It can seem like there’s a lot to know about good style, and there is, at least if you want to be enrolled in its master class. But looking sharper than 99% of other guys is actually fairly simple and merely requires knowing and doing little stuff right. The kind of stuff that can be encapsulated into short, easy-to-remember principles and adages.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.