Rule 1: It’s more important to look good every day than to look different every day.
This is the genius of being a man.
Rule 2: Wear a tie when you’re asking for money.
In the days of Mad Men’s Don Draper, business attire was simple: Suit, tie, hat, and polished shoes. No wonder that generation was able to invent such marvels as space travel and the automatic coffee-maker: People weren’t distracted figuring out what to wear each morning. Nowadays the office looks more like the cantina in Star Wars, with slackers and dandies breathing the same filtered cubicle air. Hence the ongoing confusion: Should I wear a tie to this meeting? It’s simple: Wear a tie whenever you’re trying to make money gravitate from another person’s pocket into yours.
Rule 3: The rule of shoes: Black is basic. Basic is boring
If you’re wearing black, then by all means wear black shoes. But if you’re wearing gray, blue, tan, or a combination thereof, brown shoes will almost always look more sophisticated. There’s simply more range, from caramel to chestnut to chocolate. If you wear a belt, it should (sort of) match.
Rule 4: Thin with thin, thick with thick
Narrow lapel? Narrow tie. Thick lapel? Thick tie. This is why Howard Stern and Beth Ostrosky look good together. Arnold and Maria? It was never going to work …
(Emporio Armani suit, $1,400, select Emporio Armani botiques; Ike Behar shirt, $135, Bloomingdale’s; Thomas Pink tie, $105, thomaspink.com; tie bar, $100; hankerchief, $10; Emporio Armani shoes, $500, select Emporio Armani boutiques; Cole Haan Turino zip-top briefcase, $700, colehaan.com)
Rule 5: By the time you realize you need a haircut, everyone else has, too
Figure out how long you should go between haircuts. (Hint: This interval will shorten as you grow older. Just ask Gary Busey.) Schedule them in advance—every 6 weeks, or whatever works for your hair. If you wait until you need one, then you’re walking around looking like you need one. And masculine style is about looking like you don’t need anything.
Rule 6: A man wears a watch
Men used to wear pocket watches, round clunky things they stuck in their pockets and attached to their waistbands. A pocket watch was great for a guy, except when he was trying to discreetly measure the time between two job interviews or the time he had to finish up with the Dowager McMurtry and come a-calling on the Widow Jones. Then came the invention of the wrist-watch, and now a man could juggle employers and women with just a casual flip of the wrist, instead of having to yank a big clunky device out of his pocket. Sadly, this ingenious tactic is under siege: These days, many of us tell time not by wristwatch but by our cellphones. Great devices, unless you’re, well, trying to be discreet while digging one out of your pants. So we’re back to square one. Be a man. Wear a watch.
Rule 7: Vertical stripes make you look thinner
So guess how horizontal stripes make you look?
Rule 8: Good tailoring is job one
Rule 9: Don’t try to dazzle
Stick to basics for an interview to ensure that your qualifications are the focus. “Minimize patterns and loud colors,” Andre Johnson says. Choose a classic tailored suit in blue or gray, and add a pop of color with the tie or pocket square.
Rule 10: Be ready for anything—or anyone
Always have your A game on, Johnson says; in today’s market, you’re networking even in your off-hours. “When people first see you, they put you in a box, so you want to make sure you never look sloppy,” he says.
Rule 11: Have a go-to suit
“If you’re second-guessing yourself before an interview about whether something is too casual or flashy, don’t go for it,” Johnson says. Always make sure you’re comfortable, and know you can’t go wrong in your best suit and tie.
Rule 12: Be a road loafer
If you’re on the road for interviews or work, “pack nice loafers that you can wear with a suit and tie but also put on with jeans at night,” Johnson says. You’ll travel light. And slip-ons help you breeze through airport security.
Rule 13: When in doubt, go pink
Beige, yellow, and light-gray shirts should come with a warning label: “Not for use by men lighter than Dwayne Johnson.” That doesn’t mean yellow can’t look good on, say, Tim Pawlenty, but pale folks need to be careful because muted colors can make them look ashen or sickly. If you have a healthy tan, then by all means wear what you want. But if it’s mid-November and you haven’t seen the sun since Labor Day, be wary of wearing anything off-white next to your face. A great go-to color? Pink. Yeah, we know: In junior high, some jock made fun of you for wearing a pink shirt, and now you’re all scarred and emasculated over it. Grow up. Pink does exactly the opposite of beige: It makes a lighter-skinned guy take on a healthy glow, and it attracts women because it shows confidence.
Rule 14: Ties run button to button
A tie should cover your collar button and most of your top trouser button. Anything shorter makes you look like you work for NASA. Anything longer makes you look like former congressman Weiner.
(Calvin Klein Collection coat, $1,530, Calvin Klein Madison Avenue; DKNY suit, $600, 800-231-0884; Thomas Pink shirt, $185, thomaspink.com; Calvin Klein tie, $45, calvinklein.com; Frederique Constant watch, $2,750,frederique-constant.com; Boss Black shoes, $395, 800-484-6267)
Rule 15: Dress up to go shopping
This may sound kind of silly, but trust us—what you wear while you shop impacts what you’ll look like after you’ve shopped. It’s impossible to tell what a suit really looks like when you’re trying it on over your “I Hate LeBron” T-shirt. Similarly, it’s impossible to tell how well an overcoat fits unless you’re trying it on over a sport jacket. Wear a jacket, a white shirt, and a pair of formal shoes. Your tailor will thank you.
Rule 16: Square-toed shoes are just that
Perhaps you believe in always being prepared to kick a field goal no matter what the circumstances. In that case, opt for dress shoes with square toes. But assuming that you are not, in fact, Charlie Brown, the shoes that will last the longest and never go out of style should be a bit more rounded at the tip. Get the point?
Rule 17: Wear flip-flops only at home (okay—the beach, too)
What makes a man a man? He is strong. He is certain. He is prepared at any moment to meet a manly challenge with courage and fortitude. When a child wanders off the curb into traffic, when a date is hassled by a street tough, when a fire breaks out and someone needs rescuing, a man is there, fast and ready. He is not skipping cloppity-clop- clop down the street, squeezing his toes together so his flip-flops don’t fall off.
Rule 18: Ties are for dressing up
Rule 19: A good suit can be dressed down
A suit’s job is to make you look slimmer, fitter, stronger, and taller—that’s the magic of the matching jacket and pants. If you have that going for you, who cares if you throw a casual shirt under the suit and pair it with some cool sneakers? Just avoid logos, numbers, ribbed tees, or anything you’d wear to bed.
Rule 20: Don’t lace your wingtips like a sneaker
The crisscross lacing style you learned as a kid is fine for your canvas Chucks, not for a good pair of leather brogues. Try the more refined straight-bar lacing instead.
1 Thread the lace down through the pair of holes closest to the toe, making sure you have equal lengths of lace on each side.
2 Thread one end out through the next hole on the same side. Then string it across so it looks like a horizontal bar, and thread it in through the top of the opposite-side hole.
3 Lace it upward again, skipping one hole, and then pull the lace straight across. Continue this process, skipping one hole, all the way to the top.
4 Take the other end of the lace and repeat—thread it through the inside of the first free hole on the same side of the shoe. Continue all the way to the top.
Rule 21: Never match blazers with dress pants
In a blazer, white shirt, and dark jeans, you can go anywhere. You can push your kid on a swing. You can take a girl on a date. You can go on a job interview. You can drink at Le Cirque or do shots at a dive bar. You can even attend a wedding. A blazer is always safe when paired with dark jeans, gray flannels, or khakis. But DO NOT pair it with dress pants in a similar color; you’ll look like you dressed in the dark.
(Tommy Hilfiger blazer, $325, tommy.com; Hamilton Shirts shirt, $345, hamiltonshirts.com; Gap jeans, $90, 800-427-7895; Thomas Pink hankerchief, $10, thomaspink.com; Filson duffel, $225, 866-860-8906; Cole Haan shoes, $200, colehaan.com)
Rule 22: An ironed man is a wealthy man
Prosperous men don’t wear wrinkled clothes. Until you make it, fake it.
1 Set up shop
Fill your iron with distilled water. (Don’t use starch, which can damage the fibers in the shirt.) Mist the shirt with a spray bottle.
2 Go easy on the collar
Always iron the back of the collar, never the front, and avoid ironing the tips, to keep them from fraying.
3 Hit the shoulders and sleeves
Position each shoulder around the rounded edge of the board, and iron. Undo the sleeve button and spread out the cuff. Iron the inside here, too. Straighten each sleeve, smooth out any creases, and iron both sides.
4 Finish it off
Spread out the left side of the shirt’s body, smooth the creases, and start ironing. Work your way to the right side. Air-dry the shirt on a hanger for 5 to 10 minutes, so the fabric sets.
Source: Simon Maloney, head of wholesale for Thomas Pink
Rule 23: Dare to be noticed
Rule 24: Dress like you’ve made something of yourself in the world, even if you haven’t
Don’t try to look like you did when you were just starting out, Neil Strauss says. “Men stay stuck in their college style when it’s no longer flattering for their age or body,” he notes. “Let your wardrobe evolve with the times—and your title.”
Rule 25: What you can’t fix, feature
Strauss went through a long Rogaine period before deciding to shave his head. “I hid beneath hats,” he says. “Once I made the decision to shave my head, I felt so much more self-assured.”
Rule 26: When you find a look, go all in
Strauss had a buddy whose look was generic and nerdy. He had him grow his curly hair way out and wear thick black-framed glasses. “Women started treating him like a rock star because he stood out,” Strauss says.Rule 27: Match your belt to your belt loops
The guys who made your pants had a pretty good idea of what kind of belt would go well with them. If you wear a thin dress belt with pants that have big, airy loops, you will create an unfortunate sexual metaphor. So don’t do that.
Rule 28: Neither a sausage nor a sailboat be
When it comes to weekend wear, men tend to fall into one of two categories—the sausages and the sailboats. A sausage guy wears everything tight, so everything’s bulging—his belly, his junk, whatever. A sailboat wears everything loose, so every time the breeze blows, his clothes become as rippled as Jillian Michaels’s abdomen. Avoid both problems by mixing tight and loose—baggy jeans with a fitted T-shirt or tight pants with an unstructured jacket.
(Denim and Supply Ralph Lauren—a new collection launching this month—shirt, $75; fleece, $100; jeans, $90; and belt, $125, ralphlauren.com; Banana Republic scarf, $40, bananarepublic.com; Converse by John Varvatos sneakers, $145, converse.com)
Rule 29: Make a mark with your own pen
Having an elegant pen at the ready makes you look sophisticated and prepared. But it does something else that we love—it cuts down on the germs you casually pick up from those scuzzy ballpoints the waitress gives you to sign the check. (By the way, better to risk overtipping than spend time doing division in your head. So round up.) Impress your companions and prevent the flu at the same time? Works for us.
Rule 30: Bosses wear white shirts. Drones wear blue shirts
That’s why they’re called “white collar” and “blue collar.” If three men in suits walk into a room and one of them is wearing a white shirt, that’s the guy people are going to assume is the boss.
Rule 31: No Texas tuxedos
If you ever find yourself pairing jeans with a matching denim shirt, ask yourself, “Am I about to get very dirty?” If you’re slopping hogs or going on a date with Snooki, then by all means double up on the denim. Otherwise, it’s silly. Denim shirt? Khaki pants.
Rule 32: Don’t saw yourself in half
If you’re pairing light pants and a light shirt, find a light belt. Otherwise you look like the girl in a David Copperfield stunt.
Rule 33: If you want to get fit, dress fit
Coming up with reasons not to exercise is about as hard as filling out a page of Mad Libs: “The weather was too <positive adj>, my arms were very <negative adj>, and I had a <brass instrument> hanging out of my nose.” So don’t wear clothes to the gym that make you look and feel lame. No John Stockton shorts, no Loverboy sweatbands. People are looking at you. You’re looking at you. Buy a nice, well-fitted shirt that shows off your best parts and hides your flaws, and find shorts that come almost to the knee. And skip the groin stretches—do only exercises such as the pullup that look cool while you’re doing them. (I know it’s terrible exercise advice, but that’s okay. This is the style section. The guys who edit our fitness stuff never look back here!)
Rule 34: Naked guys have the right-of-way
Speaking of gyms and clothing: If two men pass each other in the locker room, the most naked guy gets the right-of-way. I would hate to accidentally hit you in the shin with my privates.
Rule 35: Dark skies? Dark clothes
Dark clothes hide raindrops and splashes better. But your best defense against bad weather is a fresh set of clothes kept in your car or office, just in case. Like, maybe, I don’t know—dark jeans, a white shirt, and a blue blazer? An extra pair of shoes and socks wouldn’t hurt either. A good soaking can ruin your look—and your day.
Rule 36: Scarves are meant to be tied
If you think scarves are little more than decoration—something Steven Tyler wears to cover up his turkey neck—then you probably don’t know the power of their insulating effect. A good wool scarf can even substitute for a jacket when temps are in the 50s. Fold the scarf in half so the two loose ends meet, forming a loop. Drape the scarf around your neck. Now pull the two ends through the loop and tighten. Onward!
Rule 37: Keep a secret grooming stash
These three items will keep you looking and feeling good no matter what your day brings.
because a man shouldn’t be shiny, no matter how much spotlight is thrown his way.
because chopping wood and fighting ninjas can dry out your mitts. After hours, you’re a tough guy. At the office, you’re smooth.
because certain proposals are better whispered than shouted.
Rule 38: Keep your t-shirt simple
Google-image George Clooney. Now do the same with Brad Pitt, Matt Damon, and Leo DiCaprio. You’ll notice something interesting: There’s not a single shot of any of these men wearing a T-shirt that says “Metallica” or “Go Badgers!” or “I’m with Stupid” with an arrow pointing to their penis. In almost every photo, if they’re wearing a T-shirt, it’s either white, black, or gray. Why? Because men look good in simple, form-fitting T-shirts. If you are wearing a logo, you’d better own the company. Or someone should be paying you to wear it. Dig?
Rule 39: Don’t be a tucker
You could say there are two types of men, Tuckers and Untuckers. It’s okay to be a Tucker on occasion, but tuck lightly—too many men shove their T-shirt into their pants in the hope that it will obscure their paunch. But such measures only accentuate one’s Galifianakis-like girth. True style falls loosely at the waist, showing a bit of belt.
Rule 40: Tailor your shoulders like a soldier
Did Teddy Roosevelt charge up San Juan Hill in a baggy tee? Did those Navy SEALs who offed OBL wear oversize jackets to make themselves look more “street”? No. Soldiers, sailors, and Marines wear clothes that square off their shoulders, not round them out. There’s no excess material to snag on some errant razor wire. That’s you, chief. This goes double when choosing a leather jacket, because you can’t change your mind and have it retailored. The jacket’s shoulders should sit squarely on yours, and not droop over onto your arms. Make sure the sleeves aren’t too long and that the bottom of the jacket hits just below your waistband. Good. Now go kill something.
(Andrew Marc jacket, $600, 888-424-6272; Rich in Clothing T-shirt, $50/pack of 3, 323-581-6000; Nudie Jeans Co. jeans, $225, nudiejeans.com; Marc Anthony boots, $120, kohls.com; Luis Morais necklace, $760, Bergdorf Goodman; David Yurman bracelet, $530, davidyurman.com)
Rule 41: A dad teaches style by example
Rule 42: Plan ahead for messes
Fresh shirts and pants for yourself and your spawn are essential if you’re more than 10 minutes away from home. Trust us.
Rule 43: Load up on pockets
Rufus Griscom finds himself favoring items with plenty of pockets for kid-related gear—binkies, face wipes, whatever. For easy access, always keep the same items in the same pockets.
Rule 44: Pack a tool kit
A multitool with scissors is something you’ll use every day. For example, cutting a few inches off the kids’ straws in restaurants makes it easier for them to drink.
Rule 45: Play up your shoulders
Throw on a sweater that has shoulder details. If you’re not blessed with Vin Diesel’s delts, a little pattern at the base of your wings can give the illusion of extra width.
Rule 46: Your pants are too short if you can see your socks as you walk
Trousers should meet the tops of your shoes with just a little break at your ankles. The exception: denim. Roll up the legs of your jeans if you want to—but only a couple of times, unless you want ankles that look like they have halos. And don’t be too neat about it. A bit of dishevelment makes it look as though you’ve been around.
(Calvin Klein sweater, $90, calvinklein.com; Denim and Supply Ralph Lauren jeans, $125, available at Macy’s; Tretorn sneakers, $65, 877-873-8676; Victorinox Swiss Army Original watch, $295, 800-442-2706; Luis Morais beaded bracelet, $225, and multicolored bracelet, $1,120, available at Bergdorf Goodman)
Rule 47: Your glasses should contrast with your face
The defining characteristic of “handsome” is symmetry: The better things seem to fit together, the better your chances of fitting together with someone else. Select eyewear that balances out the shape of your face. You’ll eliminate a visual echo and bring your mug closer to the golden mean.
Rule 48: No elastic waistbands, ever!
Sweaters and sweatshirts with elastic waistbands cause material to bag up around your midsection. This would give even Nadal a No-Deal paunch. Yet manufacturers still insist on making them. Fight back. Buy one awesome cashmere sweater this fall, and search everywhere until you find one without elastic at the bottom. The difference will blow you away.
Rule 49: Pose in clothes that match your mug
If you know you’re having your picture taken, plan ahead. Darker guys look best in whites and creams. People with olive skin look best in dark blue, dark green, black, and yellow. If your eyes are blue or green, wear a shirt that matches them. Brown eyes? Go with a color that complements your skin tone.
Rule 50: Kick the tires before you buy a cologne
The smell of a cologne when you first put it on is actually very different from what it will smell like an hour later, says Carlos Benaim, creator of some of the world’s most successful fragrances, including Calvin Klein’s Eternity for Men and the new YSL scent, L’Homme Libre. Most scents are divided into three “notes,” he explains, each a blend of oils and essences that react to your body’s chemistry. The top note is the first, fleeting part of the fragrance. It comes and goes in 15 minutes. The middle note lasts about an hour, and the base note remains for the rest of the day. “It’s important to test the fragrance on your own skin,” Benaim says. Don’t try too many at once. Instead, hit the fragrance counter first, sniff a few bottles to find a scent you like, and give it a squirt on your wrist. Do the rest of your shopping while your sample has time to evolve, and save your final decision until you’re ready to leave the store.
Rule 51: Your luggage is heading to Mumbai
Which is a bummer, because you’re just flying to Miami. Matching luggage is a waste, especially since the airline loses half of it anyway. But invest in one great-looking carry-on: A nice leather bag will scratch and burnish and age as you travel about. It will look great today; it will look better in 2021. Carry in it at least one full change of clothes that can go anywhere. Like, oh, a blue blazer, a white shirt, some dark jeans …
Rule 52: Look fitter instantly: Dress all in one color
A neutral hue, such as gray, black, olive, navy, or even white, will create a seamless line from head to toe, slimming you and making you look taller. Fuchsia, not so much.
(Calvin Klein zip up, $80, calvinklein.com; Rich in Clothing T-shirt, $50/pack of 3, 323-581-6000; Stone Island pants, $275, stoneisland.com; Raymond Weil Freelancer watch, $2,850; 800-227-7712, Will Leather Goods cuffs, $75/each, 541-434-6659; Luis Morais bracelet, $1,120, available at Bergdorf Goodman)
Rule 53: Pack jackets inside out
To prevent wrinkles in a packed suit, turn the jacket inside out and push the shoulders through. Now place the jacket in a plastic bag from a dry cleaner—the plastic minimizes friction, which causes most wrinkles. Fold it in half lengthwise, then fold it over a second time, bringing the collar down to the hem. Wrap the pants in another dry-cleaning bag and fold them into thirds. Note: The enemy of packed clothing is movement, so use the straps in your suitcase to secure your suit.
Rule 54: Toss the old stuff
Here’s the fastest way to bring order to chaos, according to Peter Walsh, a professional organizer on TLC’s Clean Sweep. Start by eliminating anything you no longer wear, and stow off-season clothes in storage bins under your bed or in totes in your closet.
Next, create a zone for each type of clothing ( jeans, shirts, suits) to easily locate everything and edit out duplicates. Finally, optimize your space by replacing bulky plastic hangers with slim, nonslip ones, and hang hooks on your door for belts and jackets.
Rule 55: Clear out the clutter
Rule 56: If you haven’t worn it in 3 years, you don’t need it
We all have items we won’t wear again. Tossing or donating them costs you 3 minutes of nostalgia. Then you’ll never think of them again.
Rule 57: Variety isn’t critical
If you have a favorite cut, color, or brand of jeans, buy five pairs. Why mess with perfection?
Rule 58: Stuff can weigh you down
As Sam Worthington notes, men move around a lot. When you’re considering buying anything, from a TV to a new suit, think about where you’ll be in a few years. Do you want to lug this with you? There’s your answer.