The Prescriptivists: On Rules and Rule-Breaking in Men's Dress

Style and flair within the confines of accepted taste -- neither hidebound to rules nor straining for iconoclasm -- are what characterizes great dressers.
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It's 23 days into the autumnal equinox here at 40.77 degrees longitude and 73.9 degrees latitude. The relative humidity is 66 percent, and the temperature, sometime between one and three p.m,, will climb to a high of 69 degrees.

I know precisely what to wear.

It's all thanks to the website A Suitable Wardrobe, which includes a detailed weather report in most of its posts. In the six years since its founding, the weather has been the single most recurring motif in its editor's expositions on the niceties of style. Given that the weather is considered a topic on which only those with nothing else to say ever deign to converse, it's certainly an odd way of approaching the topic of style. The date on the calendar and mercury reading are certainly indisputable facts, and so, the logic goes, the "gentlemanly" choice of attire consists of somesuch fabric in somesuch weight.

This approach to dressing is diametrically opposed, as summer is to winter and day is to night, to that rare ability to "pull something off."

"Pulling something off" -- say, a chesterfield coat over an oxford shirt and gray sweatshirt, paired with jeans and bit loafers and accessorized with a baseball cap and toasted bagel -- is something that really gets the prescriptivists' boxers in a bunch, for pulling something off requires breaking rules.

The prescriptivists, of course, are those menswear personae who get inordinately obsessed with rules of appropriateness. Style Forum uber-member Michael Anton seems to fit this category. In 2006 he brought out The Suit under the pseudonym Nicholas Antongiavanni; it's full of pronouncements such as "I will judge him to be well-dressed," who has successfully done this or that. Granted, it's supposed to mock the language of Machiavelli's The Prince, but the spirit behind it seems genuine. Anton is a pleasant fellow, but when you meet him you feel a cold scrutiny pass over you like an open window in February.

It takes a certain kind of personality to approach style from the sharp right angle of correctness, but each year new prescriptivists arise with websites such as Rules For My Unborn Son and books that tell you a gentleman does this or that -- it's a genre as old as the middle class itself.

Justin Jeffers is one of the latest to enter the fray. An enthusiastic twenty-something who blogs under the name The Fine Young Gentleman, Jeffers has compiled a list of rules phrased in "thou shalt" language suggesting they were dictated by a Supreme Being. A few examples:

• Thou can wear black shoes with a navy suit/pants.
• Thou shall wear a belt when wearing pants with belt loops.
• Thou shall not wear a French cuff (double cuff) shirt without a jacket.
• Thou shall not wear slip on shoes with a suit. In fact, they should be avoided.

I asked Jeffers via email what motivated him to create the list. "The Rules Of Men's Dress was formed out of a love/hate relationship I have with rules," he responded.

I felt that there were many fundamental things that were being neglected, and if said things were addressed by the average male the level of his personal appearance would significantly increase. But the problem I ran into when reading other blogs and writings on mens style and dress was that there was no centralized list of rules or fundamental pointers.

("Centralized list," of course, is euphemism for The Ten Commandments, though in this case there are 45.)

Of the public's response, Jeffers says:

Some have told me they love the list, both for its content and its blunt and snarky tone. For they too were in need of a list of basic guidelines to follow. Others have criticized it, mostly saying my rules are dumb or antiquated. Others have said rules are meant to be broken. To this point I agree; to an extent. Some rules are okay to break, however, it must be done tastefully.

I read a few of Jeffers' rules to Alan Flusser, the modern godfather of rule-based dressing. He appreciated the impetus behind it and offered the young man encouragement. "He's erring on the side you'd want to err on. If you were to match all your metals and wear socks and pants of the same color, you'd be dressed better, not more poorly."

Though Flusser claims he has always dressed more eclectically than his books and tailoring shop would suggest, he also admits he's mellowed considerably with age.

As people who are style-conscious become older, they become less schematic. They become less serious and less driven to conform to some kind of arbitrary model. But compared to what GQ or Esquire say are the "rules" of dress for the season, I cut the guy who's young and dogmatic a lot of slack because I want to encourage him.

Though it sounds like a cliché, the notion that you need to know the rules before you can break them rings true. "Without rules there's very little to create of value," says Flusser. "The rules are there to learn and apply, but then you take them, like a jazz player, and do your own riff to reflect your own personality."

It's in light of all this that George Brummell's achievements are all the more remarkable. Brummell was the right man in the right time and place to set rules, not follow them. He had the style and courage to wear what he pleased, others be damned, though it didn't take them long to realize the superiority of his costume.

I think it's equally as foolish to slavishly follow rules as it is to attempt to dress "original." Your clothes aren't supposed to be original (though they may be custom-made), you are. It is in limitations that the master reveals himself, according to Goethe. Style and flair within the confines of accepted taste -- neither hidebound to rules nor straining for iconoclasm -- are what characterizes great dressers.

On that note, an emerging ray of sunshine signals it's time to disengage myself from the keyboard and put on that outfit. It's less likely to be a Platonic ideal of gentlemanly dress for this day of the year and this particular temperature than an expression individual caprice, but I'm sure I'll be comfortable.

And for the record, there's no way in hell this outfit will include a buttondown collar paired with a double-breasted jacket. That would just be wrong.

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