Chapter 2
The
GENTLEMAN
Courtesy is as much a mark of a gentleman as courage.
—Theodore Roosevelt
THE ANCIENT Greeks called their gentlemen kalos kagathos, and required that they be well-groomed and well-dressed, take part in cultured discussion, and exhibit an even temper, physical strength, and bravery. In 9th-century BC China, the I Ching served as a guide for would-be junzi, or men who pursued the virtue of ren. Confucius described such a man as one who “wishing to be established himself, seeks also to establish others; wishing to be enlarged himself, he seeks also to enlarge others.”
Today, a gentleman cares about how he looks and how he behaves. Put simply, he gives a damn. He strives for polish not out of vanity, but out of a concern for other people. His presence adds to the ambiance and texture of an occasion. When he practices courtesy, he uplifts those with whom he interacts.
Gentlemanliness also requires strength underneath the polish. A gentleman’s respect is premised on restraint. That he could act as a barbarian, but instead chooses to behave with class, is what gives etiquette its power. As John Wayne declares in McLintock!, “You’ve got to be a man first, before you can be a gentleman.”
TIE A FULL WINDSOR NECKTIE KNOT
You’re about to go into a big business meeting. Your suit is perfectly fitted, your shoes are shined, your shirt is pressed. Which necktie knot do you go with? It has to make an impression, but not be flashy. It needs to convey power, confidence, and authority. The choice is simple—the full Windsor (also called the Windsor or double Windsor). This knot is often worn for more formal occasions and meetings: weddings, important business meetings, and presidential debates. Because it’s a large knot, it should be worn with a spread collar. For men who are stout, or have wider faces and necks, the Windsor will look proportional to your build and mug, and should be your go-to tie knot.
1: DRAPE the tie around your neck. Cross the wide part of the tie over the narrow end, and start to bring it up through the hole between collar and tie.
2: AFTER bringing it up through the hole, pull the wide end down toward the front.
3: BRING the wide end behind the narrow end and to the right. Then pull the wide end back through the loop again.
4: WRAP the wide end around the triangle by pulling it from right to left.
5: BRING the wide end up through the loop a third time, and pull it through the knot in front.
6: TIGHTEN the knot and center it with both hands.
TIE A BOW TIE
START WITH the tie around your neck, allowing the left end (A) to be a little longer than the right end (B). Cross end A over end B.
1: TAKE end A and tuck it up in the hole between your neck and tie.
2: FOLD end B at its widest part, holding it sideways. It should look bow-shaped.
3: DROP end A over folded end B. Fold end A up (insert).
4: THE tricky part: pass folded end A under and behind folded end B on your left and through the loop behind folded end B (insert).
5: TIGHTEN knot by holding both folded ends and pulling carefully. Straighten as needed.
CARRY A HANDKERCHIEF
Handkerchiefs are, well, pretty handy. While women carry a purse stocked with things like tissue packs, most men do not. And yet our noses run just as often. When you carry a hankie, you don’t have to scrounge for a tissue to deal with your dripping schnozz, or wipe your nose on your sleeve. And you can mop your brow with it when you’re sitting on the front porch drinking mint juleps.
But the best reason to carry a handkerchief has nothing to do with you. It’s the chance to lend it to others. Put one in your pocket when you go see a tear-jerker movie with your girlfriend or accompany your wife to a funeral. The offer of a soft hankie is a gallant and chivalrous gesture.
TIE A SCARF
Scarves are a great way to stay toasty when the winter wind comes biting. Sport any of these styles and you’ll be a dapper fellow about town.
The first three ways are for medium-length scarves, and will serve you well in cool temperatures—above freezing and into the 50s. The final two ways are for longer scarves, and are better for those days that dip below the freezing mark.
The Drape
SIMPLY DRAPE the scarf around your neck, with equal lengths on both sides.
The Once Around
DRAPE THE scarf around your neck, leaving the right side short. Bring the left side over your shoulder and around your neck to the front.
The Parisian Knot
FOLD THE scarf in half and drape it around your neck. Bring the loose ends through the loop and tighten.
The Overhand
DRAPE THE scarf around your neck, leaving the right side short, and crossing the left side over it. Bring the left side up through the loop in the neck and back out the front.
Reverse Drape
WITH THE scarf around your neck (equal lengths on both sides), take the right side and throw it over your left shoulder, and throw the left side over your right shoulder.
HOW A SUIT SHOULD FIT
While the number of jobs that require dressing up in a suit is declining, it’s still common practice for many businesses—and a surefire way to look sharp. Whether you wear a suit five days a week or only dust it off for a special occasion, it should fit well. Not only do ill-fitting suits look bad, they’re uncomfortable. From pinched arms to dragging pants, don’t settle for suits that are too big or too small—get them tailored just right.
Shoulder
THE SHOULDER line should be smooth. Too tight and you’ll see creases. Too loose and you’ll have rumpled sections.
Seat
PANTS SHOULD drape over the seat. Look out for bunching or excessive fabric that causes a billowy look.
Trouser Break
PANTS SHOULD touch your shoe and crease slightly in the front only.
Sleeve Length
SLEEVES SHOULD allow half an inch of your shirt to show.
Jacket Length
YOUR JACKET should meet the middle of your palm when your arms are relaxed at your side.
Jacket Collar
FIT THE collar to create a seamless transition between your neck and back. Avoid loose collars that pull away and tight collars that cause bunching.
Sleeve Pitch
WITH ARMS relaxed, the sleeve fabric should be smooth, not twisted or bunched.
Not only do ill-fitting suits look bad, they’re uncomfortable.
MATCH A SHIRT AND TIE
Nothing throws off a put-together ensemble like a mismatched tie. Keep these guidelines in mind.
1: BEGINNER—Match solid shirts with solid ties. Use contrasting shades of the same color, like a light-blue shirt with a dark-blue tie, or two contrasting colors, like a light-pink shirt with a navy-blue tie. When in doubt, set a solid color tie against a classic white shirt.
2: INTERMEDIATE—Match a patterned tie with a solid shirt or vice versa. The trick is to make sure there is a unifying or matching color between the shirt and tie.
3: ADVANCED—Match a patterned tie with a patterned shirt using these rules. One, the pattern styles must be different—like a striped tie with a checkered shirt. Two, the pattern sizes must be different. Don’t match a tie with tiny polka dots with a shirt that has a tight plaid pattern. Three, ensure there is a unifying or matching color between the tie and shirt.
COORDINATE YOUR SHOES WITH YOUR SUIT
Once you have your shirt and tie put together, you need to match your shoes to your suit. It’s not that complicated—but remember, your belt should always be the same color as your shoes.
1: NAVY suit—burgundy, brown, or black shoes
2: LIGHT-GRAY suit—burgundy, brown, or black shoes
3: DARK-GRAY suit—burgundy or black shoes
4: BROWN suit—burgundy or brown shoes
5: BLACK suit—black shoes
IRON A DRESS SHIRT
Growing up, dear old mom might have ironed your dress shirts whenever you needed it. But you shouldn’t need to rely on someone else to help make a strong first impression. Wrinkles make you look sloppy and out of sorts. Well-pressed clothing announces that you have your stuff together—that you’re a man of discipline who knows details matter. Ironing is easy: You can press a shirt in less than five minutes.
1: SLIGHTLY damp shirts are easier to iron than dry shirts. Remove the shirt from the dryer before it’s fully dry or moisten it with a spritz of water. Look at the shirt’s tag, and adjust the iron to the proper heat setting.
2: POP the collar and remove any collar tabs. Iron the underside of the collar first, slowly pressing the iron from one point to the other. Flip the shirt over and repeat on the other side.
3: IRON the cuffs. Unbutton one and lay it flat. Iron the inside first, then the outside, moving wrinkles from uneven fabric to the edges. Iron around the buttons, not over them.
4: IRON the shirtfront. Start on the side with buttons and work the iron point around each one. Then move to the top of the shoulder and work your way down. Repeat on the other side.
5: IRON the back. Start at the top with the yoke (back shoulder area) and slowly slide the iron down. If you have a center box pleat, spend a few seconds ironing around it.
6: TIME for the sleeves. Take one sleeve by the seam and lay it flat on ironing board. If you can see the crease on the top of the sleeve from previous ironing, match it.
7: START ironing at the shoulder and work your way to the cuff. Turn the sleeve over and iron the opposite side, then repeat with the other sleeve.
ROLL YOUR SHIRT SLEEVES
Some sleeve-rolling techniques are more appropriate than others, depending on the garment and occasion.
WHEN SHOULD YOU ROLL YOUR SHIRT SLEEVES? 
• When it’s a practical necessity. Anytime they might get in the way, get dirty, or get caught in a moving part—roll ’em up.
• When it’s hot outside. While the appropriateness of rolled sleeves varies by workplace, they’re acceptable most times you have direct sunlight on your skin.
• When the situation calls for casual. Rolled sleeves dress down attire that would otherwise be too formal or dressy for the occasion; they send a signal that says “relaxed.”
Suit or sport jackets usually aren’t rolled (and when they are, they are more pushed up than rolled) unless there’s an immediate and practical need. You can do it (if your jacket has working sleeve buttons), but be aware that it’s a fashion-forward look.
• BEST for: performing physical labor
• BENEFITS: simple and intuitive
1: UNBUTTON cuff and any gauntlet buttons farther up sleeve.
2: FLIP cuff back and inside out.
3: FOLD back, using the cuff to set the width, until band of rolled cloth is just below elbow—higher when engaging in physical labor.
• BEST for: casual dress, thin arms, layers
• BENEFITS: involves the least folding, easiest to unroll without wrinkles
1: UNBUTTON cuff. Undo gauntlet buttons according to preference. Flip cuff back and inside out.
2: FOLD over once, hiding cuff behind a band of sleeve fabric.
3: STOP there and tuck corners of cuff in neatly.
• BEST for: rolling sleeves with style, showing off cuffs with inner contrasting color
• BENEFITS: easy to adjust and unfold
1: UNBUTTON cuff. Undo gauntlet buttons according to preference. Flip cuff back and inside out.
2: PULL flipped cuff all the way to just below elbow without folding, turning sleeve inside out as it goes.
3: TAKE bottom of inside-out portion and fold it up until it traps bottom of cuff. Show as much of the inside-out cuff as you desire.
THE ART OF SHINING SHOES
Whether it’s an upcoming wedding or graduation, or simply another day at the office, a pair of shiny shoes sets you apart as a man who cares about the details.
Not only does shining your shoes add panache to your appearance, it is a necessary part of properly caring for and maintaining a nice pair of leather shoes or boots. The polish helps moisturize and waterproof the leather, lengthening the lifespan of your shoes.
1: REMOVE any dirt/mud/salt with brush or damp rag. Wait until dry.
2: RUB a moist cloth in the polish to acquire a small amount on the cloth.
3: APPLY the polish in small circles, in small amounts.
4: GRAB your shoe brush and brush the entire shoe vigorously.
Shining your shoes not only makes your shoes look good, but maintains them.
5: BREATHE “hot air” onto the shoe as if trying to fog a mirror on parts you want a really nice shine.
SHOE CARE 101
While regular shoe shining goes a long way in keeping your dress shoes in tip-top shape, it’s not enough. To ensure that you get miles and miles out of your shoes, incorporate the following shoe care tactics into your routine.
1: SHINE your shoes (here) after you buy them and before you wear them. Shine them regularly for as long as you own them.
2: WHEN you remove your shoes, insert a cedar shoe tree to draw out inner moisture and reshape the leather.
3: REMOVE a salt stain as quickly as possible by lightly applying a mixture of 2/3 water, 1/3 vinegar with a rag, wiping off with clean damp rag, and drying with a towel.
4: WATERPROOF your shoes with mink oil (may darken the color of the leather), a wax-based polish (light protection), or a specialty waterproofing compound (heavier protection).
5: CLEAN your shoes regularly to remove dirt, stains, and layers of built-up polish. Use a specialty leather cleaner, saddle soap, Murphy Oil Soap, or Ivory soap. Avoid products that contain detergents or acids.
6: TO keep your shoes from drying out, every few months apply a specialty moisturizing conditioner or buff in a dab of petroleum jelly.
7: IF your shoes are wet, stuff them with newspaper or a small towel to draw out the moisture. Replace the paper/towels periodically as they get saturated. Never place your shoes near a heat source; this can dry out and crack the leather.
8: REMOVE scuff marks by rubbing the scuff with non-gel toothpaste. Rinse, wipe, and let dry.
Note: The toothpaste trick does not work on every kind of shoe. Test the toothpaste on a small spot on the shoe to ensure compatibility with your particular leather.
9: WHEN your shoes become really worn out, send them back to the manufacturer for refurbishing or resoling instead of buying a new pair.
ANATOMY OF A DOPP KIT
A traveling man needs only a few essentials to be happy. Nevertheless, you do need a place to stow these items. Enter the Dopp kit.
You can get a nylon travel bag for under $5 at any big box store; they’ll get the job done. But if you want a Dopp kit with class, leather is the way to go. It will cost more, but last forever, age nicely, and become something you enjoy owning. It’s something you might pass down to your son or grandson, along with the stories of the places you took it.
THE GENTLEMAN’S ARSENAL
WHAT TO CARRY ON A DATE 
Help ensure a date goes well by being well-prepared with both the intangible, like confidence and charisma, and the tangible, like an umbrella.
1: HANKIE—It’s old school, but a clean linen handkerchief can mop up tears during a sad movie and wipe away spills at dinner.
2: CASH—Don’t risk the chance that you’ll encounter a business that only takes cash, leaving your date to pay for… your date.
3: MINTS—Take care of that garlic breath after dinner so you’re ready for an up-close chitchat or a kiss.
4: UMBRELLA—Check the weather before you go, and carry an umbrella in case the clouds open up.
5: SPORT coat—Dressed up or dressed down, a sport coat is the ultimate go-to clothing item for any date—and the perfect thing to offer your companion on a chilly walk.
SHAVE WITH A SAFETY RAZOR
Learning to shave is a rite of passage that has faded alongside the rise of expensive disposable cartridge razors and electric razors that require little skill to operate and deliver lackluster results. To get a close, smooth shave your grandpa would be proud of, go back to a double-edged safety razor—or skip right ahead to shaving with a straight razor (here).
1: SOFTEN your facial hair by taking a shower or wetting your face with a hot towel.
2: PUT a dollop of shaving cream into a small cup and work it into a lather using your brush.
3: APPLY shaving cream to your face with the brush, completely covering your facial hair using swirling motions to create a smooth, even surface.
4: DRAG the safety razor with the grain of your hair, not against it, at a 45-degree angle, using only the pressure of the razor against your face.
If you must apply pressure to cut through your stubble, replace the blade—it’s dull.
5: GO for beard reduction rather than removal. You may not get everything on the first pass. Use multiple passes if needed to get the skin completely clear of hair.
6: RINSE your face with cold water to close the pores. Apply your favorite aftershave to soothe your skin and reduce irritation.
SHAVE WITH A STRAIGHT RAZOR
Few things are manlier than taking a straight razor to the side of your face and deftly skimming off stubble. The straight razor is the samurai sword of shaving, but beyond its aesthetic and cool-factor benefits, it’s the best way to get the closest shave with the least irritation. It’s why high-end barbers still offer straight razor shaves to distinguished men needing a special shave before an important event or night out. Properly used, a straight razor will give you the best shave of your life.
1: SOFTEN your facial hair by taking a shower or wetting your face with a hot towel.
2: PLACE a small amount of shaving cream into a small cup and work it into a lather using your brush.
3: APPLY shaving cream to your face with the brush, completely covering your facial hair using swirling motions to create a smooth, even surface.
4: HOLD the safety razor so that your thumb is alongside the blade, your pinky supporting the handle, and your three middle fingers supporting the back of the blade.
5: DRAW the blade with the grain of your facial hair at a 30-degree angle, using light pressure and even strokes.
6: REPEAT the process with more shaving cream, going across the grain of your hair on the second pass, and again with the grain of your hair on the third pass.
7: RINSE your face with cold water to close the pores. Apply your favorite aftershave to soothe your skin and reduce irritation.
Keep your razor sharpafter each use by drying it and drawingit against a taut leather strop.
USE ALTERNATING strokes to drag the blade along the leather away from the blade’s leading edge. Strop it before your next shave, as well.
TRIM AND STYLE YOUR MUSTACHE
If you decide to grow a cookie duster, you’ve got the responsibility of keeping it in tip-top shape so that it’s presentable to the rest of the world.
1: TRIM your mustache weekly. First, comb dry mustache with a fine-toothed mustache comb. When wet, hair can appear longer, leading you to cut off too much.
2: USING mustache scissors or an electric trimmer, trim first for shape, cutting along bottom of ’stache and then outer edges. Work from middle toward one side, then to other side and back to middle. Look straight ahead and maintain a neutral face to get a smooth, even line.
3: NOW trim for length. Comb through the ’stache and cut hair on the outside of the comb to desired length. Trim conservatively at first. If using an electric trimmer, move from longer to shorter guides. You can always trim off more, but you can’t add it back after you’ve clipped it.
4: COMB through your mustache one last time, and clip any hairs you may have missed.