51. YOUR NECKTIE AND POCKET SQUARE CAN SHARE A COLOR FAMILY, BUT THEY SHOULDN’T BE A PERFECT MATCH
They don’t even have to share colors — the square could complement a color from the shirt or jacket instead.
52. SOMETIMES LESS IS MORE
A couple plain, dark solid pieces with one bright accent can do more than a flashy, patterned suit or shirt.
53. THEN AGAIN, SOMETIMES MORE IS MORE
Go over the top with color and pattern once in a while — maybe when you have something to celebrate, or just when you’re in a really bouncy mood. But don’t make a habit of it.
54. KEEP THE TOP AND BOTTOM BALANCED
If you’ve got a sleek, streamlined jacket and a simple shirt, don’t wear big, fuzzy pants with lots of texture. Similarly, don’t pair a cable-knit sweater with ultra-fine wool slacks. Stay consistent all the way up and down.
55. WEAR SEASONAL COLORS
Dark earth tones and shades in autumn, grays and blues in winter, colorful pastels in spring — you get the point.
56. FIND AN OUTDOORS JACKET THAT YOU REALLY LOVE
Leather, wool, cashmere — doesn’t matter. Something beloved that you can wear from the first cool days of fall on up to winter parka season, and again in the spring.
57. BROWN OR BLACK LEATHER — PICK ONE
They don’t all have to be identical shades, but you shouldn’t be rocking a black watchband with a brown belt or anything like that.
58. IF YOU WEAR SUITS IN THE WINTER, WEAR A LONG WOOL OVERCOAT
Anything short enough that you can see the bottom of the suit jacket poking out beneath the hem of the coat doesn’t make the, ahem, cut.
59. DON’T BELIEVE IN ABSOLUTE RULES
White trousers after Labor Day. Plaids with stripes. You’re told not to do them, but there’s always a reason to break a rule once in a while. Don’t be afraid to. But remember that the “rules” are usually there for a reason, too, and use some common sense.
60. OVERDRESS
There’s nothing wrong with being the best-dressed guy in the room. Be aware of social norms — don’t wear a three-piece suit to serve meals at a soup kitchen or something — but in general, plan on looking nicer than other guys in your social group at any given gathering.
61. LEARN A NEW NECKTIE KNOT
Heck, learn a dozen. Some are convenient, some are fancy, and a few are both. Know your favorites.
62. LAUGH AT TRENDS
They’re a way to separate style illiterates from their money. Keep your look timeless. Trends can be a fun inspiration if they appeal to your existing sense of style, but don’t pursue them just because they’re “in.”
63. IF THE DESIGNER’S LOGO IS VISIBLE, IT’S NOT AS STYLISH AS YOU THINK
See previous point about trends and add some emphasis. You’re nobody’s billboard. No visible brand names.
64. PAMPER YOUR SKIN
Get some good skin cream and use it. Find the product that solves your particular problems whether that’s oily skin, dry skin, or something else entirely.
65. PAIR A NICE SUIT WITH SOME COLORED CANVAS SNEAKERS
Rockstar.
66. OWN ACCENT PIECES
Scarves, hats, jewelry, funky shoes, weird belts. Get some unique items and use them whenever an outfit looks okay, but boring. Thrift stores, eBay, and Etsy are all great sources for these.
67. BACKPACKS ARE FOR SCHOOL KIDS
If you’re not going to class right this minute, trade up to a messenger bag or a briefcase. For that matter, trade up even if you are in school.
68. SUNGLASSES ARE PART OF YOUR LOOK AS SOON AS YOU PUT THEM ON
Own a couple pairs in a couple different styles — you’ll end up needing them as you vary your look.
69. KEEP YOUR JACKET BUTTONED EXCEPT WHEN YOU SIT
The taper toward the waist is half the point of a jacket. Don’t lose the effect by going unbuttoned.
70. ON THAT NOTE, THE BOTTOM JACKET BUTTON ALWAYS STAYS UNDONE
Close the top button on a two-button coat, and either the middle button only or the top two buttons on a three-button coat. There are other looks, and someone’s always trying them out, but these will always be right.
71. YOUR OUTFIT IS ONLY AS GOOD AS THE CLOTHES IN IT
At the end of the day, you can’t look like a runway model in clothes from Walmart. Be prepared to spend at least a little money if you want to look really good.
72. FIX DAMAGES SOONER, RATHER THAN LATER
Missing buttons, fraying edges, torn seams — get them to a tailor and get them fixed. No excuses. Wear and tear looks terrible in public.
73. CASUAL LEATHER SHOES MAKE ANY EVERYDAY OUTFIT LOOK MORE STYLISH
Have some good brogues, saddle shoes, or loafers for your day-to-day get-ups.
74. DON’T OVERTHINK IT
If everything fits and the colors aren’t an obvious clash, your outfit is probably presentable at the very least. The rest is just details.
75. KEEP YOURSELF WELL-GROOMED
Trim your nails, shave regularly and with care, brush your teeth. A raggedy body under nice clothes jars the eye (and looks gross).
76. SHIRT CUFFS SHOULD BE VISIBLE PAST THE ENDS OF YOUR JACKET SLEEVES
“A half inch of linen” is the old-fashioned rule of thumb. Don’t obsess about it too much but show at least a little shirt cuff.
77. TIES CAN BE FUN
Paisleys, variegated stripes, figure patterns, knits — mix it up. Look for textures beyond basic glossy silk (or synthetic) and for varied colors.
78. PINSTRIPED SUITS ALWAYS LOOK BEST WITH PLAIN WHITE PINSTRIPES
There are other options out there, but none are as timeless and sublime as the plain white pinstripe on a dark charcoal or navy suit.
79. YOUR CELL PHONE IS PART OF YOUR STYLE THESE DAYS
Get a case and make that case something that works with your basic tastes. Fun is good; so is slim. The less of a bulge in your pockets, the better.
80. YES, YOU CAN WEAR A DOUBLE-BREASTED JACKET
It can even be a blazer, rather than a suit jacket, so long as you keep the trousers and shirt conservative. But don’t you dare wear that double-breasted jacket unbuttoned.
81. WEAR THE LIGHTEST FABRICS IN THE SUMMER
If you don’t own at least a few pieces in lightweight linen or seersucker, you’re torturing yourself needlessly.
82. VISIT A MENSWEAR STORE YOU’VE NEVER BEEN TO BEFORE
See what you like. You never know.
83. THE MAN PURSE IS NEVER GOING TO CATCH ON
If you’ve been waiting for everyone to wake up and realize how stylish yours is, stop.
84. JEANS CAN SIT ON YOUR HIPS. EVERYTHING ELSE GETS WORN AT THE NATURAL WAIST
85. THE SHINIER YOUR SHOE IS, THE DRESSIER IT IS
Assuming we’re talking about leather dress shoes, a higher gloss is dressier, while a softer texture is more casual.
86. BOW TIES DON’T JUST COME IN BLACK
Wear a patterned one in place of a regular necktie some time.
87. TIE YOUR NECKTIE SO THAT THE TIP TOUCHES THE TOP OF YOUR BELT
A little longer is okay; shorter is not.
88. YOUR OFF-DUTY CLOTHES STILL GET LOOKED AT
Swimwear, pajamas, workout clothes — someone’s going to see you in them eventually. Buy ones you look good in and replace them before they wear out.
89. FACIAL HAIR NEEDS TO LOOK DELIBERATE
You can have a full beard if you really want one but shape the edges with a razor so that it doesn’t look like you’ve just let it grow. You want people to think you’re making a statement, not being lazy.
90. YOU WANT PEOPLE TO NOTICE YOUR FACE
Wear clothes that guide the eye upward toward your chin and mouth. There’s a reason classic menswear tends to open upward (think about collared shirts and suit jackets).
91. IF YOU MIX PATTERNS, VARY THE SCALE OF THE PATTERNS
Small checks with wide-spaced stripes — no problem. Big checks with big stripes — problem.
92. DRESS THE BODY YOU HAVE, NOT THE BODY YOU WANT
It’s great to be working towards a fitter physique, but don’t look like a total schlump until you get there.
93. HAVE ONE OR TWO BIG, SOFT FLANNELS OR CARDIGANS FOR COOL NIGHTS
Half the time you’ll end up giving these to a girl to wear when she gets cold — and that’s just fine.
94. ORGANIZE YOUR WARDROBE
Make it easy to reach in, grab any couple of items, and have an outfit that works. That means finding a home for the less-stylish utility pieces that’s far away from your good clothes.
95. NEVER LET A WOMAN PLAN YOUR OUTFITS
Even fashionable women are working with a different stylistic language from you. Unless one or both of you are cross-dressers, don’t make a habit of taking regular style advice from a woman.
96. PANTS BEAT SHORTS, EVEN IN HOT WEATHER
Shorts cut the leg in two; a pair of lightweight linen, seersucker, or cotton pants will create a sleeker, more put-together silhouette, and always look better than shorts, while only being slightly warmer to wear.
97. IF YOU LIKE A STORE, SUBSCRIBE TO THEIR E-MAIL LIST
Yeah, you’ll get advertisements that you don’t want. But you’ll also get sales and coupons that you will want, and that they don’t offer anywhere else. If you limit yourself to two or three of your top favorite brands, it’s well worth the inbox clutter.
98. REALLY GOOD DRESS SHOES MAKE A BIT OF NOISE WHEN YOU WALK
Don’t be shy about it. Embrace the authoritative tap-tap-tap of stacked leather heels.
99. RESIST THE URGE TO CORRECT PEOPLE’S STYLE
Even when you know they’re doing something wrong. They’re not going to take it as a kindness no matter how sweetly you say it.
100. THERE ARE WORSE FATES IN LIFE THAN DRESSING LIKE SOMEONE’S DAD
Or even someone’s grandfather. The generations before us knew a thing or two about looking sharp.
And most important of all…
101. NEVER WEAR A BAD FIT!
Ever. If it isn’t a close, flattering fit with no pinching or sagging, don’t wear it. This is the ultimate rule for looking good. Seriously. If you’re going to take one thing away today, take this one.
