The 45 Essential Rules of Men’s Dress December 31 2014

As many of you know, style is relative, which leads to a situation where there is no single list of men’s dress rules that are all-encompassing and without exception. However, the following is a list of dress rules that Avallone stands by. Some of these rules are without exception, such as not wearing a crew neck undershirt when the top button of the shirt is left unbuttoned. Other rules have exceptions, like the rule that a man’s socks should match the color of his pants. The rules presented here are taken from many different sources including tradition, classic men’s dress rules, and personal taste.

  1. Match the metal of the bit on your loafers, belt buckle, suspenders, blazer buttons and cufflinks.
  2. You do not need to match the metal on your watch with the other metals you are wearing, however, it is preferable.
  3. You can wear black shoes with a navy suit/pants.
  4. One must only wear black, brown or oxblood (burgundy) leather shoes for business dress.  The only exceptions allowed are white bucks.  Blue, green or any other colored shoes are inappropriate.
  5. One shall match the color of his socks with the color of his pants.  As an exception, socks can be matched to something worn above the waist such as a man’s shirt, tie, pocket square or suspenders.
  6. One must match the color of his belt to that of his shoes.  This holds true in all situations except when wearing white bucks.
  7. You do not need to match the leather on your watchband with that of your shoes and belt, however, it is preferable.
  8. Wear a belt when wearing pants with belt loops.
  9. Never, ever, ever use your belt to hold accessories like beepers, phones, Blackberrys, ID tags and/or keys.
  10. If pants do not have belt loops they should have side tabs and/or  buttons for use with suspenders.
  11. You shall never wear a tie and pocket square of the same pattern.  The talking heads that do this on television look like fools.
  12. One must not wear a French cuff (double cuff) shirt without a jacket.
  13. You must always doubt salespeople and in-store tailors opinions on fashion, style and fit. The stores they work for pay them, not you.  Their motives are to sell products to who will buy them, not necessarily to who will look best in them.
  14. You must not wear slip on shoes with a suit.  In fact, they should be avoided.
  15. Never wear flat toe/square toe shoes.  They should be avoided like the plague.  They are cancerous to a man’s wardrobe.  They are aesthetically offensive.  Their sole purpose lies in showing men what not to wear. 
  16. Patent leather shoes are only for black tie (semi-formal) and white-tie (formal) occasions.  Patent leather is never acceptable to be worn in a dress or causal setting.
  17. Never wear a long necktie for a semi-formal (black tie) affair, even if that tie is solid black.
  18. You can wear brown suede shoes for business dress.  They are elegant and gentlemanly.
  19. Do not wear Chesterfield coats, which are typically signified by a velvet collar, with anything of less formality than a suit.  They should not be worn with business casual attire.
  20. Do not wear a tie without a jacket.  If done so, you will run the risk of looking like a waiter at TGI Fridays.
  21. Do not wear suspenders without a jacket. 
  22. Only wear suspenders that utilize buttons, not clips. 
  23. Do not wear a crew neck undershirt when the top button of a shirt is left unbuttoned.  When leaving the top button unbuttoned you must wear a v-neck undershirt.
  24. One can wear brown suits for business dress.
  25. Only wear shirts with white collars and white cuffs with a jacket.  These shirts should not be part of a business casual wardrobe, that is, one where suits are not utilized.
  26. Leave the bottom button of vest (waistcoat) unbuttoned.  Except when wearing a double breasted or flat bottomed vest, in which case the bottom button should remain buttoned.
  27. Iron the collar of a shirt before wearing it.  Creased collars caused by dry cleaning and hanging do not follow the natural circularity of one’s neck.
  28. Utilize a pocket square when wearing a jacket.
  29. Pocket squares are underrated, underutilized and most importantly they are awesome.
  30. Do not wear a shirt with any type of logo on it in a business setting, including when in business casual dress.  These shirts should be reserved for casual wear.
  31. Wear your tie bar at a slant, not horizontal.
  32. Off color shirts with a white collar should have French (double) cuffs, regardless of whether or not the cuffs are white or the same color or pattern as the shirt.
  33. Life is more fun in a tuxedo (dinner jacket).
  34. Never button all three buttons of a three button jacket. Sometimes the top, always the middle and never ever ever the bottom.
  35. Wear over the calf socks as opposed to crew socks whenever possible.  They are far superior in both form and function.
  36. Do not wear a solid black suit for business or professional activities.  Save it for formal events and funerals.
  37. Style is a state of mind.
  38. It is impossible for a man to be considered well-dressed if his shoes are in poor taste or of noticeably poor quality.  Any good ensemble is built on a fine pair of shoes.
  39. Do not wear sport sunglasses with a suit.  It’s like wearing socks with sandals; everyone else knows its wrong, why don’t you?
  40. Do not wear a sports watch with a suit.  It would be like playing lacrosse in dress shoes, and no one wants to see that.
  41. There should be no presence of logo or branding when wearing a suit.  For example, do not wear a Polo shirt with the Polo logo on it under a suit jacket or a Burberry tie with the Burberry tartan (although the scarfs are fine).  The emphasis of a suit should be the fit, not the brands it is worn with.
  42. It is better to be overdressed than underdressed. A man does not need an excuse to wear a tie or jacket.  In other words, a man does not need an excuse to dress up.  Despite the fact that in today’s society it seems he does need one.
  43. Never, ever, ever wear a black dress shirt with a suit (or a dinner jacket/tuxedo for that matter).  Just because they may be or may have been ‘on trend’ does not mean one will ever look good on you.
  44. Take off your sunglasses when talking to someone else who is not wearing sunglasses, unless you are at the beach or pool.
  45. Take off your sunglasses when inside.