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.
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.
Then make the rest of the outfit work with them.
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 Old and out-of-date is okay, and even fun sometimes.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 know what that is, read an article like this one.
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.
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.
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.
About once a month is good.
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.
Nervous about pulling it off? Read this guide to wearing a flower with manly style.
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.
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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.