23 Rules for Dressing

If you forget everything else, remember this. Wear clothes that fit.

1. Be identifiable unless you are doing something that requires you to blend in. Notice. Unless your everyday involves eavesdropping or other clandestine behavior, this is largely every time you leave your house.

2. Good pieces of clothing often fight with you. The first time you put them on, you are going to be want to be doing your thing and it is going to be pulling you in a different direction. This is a good thing. A good piece of clothing has character, and likely you are going to wrestle with it before you get onto the same wavelength. These always end up being the best garments.

3. Wear clothes that fit. If you are a adult American male who doesn’t put much thought into these things, you probably need to go down a size. What you really need to do is seek guidance from a friend.

4. Finding jeans that fit may be a nightmare. Keep looking.

5. The salesperson is not your friend, especially if they make commission.

6. Avoid being a billboard. Your clothes advertise you, not Banana Republic. That North Face logo looks trashy.

7. You wear glasses on your face. You wear them all the time. Buy glasses that look good on you.
7a. If there is exactly one place where you should spend an extra dollar on apparel, it is your glasses. You do yourself no favors by being seen in awkward glasses.

8. Be careful about loud prescription glasses, especially if you are on a budget. You need a personality to back up loud glasses day in and day out.

9. Tennis shoes generally have color accents. You need to not ignore these. My new balance sneakers are black and white with red accents. This red needs to match, complement, or contrast something else, preferably between the knees and neck.

10. Keep a wide variety of colors to wear, especially in springtime. These clothes provide you with tools to match other colors during all the other seasons.

11. Don’t be afraid to wear white indoors out of season. It needs to be clean. It needs to be done tastefully.

12. Keep a pair of black dress shoes. They don’t have to be the most comfortable thing around. I personally like a sole that clacks when it hits a hard surface, it reminds me I am dressed up for a reason.

13. Worn dress shoes have extra character if they are still shiny. It means you have been wearing them properly, at events that they don’t get dirty.

14. Any regular use shoe needs to be chosen for comfort. If you can’t find a shoe that provides comfort yet looks halfway decent, go the $30 wal-mart route and wear them out in 3 months. I’ll go through a good pair of $120 shoes in 12-18 months. I will not again buy $100 stylish everyday shoes that I intend to take the distance and get home day after day with hurt feet. I’ll just wait.

15. Finding acceptable shoes may be a nightmare. Keep looking.

16. Don’t wear jeans that advertise that you sit at a computer all day. The calves of people who sit all day have no curvature. If you have calves, you can wear skinny jeans. No calves? No skinny jeans. I don’t care if you look like a hipster, just don’t look like a worthless hipster.

17. Something above your knees needs to match your hat.

18. Something below your neck needs to match your shoes.

19. Hat-Belt-Shoes is a solid combo.

20. Notice how a vest also meets both criterea, and has the added bonus of softening the heavy effect that a long sleeved shirt has.

21. Your backpack is part of your outfit.

22. Change with the seasons.

23. Break any of these rules occasionally, with the exception of the glasses. You wear them on your face.

Gabriel’s rules for hats coming soon!