1800s brothel. There’s a wide variety on the market. Here are a few key pointers:
🧴 Cologne
Timeless. Leather. Tobacco. Vetiver. Sandalwood. All great notes—if you know what you’re doing.
Just don’t slip into accidental vintage mode, or worse, the “1950s barber shop museum” effect. That “old-school masculinity” hits the right note—but only if you dose it right.
Pick one that doesn’t smell like your grandfather’s medicine cabinet. And as always, moderation is everything: one spray on the neck, maybe one on the wrist—and that’s it. Not on your sweater. Not on your scarf. And definitely not in your underwear.
⚪ White Musk
Warm, enveloping, sexy.
But go easy. You want to leave just a whisper in the air—not a chemical trail that triggers a fire alarm.
🍃 Basil
Unexpected. Sophisticated. Cultured.
It’s for men with refined taste. But remember: basil, not pesto.
🍋 Citrus
Bergamot, lemon, pink grapefruit.
Fresh, bright, ideal for daytime—especially when you want to be the guy who smells like he just got out of the shower. Avoid anything too sugary though, or you’ll smell like a walking mojito.
❌ Vanilla
Danger zone. Way too sweet.
You might walk into a bar and have the first woman at the counter say: “Who the hell lit a giant Yankee Candle in here?”
💀 Tattoos and Overgrooming
A true playboy doesn’t need to obsess over his looks. So ditch the eyebrows shaped like bird wings, the full-body waxing and the UV tanning lamps—seriously, stick to real sunlight: tanning beds age your skin, and fake tans just scream cheap. Let’s face it—that whole “mirror, mirror on the wall…” vibe reeks of insecurity. Definitely not alpha male material.
As for tattoos, the real-deal playboy turns his nose up at them—he sees them as childish. Sure, they’re all the rage these days, I get it. But a seducer doesn’t follow trends because his style is timeless.
So even if you’re into ink, go easy. With a body like Spizoiky’s, you’re more likely to end up on a reality show than in a woman’s fantasies. True elegance absolutely forbids tattoos—but hey, given the times we live in, we can afford a little flexibility… just don’t go overboard. Remember: you’re not a tribesman from the African jungle, nor a member of a South American drug cartel!
⚠️ Elegant, Not Foppish!
Careful now: a playboy is elegant, not foppish. The difference may be subtle, but it’s absolutely essential. Mess that up, and you’re done. To be foppish means dressing with excessive, ostentatious, affected care. The word “foppish” oozes mockery: it describes a kind of so-called elegance that’s stiff, contrived, overworked and hopelessly artificial—more a mannequin than a man, more a caricature than a seducer. It’s the appearance of someone desperate to be noticed—a fop, a prissy little poser, and more importantly, not a playboy.
Being foppish means looking fake, overly groomed—practically embalmed. The foppish man is dressed, polished, and styled with obsessive precision. His refinement becomes a pose, and his devotion to detail makes him look ridiculous.
A playboy isn’t one of those preening little fops parading around day and night with perfectly sculpted hair, frozen in place, beards trimmed to 0.2 cm, skinny trousers vacuum-sealed to their thighs, and tiny blazers buttoned all the way up like armor. He doesn’t move through life with the stiff posture of a mannequin headed for a tailoring catalog shoot –terrified of wrinkling his shirt or soiling his mirror-shined shoes.
The playboy’s elegance is relaxed, natural, and effortless. It’s the ease of someone completely at home in both his outfit and surroundings. He doesn’t dress to be seen but dresses to enjoy himself. There’s no stiffness. No fakery. Just genuine charm with a knowing, carefree touch.
So yes, take care of yourself. But don’t overdo it. Don’t fall prey to the demon of detail. Because nothing betrays insecurity—or reeks of inauthenticity—more than a look that’s too perfectly polished and calculated.
🚨 “Suit up mode: activated!”
As the great Barney Stinson teaches us: “Suit up mode: activated!” Because dressing well isn’t just about impressing others—it’s about reminding yourself who the hell you are.
A killer suit is a shot of pure self-esteem: it turns you into another man. It straightens your back, sharpens your gaze, changes your stride. Elegance, among other things, is high-octane fuel for self-confidence. And self-confidence… well, that’s sexy as hell.
Can’t wait to read it all? Get the book. Break the rules. Rule her world 👇
