50. A warm iron and a can of spray starch can do wonders. Invest in them even if you don’t wear slacks and button-ups regularly.
49. “If you buy one pair of shoes and one suit per year, you’ll have a nice collection soon enough. It’s an investment. Also, know your measurements and sizes, because you might find a woman who wants to hook you up and get a suit made.”—Chris Mathis, 36, barber
48. Wearing a fitted hat on your commute to work with your business suit or with just pants and a dress shirt isn’t a good look.
47. “Tone down the bagginess a bit without wandering into nut-hugger territory. Showing your ass and boxers is not appealing in any setting.”—Anslem Samuel, 31, magazine editor
46. Find a good tailor.
45. T-shirts should fall just below your waist, and the seam of the shoulder should be right on your shoulder.
44. Wear a belt. It’s called underwear for a reason.
43. Don’t try to outdress a woman. She should be the center of attention and should not feel that she’s underdressed.
42. “The world is bigger than your hood and the places your favorite rappers represent. Try to travel to a place where your cell phone won’t work. That’s when you know you’ve actually gone somewhere. If you can’t afford to put your passport on pivot, try reading a book or travel guide about the place you’d like to visit.”—A. Samuel
41. Barnes & Noble should be your best friend.
40. “[As far as books], start with the classics: Catcher in the Rye, The Count of Monte Cristo, The Odyssey, Crime and Punishment.”—Q-Tip, 38, rapper/producer/actor
39. If reading books the size of War & Peace seems daunting, peruse different types of magazines—ones covering art, architecture, design or photography.
38. Try not to go straight to the sports section of the newspaper.
37. Watch the news, preferably more than one channel. Suggestions: BBC, MSNBC, CNN and, yes, even FOX News.
36. Being open-minded and aware of the world around you shows class and sophistication, but avoid seeming pretentious by being modest instead of showing off what you know.
35. “There will come a time when you outgrow the dudes you grew up with. Have a beer with them once in a while, but it’s OK to move on and be friendly with new people.”—Adam Matthews, 36, journalist
34. Go easy on the slang, especially among those who are already judging you based on race and age.
33. Don’t just talk the talk.
32. Look people in the eyes when you greet them and shake their hand.
31. “Take criticism with an open mind. You can improve from listening to superiors and by changing your actions to serve them. Don’t mess with the pack order—it’s there for a reason.”—A. Matthews
30. Be on time to meetings—early if you can.
29. In meetings, don’t hold conversations at the same time someone else is speaking. Let the person finish his point before giving yours.
28. “Memphis Bleek had one good line: ‘The strong move quiet, the weak start riots.’ Don’t be the guy who always needs attention on him or starts problems over small stuff.”—Mark Rooney, 31, salesman
27. Don’t talk down to coworkers, including subordinates. You may be above them in rank, but as a human being, you’re on a level playing field.
26. “Look for the people who will make your job easier. You can’t do everything yourself, so you’re going to need help. These people will be pivotal to your success. And always thank them and show your appreciation when they come through for you.”—Claveria “JoJo” Gumersindo, 36, quality management
25. Don’t be afraid to share the spotlight in your workplace. Rather than being self-centered, work together with somebody of equal ambition. You don’t always have to be in the front seat—the backseat is cool.
24. Don’t think because someone has money, he’s a good businessman; there are people with no money who are better.
23. “You don’t want to do anything and everything just for a buck. I’ve walked away from deals a number of times that I think were good deals, but I didn’t think they were good people.”—Grant Hill, 35, Phoenix Suns small forward
22. Learn more about food and where to eat it cheaply. Most cities have great ethnic food; you just have to go to a specific neighborhood to get it.
21. If you initiate a dinner date or meeting, then you should expect to pay. That works both ways.
20. At a restaurant, let women order food first, and stand up when a woman leaves the table.
19. Avoid unnecessary use of expletives in public, especially in the presence of a woman you’re trying to impress.
18. Unless your Fight Club membership is in danger of being revoked, walk away from altercations.
17. Always put your napkin in your lap at dinner. Stuffing it in your shirt is grounds for getting slapped.
16. Caveman behavior at the dinner table isn’t good. Use utensils, avoid chewing with your mouth open and don’t leave a messy plate.
15. When eating out, always tip more than 20 percent. Waiters live off of customers’ kindness. And you don’t want to make other people at your table reach into their pocket to cover your cheapness.
14. “Treat older women as if they were your own mother.”—C. Mathis
13. Always have a woman walk on the inside of the sidewalk and on the side of parked cars in a parking lot, basically using your body as a barrier from harm.
12. Sometimes the best movies are in the independent market. Documentaries are great educational sources, too.
11. If you’re trying to have a relationship, let the woman know. If you’re not, and you’re just trying to hit, let them know that, too.
10. Brush your teeth, gargle or have a breath mint before getting up close and personal.
9. If the opportunity presents itself on the first night, don’t pull a condom out of your wallet. She’ll get the impression that you’re premeditated and will be turned off.
8. Even if you’re having a one-night stand with a woman, be respectful. Jay-Z might brag about kicking women out five minutes after having sex with them, but he’s not having sex with your date—you are. Casual sex needn’t be disrespectful. In fact, it’s more fun when its not.
7. “Don’t fall asleep when you’re done. Just because you got yours doesn’t mean the night is over.”—JoJo
6. “If you’re not into oral, you better get into it. Not with every woman, of course, but someone you’re serious with.”—C. Mathis
5. “If you want her to be your devil, treat her like an angel.”—Gerrell Gaddis, 32, songwriter
4. Don’t ask about the last guy she was with; as in, “Was I better than he was?” Being competitive is a young man’s game.
3. Never forget to introduce your woman as your girlfriend, spouse or otherwise to people when you’re out at functions together.
2. Avoid public fights with your woman. Keep things private to let her know there’s an exclusive world that you and her share.
1. “Young guys should pump their brakes. Don’t have kids until you’re 30, and look at her family and background to know what you’re getting into.”—C. Mathis
