1. When in doubt: a white oxford shirt.
2. That being said, it wouldn’t kill you to mix things up every once in a while. Pinstripe shirts are good. Windowpane, too.
3. Blue gingham. Trust us.
4. The closest a man should ever come to touching denim shorts is helping a woman out of them.
5. There is a name for men who can pull off wearing sports jerseys. They’re called professional athletes.
6. ”I’m on vacation” has never been a good excuse for anything, including doing body shots, ignoring intelligence warnings about possible terrorist attacks, and wearing whatever you damn well please.
7. A rugby shirt is the most masculine thing a man can wear.
8. The 1950s and ’60s were the high points of casual. Everything before and after was hit-or-miss.
9. Fitted is good. Snug is dicey. Tight is just wrong.
10. Hemp clothes are great. If you want to smoke them.
11. Khaki pants will look and feel their best approximately two weeks before disintegrating.
12. The man who imparts opinions via T-shirt has neither the intelligence to form a cogent opinion nor the good sense to keep it to himself.
13. Small holes in jeans? Kind of cool. Small holes in sweaters? Pathetic.
14. Justin Timberlake doesn’t look quite as good as he thinks he does.
15. When purchasing jeans, leave the acid, stone, and other artificial washes to the good people of Eastern Europe. The best way to break in a pair of jeans is to wear them as often as you can.
16. The shinier the shine or the pointier the point, the less casual the shoe.
17. A discreet paint or grass stain conveys a sense of lived-in comfort. The same cannot be said for stains from food, dirt, wine, or bodily fluids. That’s just gross.
18. Denim is the center of the casual universe. And some things look better with it than others. A quick primer:
All the Time: Cotton button-down or T-shirt, brown loafers, navy-blue blazer, cashmere sweater.
Most of the Time: Crewneck sweatshirt, black loafers, tweed jacket, cotton turtleneck, white sneakers.
Only Sometimes: Hooded sweatshirt, high-top sneakers, sports jersey.
Only Under Duress: Waistcoat, silk shirt, flip-flops, necktie.
Only Under Penalty of Death: Cufflinks, suspenders, opera cape.
19. Everything looks better with age. Except for white T-shirts. Those look best new.
20. The Professor was the best-dressed man on Gilligan’s Island, followed by Gilligan, Thurston Howell III, and the Skipper. Oh, and for what it’s worth, Ginger. By God, Ginger.
21. There is nothing so wrong with one’s appearance that can’t be improved, however slightly, by tucking in one’s shirt and standing up straight.
22. Always tuck: polo and dress shirts that hang below your hip. Never tuck: sweaters and turtlenecks. Everything else is negotiable.
23. Articles of clothing that you can dress up: polo shirts, khaki shorts, blue jeans, white sneakers, and, for Texans, cowboy hats and boots.
24. Articles that you can never dress up: sports jerseys, track pants, wifebeaters, Birkenstocks, and flip-flops.
25. The only ribbed items a man should wear are socks and condoms, and he best not confuse the two.
26. A $40 pair of jeans can fit you just as well and look just as good as a $200 pair. They’ll just take a whole lot longer for you to find.
27. Cotton is the universal language of casual clothing. Wear it anywhere and you’ll fit right in.
28. Sweatpants are for sick days, couch surfing, and light exercise. For anything else, throw on a pair of jeans and get on with it.
29. Athletes inspire the best sneakers.
30. Velour: no.
31. Never wear more than two denim items at a time. Scratch that: Never wear more than one denim item at a time, and make sure it’s not a vest.
32. Michael Bastian. Tim Hamilton. Adam Kimmel. Learn these names, for they are the future of American men’s wear.
33. To our knowledge, tank drivers never wore tank tops. If they did, we might like them better.
34. Khaki is a color. Chinos are a pair of pants. Know the difference but feel free to use the terms interchangeably.
35. Any man who plays contact sports while wearing a watch he values — formal, sport, or diving — deserves exactly what’s coming to him.
36. Leather watch straps.
37. The more expensive a restaurant’s entrées, the less comfortable you will feel in jeans. Unless, of course, you could buy the restaurant, in which case you can get away with anything you want.
38. Tennis and baseball are the most influential sports on American style. Discuss.
Tennis: Lacoste polo shirts, Rod Laver and Stan Smith sneakers, tennis sweaters
Baseball: Brimmed caps, three-quarter-length shirt sleeves, flip-up sunglasses
Basketball: High-top sneakers, mesh shorts
Football: XXXL everything
Boxing: Boxer shorts
39. No one you work with should ever see your toes or your nipples. Please dress accordingly.
40. Remove the brass buttons from your store-bought sport coat and replace them with buttons from a fancy golf club. It will annoy the hell out of the club’s (real) members.
41. The button fly is:
a) total bullshit.
b) the latest battle in the decades-old war between the all-powerful zipper and button industries.
c) a way to avoid tearing up your johnson.
d) all of the above.
42. Animals make the best logos.
43. For bomber jackets, brown; for biker jackets, black. Deviate at your own peril.
44. Dress not like Kanye West. That goes for you, too, Kanye.
45. Before you buy a cashmere sweater, touch the fabric and then rub your fingers together. If it imparts any residue or feels slippery, that’s a sure sign of bad or even fake cashmere. That and the forty-nine-dollar price tag.
46. There’s a 74 percent chance that a man who isn’t wearing socks isn’t wearing underwear, either. Both endeavors attract the same kind of man.
47. Don’t borrow any clothes from that man.
48. The best jeans have five pockets. The best khakis have four. Anything more or less and you’re asking for trouble. Oh, and 1998 called: It wants its cargo pants back.
49. Unless you’re wading into water or modeling for a catalog, there’s never a right time to roll up your pants.
50. Unless he’s a chef, a gardener, or a jolly fat man from Holland, no one should ever wear clogs in his daily life. Same goes for Crocs.
51. Speaking of: We’re not sure what Americans did to deserve Crocs, but whatever it was, we’re sorry. We’re really, really sorry.
52. If you see the words “Barbecue,” “Come as you are,” “Bring the kids,” or “BYO” on an invitation, dress casually. When in doubt, bring a navy-blue blazer.
53. Or a cardigan. A cardigan works, too.
54. The greater the number of exclamation points on an invitation, the more casual you can dress.
55. Unless he’s headed to a black-tie wedding, a man always has options.
56. Even casual style demands good shoes. But not all shoes are equally casual.
57. Unless you’re wearing a blazer, there’s no wrong time to roll up your sleeves. How high you choose to roll them says a lot about you.
58. The solid blue button-down shirt is the Jay Leno of American style.
59. There are worse things in the world than being known as the guy who always wears a blue button-down. Like being known as the guy who looks like he just rolled out of bed or the guy who always smells a little funny. If you’re going to settle on a look, get it right.
60. The baseball cap is America’s greatest contribution to headwear. Runner-up: the cowboy hat.
61. Berets: no. Not in Paris, France, and especially not in Paris, Texas.
62. The overlap between active sportswear and casual party attire should be kept to an absolute minimum. Leave the neon shirts and pants for the links, the white tennis shorts to the courts, and the swimsuit at the pool.
63. There’s no harm in letting yourself go, so long as you’re never more than an hour away from pulling yourself together.
64. A hood knocks ten years off your age and twenty points off your IQ.
65. Sunglasses don’t belong on top of your head, folded into the neck of your shirt, or hanging around your neck by some nylon cord. If you have to remove them, hold them or put them on a table.
66. A man of style never discusses the cost of his clothing, even if that fourteen-dollar sweater was a total steal.
67. We’re all for comfort. Just make sure the damn thing fits.
68. If you’re on the shorter side, vertical pinstripes help stretch out your legs.
69. There’s not a whole lot of room for irony or imitation in style. The best-dressed men always dress like themselves.