And Now For Something Completely Different (Again)

My good friend Rebecca was in town, and I elected to put off everything I had to do then until today, which I am putting off even further to write this blog post. This is how you live responsibly in the 21st century, folks. I thought of this post from “The Fine Young Gentleman”, which is not a blog I frequent, but one that Rebecca sent me once when we were talking about style. I thought I would take another gander at this rather exhaustive (49 points!) list and give my own thoughts on each one. As a caveat, all of this is generally good advice in my opinion, but sometimes sticking to close to conventions lands you in more trouble than it will get you out of. Without further ado:

RULES OF MEN’S DRESS (annotated)

1.      Thou shall match the metal of the bit on his loafers, belt buckle, suspenders, blazer buttons and cufflinks.

Generally preferable, but not really that big a deal. It will have more of an affect on how you feel wearing the outfit than on how anybody looks at it.

2.      Thou need not match the metal on his watch with the other metals he is wearing, however, it is preferable.


3.      Thou can wear black shoes with a navy suit/pants.

Agreed. This tends to look more business-like, though.

4.      Thou shall 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.     White bucks are badass.


6.     Thou 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 (braces in the UK).

Good general rule of thumb, but there’s nothing wrong with accent socks.

7.     Thou shall match the color of his belt to that of his shoes.  This holds true in all situations except when wearing white bucks.

This does not necessarily hold true when wearing casual shoes, such as sneakers. 

8.     Thou need not match the leather on his watchband with that of his shoes and belt, however, it is preferable.


9.     Thou shall wear a belt when wearing pants with belt loops.

100%, non-debatable, true.

10.  Thou shall never, ever, ever use their belt to hold accessories like beepers, phones, Blackberrys, ID tags and/or keys.

Only OK if you’re working in a non-office setting.

11.  If pants do not have belt loops they should have side tabs and/or  buttons for use with suspenders (braces).

I guess? I’ve never seen any belts that don’t have either belt loops or side tabs, but I don’t think I would dismiss them out of hand.

12.  Thou shall never wear a tie and pocket square of the same pattern.  The sports commentators who do so look like fools.

Yes. This is the mistake that everybody makes their senior Prom.

13.  Thou shall not wear a French cuff (double cuff) shirt without a jacket.

Who would ever do this?

14.  Thou shall 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.

Generally true, but there are exceptions. I’ve found this especially holds true as a younger guy when dealing with older sales people (they always want me to wear a size too big).

15.  Thou shall not wear slip on shoes with a suit.  In fact, they should be avoided.

Judging by #16, I guess we’re to assume that slip-ons are different from loafers. Slip-on sneakers (and any sneakers) should not be paired with a suit. Saying you should avoid slip-on shoes altogether is stupid.

16.  Thou can wear loafers with a suit, however, this is mostly practiced in America.


17.  Loafers are badass, especially those with bits or tassels.


18.  Thou shall not 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.  Money spent on these would have been better spent on Enron stock circa June 2000.

Yes. The lone exception would be certain styles of cowboy boot.

19.  Thou shall only wear patent leather shoes for black tie (semi-formal) and white-tie (formal) occasions.  Patent leather is never acceptable to be worn in a dress or causal setting.


20.  Thou shall never wear a long necktie for a semi-formal (black tie) affair, even if that tie is solid black.

This seems a little dated, but I would probably agree that you should err on the side of caution.

21.  Thou can wear brown suede shoes for business dress.  They are elegant and gentlemanly.


22.  Brown suede shoes are badass.

Brown suede in general is badass.

23.  Thou shall 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.


24.  Thou shall not wear a tie without a jacket.  If done so, he will run the risk of looking like a waiter at TGI Fridays.

Generally true except for the most stylish of dudes.

25.  Thou shall not wear suspenders (braces) without a jacket.  Sorry hipsters.

Generally true, but you could make it work. 

26.  Thou shall only wear suspenders (braces) that utilize buttons, not clips.  Again, sorry hipsters.

Don’t care.

27.  Thou shall not wear a crew neck undershirt when the top button of a shirt is left unbuttoned.  When leaving the top button unbuttoned thou shall wear a v-neck undershirt as The Dude does.  The Dude abides.

I actually think an exposed crew neck undershirt with a very casual thing like a plaid flannel can look good. Don’t do this with sport shirts.

28.  Thou can wear brown suits for business dress.

Yes, but it will probably make you look British.

29.  Thou shall 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.

This is weird. I’m going to assume they mean contrast dress shirts (ie: shirts with white collars and cuffs that are a different clor throughout the rest of the shirt), since saying you can’t wear a white shirt in a casual outfit is dumb (you should roll the sleeves up though, and that collar should be loose and open)

30.  Thou shall 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.

I think we should all agree to amend this to “vests usually look terrible”.

31.  Thou should 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.

Ain’t no one got time fo’ that.

32.  Thou shall utilize a pocket square when wearing a jacket.

Feel free, but this not a hard and fast rule. If you want to be more simple and thus more elegant go without.

33.  Pocket squares are underrated, underutilized and most importantly they are badass.

Slippery slope with this one.

34.  Thou shall not wear a back pack/book bag when in business dress, especially when in a suit.  Book bags are reserved for casual wear and students.


35.  Thou shall 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.


36.  Thou shall wear a tie bar at a slant, not horizontal.


37.  Off color shirts with a white collar should have French (double) cuffs, regardless of whether of not the cuffs are white or the same color or pattern as the shirt.


38.  Life is more fun in a tuxedo (dinner jacket).

Generally true.

39. Thou shall never button all three buttons of a three button jacket. Sometimes the top, always the middle and never ever ever the bottom.

Gospel truth.

40.  Thou shall wear over the calf socks as opposed to crew socks whenever possible.  For they are far superior in both form and function.

Depends on how long your pants are.

41.  Thou shall not wear a solid black suit for business or professional activities.  Save it for formal events and funerals.


42.  Style is a state of mind.

Or lack thereof.

43.  It is impossible for a man to be considered well dressed if his shoes are in poor taste or of noticeably poor quality.  For any good ensemble is built on a fine pair of shoes.

Sounds like high society bullshit but is usually true.

44.  Thou shall not wear sport sunglasses with a suit.  It’s like wearing socks with sandals; everyone else knows its wrong, why don’t you?

Just don’t wear sport sunglasses ever.

45.  Thou shall not wear a sports watch with a suit.  It would be like playing lacrosse in dress shoes, and no one wants to see that.


46.  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.

In general, brand whoring is distasteful.

47.  It is better to be overdressed than underdressed.

No. It’s better to be dressed appropriately. A lot of people just tend to have a wrong idea about what this is. For example, being “dressed up” does not equate to tucking in your shirt (that has buttons!).

48.  A man need not an excuse to wear a tie or jacket.  In other words, a man need not an excuse to dress up.  Despite the fact that in today’s society it seems he does need one.

True, but in certain situations it’s going to make you look like a shithead, and looking like a shithead is never a good look. Don’t wear a dinner jacket to a dive bar.

49.  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.



One thought on “And Now For Something Completely Different (Again)

  1. Pingback: Black Dresses With White Collar | Tucson Pool Saz: Tech - Gaming - News

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