Below you’ll find the best of the best of such tips: a hundred things (plus one extra) that you can be doing, right now, to make yourself look sharper. You can thank us later.
1. Throw out or give away anything you haven’t worn in over a year.
You get two “beloved old favorite” exemptions here, as well as formalwear. Ruthlessly pitch or donate the rest.
2. Get everything adjusted.
Well, okay, not everything. But most things: nice pants, shirts, and jackets should all go to the tailor for adjustments, unless they came custom-tailored already.
3. Spend more money on less pieces of clothing.
Quality lasts longer than quantity, and you look better in it.
4. Shop for a suit in person.
Even if you don’t need one. Just get the experience of comparing jacket styles, fabrics, and cuts.
5. There are more shoe colors than brown and black.
Colored leather and suede are fantastic shoe options. Get a little crazy with reds, blues, and grays. Don’t worry about matching a belt to each one — a black belt with gray shoes or a brown one with oxblood red is fine.
6. Trouser cuffs should “break” on the tops of your shoes.
That means they rest very lightly on the leather itself. You shouldn’t have a gap between your pants and your shoes.
7. Wear a pocket square.
Any time you’re wearing a jacket. No exceptions.
8. Buy something in a pattern that occurs nowhere else in your wardrobe.
9. Next time you go to put on jeans, grab a pair of slacks or chinos instead.
10. Belts or suspenders — pick one.
Never both at the same time.
11. Wear a necktie when you don’t have to.
Just for fun.
12. Watch any movie starring Cary Grant.
Now ask yourself: “What can I do to dress a little more like that?”
13. Gym shoes are for the gym.
Ditto athletic socks.
14. Wear a lightweight sweater under a sports jacket with some jeans.
Doesn’t that look good?
15. Get a pair of colored trousers.
Something funky. Red, green, yellow, orange, whatever.
16. Go read a book on style.
Or a magazine. Or an article. Something about fashion. Old and out-of-date is okay, and even fun sometimes. Just get exposed to something new.
17. Match the color of your socks to the color of your trousers.
Most of the time. When you want to be daring, wear a bright, contrasting color instead.
18. Have a removable top layer.
In the dog days of summer, you can go with one shirt. The rest of the time, have at least two presentable layers on top. You never know when you’ll want to loan a lady your jacket/shirt/whatever.
19. Invest in a really nice suitcase and day bag.
Your luggage is part of your style.
20. Shop with a friend.
Sales people are paid to sell you things whether they look good or not. Take a friend who’ll tell you to your face when you look like an idiot.
21. Own a watch you can wear with a good business suit.
Handsome. Functional. Classic. It’s amazing how such a small accessory can greatly enhance how you look and feel.
22. Understand contrast.
It will help you get the right amount in your outfits. If you don’t understand, read up on “understanding contrast”.
23. Own more shoes.
How many pairs do you own? Get some more. Vary the styles. Shoes are the most underrated tools in a guy’s style arsenal.
Read up on the 3 types of shoes every man needs.
24. Traditional light blue denim is a great color for jeans…
…if you’re building houses or ranching cattle. Otherwise, get a dark indigo instead of light blue, or go with a different color entirely.
25. Take your measurements.
Write them down and tuck them in your underwear drawer or something. They always come in handy when you’re shopping.
Read up on how to accurately take your measurement.
26. Check the size of your favorite pieces of clothing.
Those numbers are worth writing down too. If a shirt fits perfectly, you probably want your other shirts in about that size as well.
27. Always dress like you might decide to drop by a restaurant or nightclub with a dress code.
Because you might. And even if you don’t, you might as well look like a guy who’s got plans.
28. Practice rolling up your shirtsleeves a bunch of different ways.
Do you like a fat roll? A thin one? Tall, short, rumpled, crisp? Play around with it.
29. Flip through a slideshow of images from a men’s fashion show.
Nine-tenths of the things you see will be way over the top and useless to you. Use the other 10% for inspiration.
30. Head to a thrift store and buy every sports jacket that fits you…
…and costs less than $20. Okay, maybe not every single one, but at least four or five. Even the weird ones. You’ll use them.
31. Button-down collars aren’t business dress.
Yeah, you’ll see guys wearing them with suits. Don’t be those guys. A business suit deserves a business collar, and that means no buttons at the tips.
32. Shine your shoes more often than you think you need to.
33. Wear a boutonnière in your lapel.
Not for a wedding, and not with a tux. Just for fun some day. Any old suit or sports jacket will do.
34. Put some product in your hair.
If you already use product, try a different kind of product.
35. Iron your own shirts.
It’s a useful skill for traveling, and it’ll save you money at home.
36. Get some dress slacks without belt loops. Then wear ’em with suspenders.
37. Don’t wear T-shirts with graphics on them…
…for anything that isn’t housework, a workout, or a rock concert. Upgrade to a solid-color tee, or another lightweight option like a henley or polo.
38. Try a decorative lining.
Suit and sports jackets sometimes come with them; as do some dress shirt cuffs.
39. Wear jewelry.
Not every day, and not always the same piece. But a ring here or a necklace there is great.
40. Have two nice white dress shirts.
Be sure they’re free of stains and wrinkles, ready to go at all times. They go with everything.
41. Try wearing cologne.
You can get small testers from most department stores. Try a few and see what goes well with your natural scent.
42. Clean your wallet out regularly.
The slimmer it is, the less wear and tear on both the wallet and the pocket it’s shoved into. It’ll also look nicer when you pull it out to pay for things.
43. Wear a scarf.
Not just because it’s cold outside, but also as a fashion accessory.
44. Expand your belt collection.
The easiest way is to own belts that can snap open for interchangeable buckles, and then to hit the internet looking for vintage buckles — that way you’re only buying two or three pieces of leather for dozens of looks.
45. Own at least one dark business suit.
Then, if you can afford it, own one lighter social suit as well.
46. Use patterns to flatter your body type.
Grab broad checks to add a little weight and breadth, or use light vertical stripes to add height and slim down your appearance.
47. Live it up a little.
Wear that Hawaiian shirt or those bright red pants once in a while. Nobody needs to be the textbook timeless gentlemen every day of his life.
48. Get your jackets pressed.
Light, unstructured ones are particularly prone to wrinkling, so press ’em early and often. Rumpled backs ruin the whole look.
49. Gold or silver metals — pick one.
Your wedding band is an exception. But other than that, keep it to one kind of metal.
50. Clean your clothes regularly.
Launder the things that can be; take what can’t to the dry cleaners. Brush wools off to keep them from pilling and gathering fuzz.
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, denim — doesn’t matter. Something battered and 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 ’em, 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.
Know the “Sometimes, Always, Never” rule.
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 ’em into a tailor and get ’em 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. Funky 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 orseersucker, 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 other 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. NEVER WEAR A BAD FIT.
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