Fathers have an obligation to pass on what they know to their sons. As you boys get older, I wanted to give you some rules about how to properly dress for occasions that require more thought than blue jeans and a t-shirt. I started thinking about this the other day when one of you asked me why I dress up for work. His question was not a bad one and no child can be aware of that which he is not taught. Therefore, while you boys are all still in “student mode”, it is probably not too early to explain proper dressing for men so that you at least know how to dress properly when the situation calls for more thought about what to wear. I don’t expect you to dress this way now but as you get older and get jobs or attend more formal social events, you should at least know some basic rules. So with no further ado, here are Dad’s 44 rules of proper men’s attire.
1. Don’t ever judge anyone else by what they are wearing. In the larger picture, clothing is merely superficial. You don’t know the knowledge, circumstances or resources of others and should never look down on anyone based on appearance. I am giving you these rules because society does, unfortunately, judge by appearance and I want you to at least know what is proper. This doesn’t mean you necessarily have to follow these rules. I just want you to know what they are so that if you are trying to dress up to make a good impression, you will know what you are doing. However, you should never judge others.
2. The reason for dressing appropriately is that it is simply good manners. You are showing respect for those with whom you come in contact. As a lawyer, people expect a professional look because they are coming to me as an expert to help them deal with important issues in their lives. It would be disrespectful of me if I dressed informally when I am working. It would send my clients the message that I did not take their matter seriously. I always want my clients to not notice how I am dressed, just to think I am dressed professionally and appropriately.
3. Appropriate dress depends on the circumstances. Always dress sensibly. If you are a farmer, you wear sturdy, weather appropriate clothing. If you work in an office, you dress differently. After a foot of snow, you wear boots, even if you work in an office. You may wear overshoes or change into dress shoes in the office but there is nothing sensible about trudging through a snow bank in loafers.
4. Pay attention to your shoes. Other people, especially women, do. True dress shoes tend to be more expensive but last longer, look better and are often more comfortable. Dress shoes shine and are capable of being shined. Keep them clean and polish them on occasion. Traditional casual shoes are better than fake dress shoes which look like fake dress shoes almost immediately. Dress shoes are required for suits and a good choice for sport coats and trousers. Casual shoes such as loafers and bluchers are fine with chinos, corduroy and jeans.
5. With shoes, you generally get what you pay for. Buying cheap never pays off over time. True dress shoes are black and brown cap toe Balmoral. These shoes are smooth, shiny and lace up. Shoes with brogue, boat shoes, loafers, bluchers and chukkas are fine but are not dress shoes and not to be worn with a suit.
6. Wear natural fibers. Men’s suits are made of wool. The best trousers are also made of wool. Ties are made of silk. Dress shirts are made of cotton. Linen, hemp and rayon are other natural fibers. Natural fibers look the best, are the most comfortable and generally are used in the better made garments. Avoid synthetics for business or formal wear. Synthetics breathe like a corpse and never look sharp. Companies that make clothing with synthetics are usually also cutting corners on quality. Shoes are made of leather.
7. A good choice for a nice first set of clothing is a navy blazer, charcoal pants, Oxford shirt (white) and brown dress shoes.
8. Always go for a classy, timeless look. Never chase the latest fashion. Dress conservatively and you won’t go wrong. Never be gaudy in your attire.
9. A good first suit would be a gray or navy blue solid. Gray is a true neutral color, looks good on everybody and goes with almost anything. Black is less traditional and harder to coordinate. Black suits with white shirts also tend to wash away the face of a fair skinned person. Charcoal may not seem that much different than black but it makes a world of difference. If you get a black suit, wear a colored shirt. This violates later rules but is the right thing for Scandinavians to do if they wear a black suit.
10. Solids are more formal than stripes or patterns. This goes for shirts as well as suits.
11. White solid shirts are the dressiest. Light blue is next. Any other color or pattern is fine but just know it is less dressy.
12. A good staple shirt is an Oxford. These shirts are technically casual and do not go with suits because the collar buttons down. However, they go with sport coats.
13. There is no such thing as a short sleeved dress shirt.
14. Never wear a tie unless you are also wearing a suit or sport coat. I know guys do this all the time and its the norm for basketball games. I won’t yell at you or judge you. Just know it is not the right thing to do when you get older. It is ok to remove the suit coat or sport coat but not to skip it altogether.
15. Button down shirts are more formal. Woven is more formal than knit. Collared shirts are more formal than non-collared. Long sleeves are more formal than short sleeves. White is more formal than color. Solid more formal than patterned or stripped.
16. Wool trousers are preferred over anything else. As a young man you can skip pleats if you want to. If you get pleats, also get cuffs. Trousers should have a break. This means the back comes down to the top of your heal and the front breaks a bit on your shoe.
17. Never let your girlfriends pick your clothes to buy. Listen to their advice but they don’t know the rules for men. They know the rules for women. They know a lot more about clothing in general but unless their Dad knew how to dress like a gentlemen and explained these rules to them, they don’t know how you should dress because the rules are different for women.
18. Never let the store clerk pick your clothes. Get the clerk’s advice if you want it but remember who they work for.
19. Except when you are just starting out, anything you buy should match at least three other things you already own.
20. Your goal is not to have a bunch of stuff hanging in your closet but to have versatile clothing. You can wear the same navy blazer several times a week by wearing different trousers or a different tie.
21. Never wear the same shoes two days in a row. Put shoe trees in at the end of the day and wear a different pair tomorrow. Your shoes will last much longer if you let them dry and keep them clean.
22. Have and wear tan chinos at times but don’t be the guy who wears them every day with a blue shirt and maybe a tie. You will look like every other entry level employee who doesn’t know how else to dress.
23. A suit coat or sport coat must fit properly in the shoulders. Otherwise don’t buy it. A coat is meant to flatter the male figure and should taper in at the waist from the broadness of the shoulders. Don’t get a coat that is too long or that has sleeves that are too long. You’ll look like a kid trying to play dress up with your father’s clothes and you will look sloppy. A bit of “linen” should show past the coat sleeves. This means about a quarter to half inch of your shirt should extend beyond the sleeves. The coat length should cup in the middle joint of your fingers.
24. A suit or sport coat is always dressier than a sweater and more flattering in appearance.
25. Match your socks to your pants.
26. Match your belt to your shoes. Brown shoes, brown belt. Black shoes, black belt.
27. Always wear a tie with a suit. Ties are optional with sport coats. Sport coat and no tie is way better than tie but no coat.
28. Don’t wear a short sleeved shirt with a tie. You’ll look like you should be stocking shelves in a grocery store.
29. Without going overboard, the pockets in a coat are meant to be used and are great for a cell phone, pen and so on.
30. I know fedoras are out of fashion but a well-dressed man dresses sensibly and there is nothing more sensible than a fedora in wind, rain, cold and to keep the sun out of your eyes. Baseball caps etc don’t go with business attire.
31. To start off, have tan, gray and navy wool trousers. Wool always looks nicer than cotton or synthetic and is more breathable and comfortable.
32. Wear 100 percent silk ties. You can have fun here with colors and patterns. As a country lawyer, I avoid pocket squares, French cuffs and such as too affected (over the top, foppish). I am not trying to distract people or say “hey, look at me”. I am trying to be respectful. However, colorful ties are fine.
33. Dress socks go over the calf. Crew length socks sag, look sloppy, and it is considered bad form for a gentleman to show leg.
34. True dress shirts (to be worn with suits) do not have buttons on the collar. I love my Oxford shirts with their button down collars but technically they are considered casual. They are fine with a sport coat but not with a suit. Stick with solid white pointed collar shirts with your suits.
35. No color is more versatile than charcoal gray. Navy and tan are next.
36. Your goal is not to spend too much on clothes but to have classic, versatile pieces that you can mix and match. You get what you pay for. Buy for quality, not price. The best way to do this is to follow rule 19 above and to look for sales rather than buying for an event when you are at the mercy of the store’s current pricing and availability.
37. The most expensive item in your closet is the one you don’t wear, not the item you paid more for but wear a lot because it looks good, is comfortable and is versatile. Don’t buy on a whim.
38. Break these rules once in a while. I just want you to know what is proper, not to make you a slave to clothing rules. An occasional fashion faux pas is not the end of the world.
39. If you can’t quite tell by now, it is better to have fewer, timeless pieces than too much clutter that seemed like a good idea to the store clerk or your girlfriend. Your life will be simpler and less expensive if you follow these rules when you get to the point in your lives that you need to dress for an office or more formal social setting. If you go into careers that don’t require this kind of dressing, that is fine. Wear clean, sensible, good quality clothing that will last and take good care of it.
40. Loose, baggy clothing is not the answer. You may hear that looser clothing makes you look thinner and better. That is not true. Baggy clothing makes you look sloppy. Clothing should fit your figure. This means that it should not be too tight. Clothing should not bulge and buttons should not be stressed. I just mean that being properly dressed means wearing clothes that fit.
41. If cash is tight, and it will be at times, buy cheaper shirts and always wait for sales on everything else. I don’t think I ever buy a suit or sport coat at full price. Don’t skimp on shoes. Ties are always on sale if you are willing to be a little flexible.
42. Always buy trim, tailored or athletic cut dress shirts. The regular size is made to fit the fattest people that have the same neck size and sleeve length as you. I am not skinny but regular shirts even make me look like I am wearing a tent. I buy trim shirts.
43. I am not giving you these rules to try to make you become a business executive, lawyer, doctor, architect, teacher, engineer or accountant. You can be whatever you want. If you do become a construction worker, you will have a different wardrobe with less in the way of suits and sport coats but you still will occasionally need to dress up.
44. Also, just because I point out that something is considered dressier or more formal, that doesn’t mean that I go for that look all the time. Often, I go more “casual” in a business setting because I don’t want to be too intimidating. For instance, today I wore a patterned shirt, cords, a tweed coat, no tie and casual shoes. I still looked like a lawyer but a more approachable one. If I was going to be in court or meeting with another lawyer from the cities, I would have worn a suit. I try to dress one or two steps above my expected daily audience. Again, I would like the people with whom I come into contact to simply not remember what I was wearing – just that I seemed professional, knowledgeable and appropriately dressed.
All of this won’t mean much to you right now. Go ahead and wear your hoodie, jeans and tennis shoes tomorrow. I just wanted to give you these tips for down the road. You will recognize when you will need them.