20 Gentleman’s Rules of Dress

William Wilson, CEO

When men look at me and tell me, “I don’t own a suit.”, my first thoughts are, “Where do you take you lady when she wants to be treated like Cinderella? Where do you take her to celebrate those monumental occasions? What do you wear when you are trying to make a good impression somewhere?” You can tell a lot about a man from his closet. Ladies, look in his closet, and you can see where you will spend most of your life with this man. If everything in his closet can be worn as appropriate dress to a bar or club, don’t expect to spend much time at the most exclusive places in town. If it’s full of blue jeans, t shirts, and 2 pair of slacks, don’t expect to see a pair of Jimmy Choo’s in the near future. And if you do, be prepared to be going out with your girlfriends when you wear them.

But for those more refined in our dress, and want to look our best for ourselves and the important women in our lives. I present to you “The 20 Gentleman’s Rules of Dress”. Yes, contrary to the thoughts, and dress of my sartorially challenged brethren, there are rules to fine dress. These rules have been passed down from generations of fine dressers. Men who take pride in not only looking like a gentleman, but being a gentleman. Men that understand that true power makes it impossible to go unnoticed. Gentlemen that understand that your wardrobe speaks when your mouth is closed. For these gentlemen, the rules of dress are not just a guideline, but a way of life that is time honored, and respected to the furthest degree. Remember, there is a reason that when you see photographs of the most successful men in the world, 95% of the time, they are wearing a suit. Jeans are for dress down, not for everyday. I will not give all the rules today, but I will give you enough to get started.

Rule #1: Proper fit is everything. Nothing cheapens your look like ill fitting clothing, especially a suit. If you can afford it, buy custom. There is no substitute for clothing made specifically for your body, and per your individuality and likes. But if custom isn’t in your budget, buy off the rack, and have it tailored at your alterations shop. We call that “Poor Man’s Custom”. Trust me, it’s far superior than strictly wearing it straight off the rack.

Rule #2: A gentleman’s closet should have a minimum of 4 suits. 1 black, 1 gray, 1 navy, and 1 brown or tan.

Rule#3: Don’t brag about an off the rack suit. A gentleman knows the most important name in his suit is his own. Therefore, he buys custom. If you spend over $1000 on a suit, and you buy it in a store, you are being taken as a fool. Store suits, even Gucci, Prada, Armani, and Brioni are mass produced suits that cost the department store less that $200 to buy. They depend on the brand name being sufficient to make you ok with overspending on their product. A real luxury consumer has his suits and shirts made. As I said in a Facebook status once, “Big dogs have tailors, not store receipts.”

Rule #4: Suits should be 100% wool, or linen suits. There is no exception

Rule #5: Your suit for church may not be appropriate for work. If you wear a gray suit, gray hat and gray gators; that may fly in church- not in corporate America.

Rule #6: Do not button the bottom button of your suit or vest. EVER!!

Rule #7: Your jacket sleeve should never touch the back of your hand. If it does, the sleeve is too long. Period. End of debate.

Rule#8: A little of your shirt sleeve should show below you jacket sleeve.

Rule #9: Never wear a button down collar with a tie. A button down collared shirt is a sport shirt, not a dress shirts. It’s tacky, and in poor taste. And before you say, “I see men wear that all the time.” I see kids with their pants hanging off their butts, but that doesn’t make it proper dress. It’s the equivalent to wearing flip flops with a suit.

Rule #10: There is no such thing as a short sleeve dress shirt. Unless you work for Geek Squad,  NEVER wear a short sleeve shirt with a tie.

Rule #11: Always wear a t-shirt: T- shirts not only make a white shirt brighter. It also serves as a barrier to the skin so your shirt doesn’t stick to your skin (which looks horrible, by the way). It also absorbs mild perspiration and allows the shirt to not only hang better, but provides longer wear.

Rule #12: Dress socks should always cover the calves. I hope I don’t need to explain this. Also, socks should match, or be darker than, the suit.

Rule #13: Ties should be made of silk. Do not wear polyester ties. And for goodness sakes, do not wear a tie with fish, or cartoons, or that craziness. The only exception is on Father’s Day, and only if your kid bought it. If your wife bought it, tell her you love her, then proceed to explain why you CAN NOT ever wear that tie in public.

Rule #14: The Windsor is the gentleman’s knot. It’s symmetrical and looks good with every collar. The four- in- one knot (which is most common) is a juvenile knot. the 4-in-1 is the one that always looks like it is crooked, no matter what you do. That’s because it’s an uneven knot pattern.

Rule #15: Cufflinks are never inappropriate. Cufflinks make a statement. They say power, style, and sophistication. If these aren’t you, well…..

Rule #16: Always wear a nice watch. It doesn’t always have to be expensive. But buy the best watch you can afford.

Rule #17: Never need a haircut. It shows poor hygiene to look unkempt. Specify a day to get your haircut every week, and put it on your calendar.

Rule #18: Maintain detail hygiene. Your nails should be trimmed, beard and mustache maintained, and your shoes should be shined. Trust me, ladies notice.

Rule #19: Don’t swim in your cologne. Your cologne should be a pleasant accent to your image, not show up 10 paces before you and then just linger after you leave.

Rule #20: Increase your vocabulary. You ask what does this have to do with dress? There is nothing more disappointing than a man that looks like he came off the cover of GQ, then when you speak to him, he sounds like he failed the 9th grade- last year! Your vocabulary is a vital part of you appearance.

These are just a few of the rules to dress. I understand that not everyone is financially able to buy custom suits. That’s ok. If you can’t afford it, then buy off the rack and have an alterations person take the suit apart and fit it to you better. It won’t be as good as a custom suit, but it will look much better. But the other rules are easily adaptable, and a must if you want to look like a true, well dressed gentleman. Fine dress is not a game, it’s a lifestyle and it is important to realize that you are addressed by the way you dress. Your outward appearance is a direct reflection of what you feel inside. And it’s what people respond to. As my friend, Bill Wiley, once said. ” If you don’t get your props it’s probably your wardrobe’s fault!!! Until next time…

God bless and dress well,

William Wilson, CEO

William Wilson Clothing


One thought on “20 Gentleman’s Rules of Dress

  1. Thank you for the wonderful job you are giving to guys. my comment is a bit controversial which is about men wearing ear ring.the origin of wearing ear ring by men particularly African_Americans is of slavery origin according to what i read on net.i want you to talk more about that,is it a modern thing or guys do it in the name of faction

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