While the person I care most about helping with this book is you, the fact remains that you are eventually going to be faced with having to assist at least one of the dudes in your life with getting his sartorial act together. When that time comes, you can just cut these pages out, pass them over, and consider your work done. But that doesn’t mean you shouldn’t peek over his shoulder while he reads—because having a working knowledge of men’s clothing and style challenges will come in mega-handy when your boyfriend/brother/clueless coworker suddenly needs to look sharp for a major life event (or if you want to dabble in rocking some menswear yourself)! I love dressing male actors simply because men’s clothes have so many rules. While the rules for women’s fashions are kind of dumb and were made for some serious breaking, classic menswear is all about angles and geometry—so it’s a foolproof, mathematical equation that adds up perfectly almost every single time. So much of fashion is pure, glorious, disorganized chaos—but there’s a sort of sweet relief in having one single area where order, logic, and strict adherence to style formulas rule the roost.
The cornerstone of proper men’s fashion is the humble suit, and wearing one is also the thing that throws most guys for a loop—especially if they are the type of dude who only wears them to weddings, funerals, and job interviews. Awards season in Hollywood is the thing that always stumps the men I dress—suits and tuxedos are the very last thing most guys would usually reach for in their closets. But before you get to playing celebrity stylist, let’s discuss how men’s clothing is actually meant to fit in the first place. Because as you know by now, proper fit is important. And if something doesn’t fit right, it’s never going to be stylish.
The humble jacket (also known as a blazer) is probably the most important part of a man’s look—and a good-looking jacket starts with the shoulders. Remember in chapter 2 when I said that any garment with a poorly fitted shoulder is best avoided? Well, I’m saying it again here. The shoulder is the foundation all else is built on, and if it’s wrong, nothing about a jacket is ever going to be right.
A well-fitted shoulder will lay perfectly flat. The seam on top of the shoulder should be the same length as the shoulder bone underneath it and should meet the sleeve of the suit right where the arm meets the shoulder. If the point where the sleeve connects to the jacket is hiked up on the shoulder bone, the jacket won’t sit properly. A jacket with a bad shoulder fit will cause an endless amount of lumps, bumps, and wrinkles on the sleeve and at the top of the jacket that no amount of tailoring or alterations can solve.
It’s also important to check how the front of a jacket closes over the body. For a single-breasted jacket, close either the top or middle button—even if it’s a three-button jacket. The jacket should then meet neatly without the lapels hanging too far forward, which would indicate that it is too loose. If buttoning the jacket causes it to flare out at the bottom, this means the jacket is likely too tight. The buttons should close easily, and there should be no wrinkles beneath the closure. The area below the button should never pull so far apart so as to expose a triangle of shirt above the trousers when standing still. (But when dancing, all bets are off!)
A good sleeve-length guideline for the relationship between a jacket and the shirt worn under it is to always have about a half inch of shirt cuff visible beyond the jacket cuff. Keep in mind, this is only a guideline—styles change with fashion all the time. The only hard-and-fast rule when it comes to sleeve length is that the jacket should never hide the entirety of the shirt cuff. At least a tiny band of sleeve should always be visible. This means that the jacket sleeve will usually end just above the wrist bone. But when in doubt, remember: Flashing a half inch of sleeve will never be considered “wrong.”
The ideal length jacket should fall past the waist and drape over the top of the curve formed by the backside, with the hem of the jacket hitting at right about the middle of a cupped hand. If a jacket is sitting on the very top of the butt, creating a small flare in back, it’s too short. If a jacket covers the backside entirely, it’s too long.
It’s quite easy to tell a properly fitting jacket collar from a bad one. For starters, a jacket collar should rest against the shirt collar with no gaps in between. Any space between the shirt and jacket means the collar is too big. A too-tight jacket collar will be a littler harder to diagnose—it will only show itself at the back of the jacket. You’ll notice bunching and folds just beneath the collar if it’s too tight, and it will often cause wrinkles on the shirt collar as well. A bad collar fit could be the result of a neck size that’s wrong for you, but more often than not, it’s a sign of a much larger fit issue—such as the dreaded bad shoulder.
The backside (also known as the seat) of a pair of trousers should hang in a smooth drape over the rear end, without pulling tight across it or draping too loosely down the thighs. A bad seat will cause either horizontal wrinkles just under the bum (too tight) or sagging at the backs of the thighs (too loose). A tailor can take in the seat somewhat, but there’s a limit to how much he or she can do. If the seat is ultraloose, the fit can’t be adjusted too far without pulling the pockets out of place. And unless there’s a rather large amount of extra cloth in the seat seam of your pants, they can’t be let out very far to make a tight pair looser. So when buying a pair of pants, remember: Better to have them a bit too loose than at all too tight.
The break of a pair of pants is the small wrinkle that appears where the top of a shoe cuts into the trouser hem. It should be a small, subtle feature—one single, horizontal dimple is perfect. The pant leg should rest on the top of the shoe, but shouldn’t slouch down much farther. Most better dress pants (and almost all suit pants) are sold unhemmed so they can be hemmed to the best length for the wearer.
A good fit rule for the collar of a shirt is to ensure that only one finger fits comfortably between the collar and neck. If two can fit, it’s a sure sign that the collar is too big.
The shirt body poses a special fit issue. Oftentimes, a shirt that fits across the shoulders will be so billowy at the back and torso that you’d think the wearer was hiding a backpack under there. Finding a slimmer cut shirt that also fits through the shoulder area is no small feat—but a shirt that is far too blousy through the body does the wearer zero favors. Persevere until you find the fit that works best for you. Also, the shoulder seams of a well-fitted shirt should hug the shoulders—and shirt cuffs should reach just past the wrists.
Now you know how basic men’s garments are supposed to fit—but you might not have a clue how to determine your correct size. Don’t fret, because knowing one’s measurements isn’t a luxury reserved only for fancy people. Anyone with a tape measure, pen, and a little bit of patience can measure themselves the exact same way a costume designer would—and look far better in their clothes as a result.
The measuring guidelines below are most useful when looking to buy a suit or dress shirt and slacks, but having your measurements at the ready is invaluable, no matter what the goal of your shopping trip.
Suit and sport coat sizes consist of one number and one letter: 38S, 40R, or 42L, etc. The number corresponds to the chest measurement, while the descriptive letter (which, means short, medium, or long) refers to the length of the jacket—which is based on height. Start out by wrapping a cloth tape measure under your armpits around the fullest part of your chest, making sure the tape is fully crossed over the shoulder blades in back. The tape measure should be snug—not so snug as to constrict your breathing, but not so loose that it slides down. And don’t hold your breath, as your chest will then be unnaturally puffed out. The resulting number is the first part of your suit size—and will likely be anywhere from about 36 to 56. If you are between five feet four inches and five feet six inches, you are a Short. A height of five feet seven inches to five feet eleven inches means you’re a Regular. And anyone six feet or over is most definitely a Long.
The waist measurement of the pants that come standard with an off-the-rack suit will correspond to your jacket size by going down six inches. This means that if your jacket is a size 40, the pants that accompany it will have a thirty-four-inch waist. Obviously this formula doesn’t work for all body types, and men who have a greater or lesser measurement difference will be far better off looking for suit manufacturers who offer separates.
To buy a dress shirt, you’ll need to know both your neck and sleeve measurements. To determine your neck size, grab the tape measure and wrap it around the lowest part of your neck, about an inch below your Adam’s apple. Take care not to choke yourself with the tape measure—for a comfortable fit, you’ll want to be able to fit one finger between the measuring tape and your your neck. When in doubt, round up to the next half inch.
Taking a sleeve measurement properly is a two-person job. You’ll want to stand with your arm slightly bent at the elbow and your hand on your hip. Your helper should run the tape measure from the very center back of your neck, across your shoulder and elbow and down to just past your wrist joint. The resulting number will be anywhere between twenty-nine and thirty-nine inches, and once you know this number, you’ll be amazed at how much better you suddenly look in a dress shirt.
Measuring the waist can be a bit tricky, as many men prefer to wear casual pants down around their hips instead of at their natural waists. While this works for jeans and other casual pants, it doesn’t fly when you’re being fitted for a pair of dress slacks or trousers. You’ll want your real, actual waist measurement—taken at around navel level, making sure to put a finger between your body and the tape measure to ensure your pants don’t dig into your flesh uncomfortably. The resulting number is your waist size.
Knowing your inseam measurement will save you the cost and hassle of having every pair of pants you ever own hemmed. To figure out what it is, start by standing with your shoes off and hold the end of a tape measure comfortably at crotch level. You don’t want to hold it too low, but you also don’t want to cram it too far up either. The resulting number is your inseam measurement, and when coupled with your waist measurement, allows you to try on far fewer pairs of pants to find the one that actually fits properly.
Now that you know how a suit is meant to fit and how to measure yourself for one properly, how about delving into a little bit of the history of this amazing garment? Because the modern suit really is a miraculous invention. A great suit has the ability to transform even the most slobbish wearer into a creature who at least appears to have his life together. The model for modern male elegance in a suit will forever be Edward, Duke of Windsor—also known as Edward VIII, the man who abdicated the throne of England after meeting and falling in love with divorced American Wallis Simpson. The Duke is responsible for establishing innovations in men’s suiting fashions during the 1920s and 1930s that remain popular to this day. If you’ve ever tied a Windsor knot or seen a Windsor collared shirt for sale in a store, you’ve felt his sartorial influence. Before the Duke, menswear was still stuck in the rigid style parameters of the late 1800s. He cut a debonair figure through the early twentieth century with his easy-cut suits, fresh pattern combinations, and body conscious silhouettes, all of which are now hallmarks of the modern suit.
Looking good in a suit is actually far easier than most guys realize, because a well-cut suit can create an athletic shape where there previously was none, elongate a truncated torso, or camouflage a large belly handily. There’s really a suit formula for every single body one could possibly have.
Once you determine what style of suit to buy, the question of when and how to button it up still remains. The short answer is that suit jackets are meant to be buttoned when standing (to provide a “finished” look) and unbuttoned when sitting so as to keep the fabric from bunching up unflatteringly. Now we’ve answered the question of when to button, but you’re likely wondering which exact buttons you’re meant to do up when—and how. Luckily, the art of buttoning isn’t all that hard to pick up if you remember three little words: sometimes, always, never. This handy phrase works all the time—whether a suit has one button or three. The top button is your “sometimes” button, with the middle and bottom buttons following as “always” and “never,” respectively. This is also a good time to tell you that a suit with more than three buttons isn’t a suit—it’s an abomination. Never allow any dude in your life to buy or wear one.
On a three-button suit, our “sometimes, always, never” mantra stays intact. On a two-button suit, the top (or “sometimes”) button goes away. And on a single button suit, everything except “always” falls away. But one thing never changes: on a suit with two or more buttons, the bottom button is never, ever buttoned up. Legend has it that the custom of leaving one’s bottom suit jacket button open grew out of King Edward VIII’s ever expanding belly in the late 1800s and early 1900s. The more he ate, the harder it was for him to button up his coat, so he finally did away with buttoning it entirely—and thus, a fashion trend was born. But that was well over one hundred years ago, so you may be wondering why this buttoning rule lasted so long. The reason is simple: it actually does make a suit jacket look better! When you button the last button on a suit jacket, it tends to restrict movement and pull over the hips. It also causes the fabric to bunch up unattractively when you put your hands in your pockets. Leaving the bottom button undone allows the jacket to lay nicely as the body inside the suit goes about its daily business.
I once had a young actor who told me I was dead wrong, and that buttoning one’s bottom button was perfectly acceptable. I, of course, politely told him he was incorrect, but he insisted. Rather than argue with him about it at length, I decided to call a comedian pal, who just so happens to be the most dapper man alive and an expert on all things having to do with men’s style. I put him on speakerphone with the actor in the room and asked, “Can this young man button the bottom button on his suit jacket in this scene?” To which the comedian casually replied: “It depends. Is he currently standing in a blizzard?” That was the end of that conversation, and yet another dude in Hollywood now knows the golden rule of suit buttoning by heart.
Your knowledge of suit etiquette can be determined by how you answer to one single question: When is it acceptable for a man to remove his suit jacket in public?
A: Never.
B: When alone in his personal office, on a plane, or in a car.
C: Whenever he is hot.
D: At a wedding reception.
This is a bit of a trick question as the answer is basically A, but also a touch of B. The old-fashioned rule is that a man should never remove his suit jacket when a woman is present, but that should be expanded to say “when other human beings are present.” This rule still applies in all business settings and for occasions of any formality. (Yes, this includes wedding receptions and business lunches.) You can obviously remove your jacket when traveling in a plane or car—and in your own office when you are the only one present, it is perfectly acceptable to remove your jacket while you work and hang it on the back of the chair. But the moment someone enters your office, best practices demand you pop your jacket back on if you want to be taken seriously.
Having said all this, I do believe there is a point in every wedding celebration where debauchery takes hold and removing one’s jacket becomes perfectly acceptable. (Hint: It’s usually a few hours and a few champagne bottles past 1:00 a.m.) A good rule of thumb is that if the bride’s parents have left the building and more than five women have removed their shoes, you’re probably in the clear to lose the jacket and dance with sweaty abandon. Until then, keep your suit jacket on tight. If you find that you are uncomfortably hot, it means your suit is made of the wrong material for the weather. Look for seersucker or tropical-weight wools for summertime suit-wearing scenarios.
Let’s say you already own a suit but don’t often get a chance to wear it—and as a result, it either doesn’t fit anymore or you think it might be a little outdated. You’re probably wondering if having it altered is worth it, or if all hope is lost. The correct answer depends on many factors, but the main one is the condition of the suit. If the fabric has become shiny in any area or the cuffs, belt loops, or lining are worn, don’t bother. You’ll be throwing money away by attempting to tailor it.
As far as fit goes, the most a suit can be altered is to accommodate about twenty pounds in either direction. After that, there are limitations to what can be done to let out or take in a suit before it starts to get proportionally awkward. Two inches from a waistband and about the same around the trunk of a jacket is about the max you can expect to fiddle with a suit before it goes out of alignment and looks bad. And if the shoulders of the suit no longer fit properly, it’s time to say goodbye. Lastly (but most importantly) attempting to make a double-breasted suit into a single-breasted suit is wasted money, and you can’t make a pair of pleated pants into flat fronts. I’ve had some success having my tailor stitch down the very top of the pleats on a pair of pants to cut down on the “balloon” factor, but it sometimes looks awkward and is best saved for a suit that otherwise has nothing wrong with it. It also works better on cotton suits (like seersucker), since the entire vibe of such a suit is inherently more casual than a wool one.
While it’s true that the higher the quality of a dress shirt, the less likely it is to be see-through, sometimes even the most costly shirts can leave a little too much showing for polite company. Luckily, this problem is easily solved by wearing a simple, short-sleeved, crew-necked cotton undershirt. An undershirt also helps keep the front of your dress shirt smooth and tucked in, as the friction between the shirt and undershirt keeps things nice and even. But you may be wondering: “What about when I take my jacket off and you can see my short undershirt sleeves through my dress shirt?” Well, you’re not taking your jacket off unless you are traveling or alone, remember? So it doesn’t really matter that you can see your undershirt sleeves—because you are the only one who is ever going to see them.
While there are endless ways one could tie a tie, I believe there’s only one knot you really need to know: the four-in-hand. This is the classic knot favored by businessmen, schoolboys, and lawyers the world over. The size of the four-in-hand knot is on the smaller side, making it ideal for button down and narrow-set collars, although its exact size is dependent on the thickness of the tie’s material. The four-in-hand is the epitome of simplicity and style, and if you learn how to tie only one knot, this is it. (It’s actually the only one I know how to tie without fear, and I taught myself how to tie it on an actor while in a moving car using instructions I pulled up on my phone!) It will never fail you as it works well with most ties and almost all types of shirt collar. It’s also the knot James Bond uses—need I say more?
If you are faced with a shirt that has a wide “spread” (which is the space in between the collar blades), you’re going to need to know how to tie a fuller knot to fill in that space—such as the Duke of Windsor’s namesake Windsor knot. (I can’t ever tie one properly without having to consult the Internet each time, so don’t feel bad about not knowing how to tie one already.) The Windsor is the bulkiest knot there is, and the best thing about it is that it stays in place without slipping. A larger knot also has a tendency to draw attention away from the face, so the Windsor looks best on those with a strong jaw or copious amounts of facial hair, as it then helps to strike the proper proportional balance.
Every man will have to wear a tuxedo at least once in his life, even if it’s just to the high school prom. Wearing one isn’t as daunting as it seems, because a tuxedo is essentially just a really fancy suit. While patterned cummerbunds to match your date’s dress are de rigueur for teenagers, wearing a tuxedo as an adult calls for a different set of rules. Even a rental tux can have a bit of savoir faire, if you just know what to ask for. I am of the opinion that if you are going to wear a tuxedo, you’re going to want to go all the way. For this reason, opt for a peaked lapel or slim-cut shawl collar. A notch lapel (as found on most business suits) is far too casual.
The number of buttons your tux has depends on your build—just like a regular suit. A two-button tux is a perennial classic, but the fit of a three button style on a taller, broader-shouldered man cannot be underestimated—it creates a flattering “V” shape where a two-button suit tends to gap and pull through the armpits. What’s “hip” and what happens to “fit” are two entirely different things, and both should be taken into account when looking for the right tuxedo.
Even if you’re stuck with a rental tux, there are still small things you can do to make it look a little richer, a little custom, and a little more special. I like to look for tuxedos that have ribbed silk faille trim on the lapels and pant legs instead of smooth, shiny satin. It’s what couture tuxedo-makers like Prada use, and it’s an easy way to get a richer, classic look on a cheaper tux.
While the jacket and pants are technically the most important parts of a tuxedo, the shirt you wear matters, too. You want a 100 percent cotton tux shirt, not a thin polyester one. Buying your own slightly higher-quality tuxedo shirt instead of making do with a rental will cost you about fifty bucks and is a great cheat to hide a lesser-quality tux. I like a classic fold-down collar shirt in place of the somewhat dated 1980s-style wing collar, and the good thing about it is that you can then choose to wear either a simple straight or bow tie. But beware: While a fold-down collared shirt looks good with any tux, a bow tie looks best with a peak lapel tuxedo, and a straight tie suits a long, lean shawl collar tux perfectly.
If you choose to wear a bow tie, another good cheat to make your whole getup look more expensive is to spring for a real, old-fashioned, hand-tied bow tie. Make sure you buy one that matches the trim on your tuxedo’s lapel and pants leg, and have someone at the store tie it for you, making sure to keep two fingers under the band to ensure it’s tied somewhat loosely on the neck. You can then carefully snip the tie at the back of the neck and take it to a tailor, asking them to stitch down the bow in front and add a strip of Velcro or a hook at the back so you can easily put it on just like an adjustable one. While this might seem like a ridiculous amount of work, nothing kills a formal look faster than an adjustable metal clip showing anywhere on your tie band. The Velcro cheat is one we use on any show that calls for a bow tie, as hand-tying one is a skill that not even many costumers have.
But what about cumberbunds? While patterned or brightly colored ones are indeed a hallmark of the prom-style tuxedo look and have no place on a grown adult, that doesn’t mean you can do away with one entirely. The rules of tuxedo wearing dictate that you must have something to hide the awkward transition between the shirt’s edge and the workings of the trousers’ waistband. Letting this seam fly free and uncovered is akin to a woman walking out of the bathroom with her skirt tucked into her underwear and her panties flapping in the breeze. A tux worn without the waistband covered is an incomplete look and a grave fashion faux pas. If you opt for the classic cummerbund look, wear it pleats up and make sure it matches the fabrication of your tie, which then in turn matches the lapels of your jacket and the trim of your pants. If a cummerbund isn’t your speed, you can opt to wear a vest (either full-backed or cutaway) to cover your waistband instead. But if you think wearing a vest then gives you license to remove your jacket in public, you are dead wrong.
I know exactly what you’re thinking after reading all this nonsense about waist covering: “But I see movie stars on the red carpet not wearing a cummerbund all the time!” There is some truth to this statement, but let’s separate a little fact from fiction here. Almost without fail, the stars working this uncovered waistband look have tux pants that are specially designed with a slightly wider satin-covered waistband as a stand-in for a cummerbund. Secondly, their outfits have been chosen with only one purpose in mind—standing on the red carpet and having their photo taken. And even with their jackets closed, these stars still sometimes have a bit of unflattering white shirt peeking out when they put their hands in their pockets, causing the jacket to spread apart. Pulling this same look off in real life is quite the challenge. Rules in formal wear exist for a reason, and if you want to be taken seriously, it’s worth taking the time to learn them. (Or at least be aware of them so you know when you are breaking them.)
As if we didn’t talk about buttons enough earlier in this chapter, let’s have a few more words about them now. Some fashion purists still insist that leaving your shirt buttons exposed on a tuxedo shirt is up there with showing your waistband on the list of tux-wearing “no-nos.” The truth of the matter is that exposed shirt buttons are actually perfectly acceptable in this day and age. But, if you want to go old-school, you have two choices to solve this problem: either choose a shirt with a covered button placket or get yourself a set of button covers.
If you choose to go the button cover route, I like the look of simple white satin ones so they blend in with the shirt. When a stark white shirt (unfettered by distracting plastic buttons) is set off by a beautiful hand-tied bow tie and a proper waist covering, everything but a man’s face and personality falls away, allowing both to shine. And that’s the real reason for rules in suiting and formal wear—to let the man in the suit be front and center, without a lot of faddish, complicated clothing choices mucking up the works.
Unless you are attending an incredibly formal event at the request of a European monarch, you can do away with the dated, old-style patent leather tux shoe. I much prefer a cap- or rounded-toe dress shoe done up in super-shiny smooth leather. As for the somewhat recent trend of wearing sneakers with a tuxedo to a wedding, they are no more appropriate there than they would be at a court appearance. The point of a tuxedo is to dress up for once in your miserable life, so go ahead and wear a pair of big-boy shoes for a few hours, would ya?