I know there are people out there who spend countless hours discussing the correct depth of trouser cuffs and length of coats. But the reality is that dressing well is like writing well: you learn the rules that are fashionable at the time, then you develop your own style by breaking them in order to better accommodate your unique life.

Those who slavishly follow the rules of dress are really just followers of fashion: the fashion of a particular time, past or present.

— Bruce Boyer (via Ivy Style)
Not Just Pedantry
The world of classic men’s clothing often feels like it’s filled with a dizzying number of arcane and archaic rules for how to get “properly” dressed. On one hand, I think people ought to not take these things too seriously. They are suggestions; not dictums. In fact, while I think these suggestions are useful, at the end of the day, you have to develop your own intuition for what looks good and dress according to your own eye. Not doing so can make you look a bit stiff; like you put on your clothes according to a “paint by numbers” diagram. 
On the other hand, these things aren’t just for pedantry. Knowing about the history of certain garments and how they’ve been classically worn can be quite useful. Take a simple issue, for example: knowing what details make a garment more or less formal. At one extreme of the formality scale is evening wear, such as the tuxedo, which is classically known as having a single button front, peak lapels, and jetted pockets. Less formal is the city suit, which can be a single- or double-breasted navy number with notch lapels and welted pockets. Less formal still would be a rustic sport coat, something like a checked tweed made with patch pockets, swelled edges, and possibly even elbow patches. The general principle here is that the more simple the piece, the more formal it’s considered, though each detail may have it’s own unique place in the canon (e.g. all things being equal, peak lapels are considered more formal than notch lapels simply because of their association with evening wear). It’s the sum of the details that make up the spirit and place of a garment. 
This may seem like a lot of unnecessary pedantry until you realize that these things could explain why a peak lapel, single breasted jacket might not look terribly right with a pair of country corduroys and Scotch-grain boots. Or why if you’re out shopping, you may want to avoid garments with contradictory details, as they’ll be harder to wear (e.g. an oxford cloth button down shirt made with French cuffs). Pairing shirts, ties, trousers, and jackets according to their formality, place (city vs. country), seasonal appeal (summer linen, winter tweed); and general aesthetic is what often leads to more successful ensembles. To do that, however, you need to know a little more about how a garment’s details defines it with respect to these dimensions.
Which is why knowing a bit about history can be useful. 

Not Just Pedantry

The world of classic men’s clothing often feels like it’s filled with a dizzying number of arcane and archaic rules for how to get “properly” dressed. On one hand, I think people ought to not take these things too seriously. They are suggestions; not dictums. In fact, while I think these suggestions are useful, at the end of the day, you have to develop your own intuition for what looks good and dress according to your own eye. Not doing so can make you look a bit stiff; like you put on your clothes according to a “paint by numbers” diagram. 

On the other hand, these things aren’t just for pedantry. Knowing about the history of certain garments and how they’ve been classically worn can be quite useful. Take a simple issue, for example: knowing what details make a garment more or less formal. At one extreme of the formality scale is evening wear, such as the tuxedo, which is classically known as having a single button front, peak lapels, and jetted pockets. Less formal is the city suit, which can be a single- or double-breasted navy number with notch lapels and welted pockets. Less formal still would be a rustic sport coat, something like a checked tweed made with patch pockets, swelled edges, and possibly even elbow patches. The general principle here is that the more simple the piece, the more formal it’s considered, though each detail may have it’s own unique place in the canon (e.g. all things being equal, peak lapels are considered more formal than notch lapels simply because of their association with evening wear). It’s the sum of the details that make up the spirit and place of a garment. 

This may seem like a lot of unnecessary pedantry until you realize that these things could explain why a peak lapel, single breasted jacket might not look terribly right with a pair of country corduroys and Scotch-grain boots. Or why if you’re out shopping, you may want to avoid garments with contradictory details, as they’ll be harder to wear (e.g. an oxford cloth button down shirt made with French cuffs). Pairing shirts, ties, trousers, and jackets according to their formality, place (city vs. country), seasonal appeal (summer linen, winter tweed); and general aesthetic is what often leads to more successful ensembles. To do that, however, you need to know a little more about how a garment’s details defines it with respect to these dimensions.

Which is why knowing a bit about history can be useful. 

Q and Answer: What Rules Do You Break?
Kevin writes: I enjoy your posts on PTO, especially those that have to do with the  rules and conventions of style, many of which I wasn’t aware or just  hadn’t considered.  I’d be curious to see a post at some point regarding  those conventions with which you don’t necessarily agree (or just don’t  care to follow).
Great question, Kevin!
I get the feeling from emails to PTO that some of our readers presume that the rules and conventions of men’s style are abitrary. They rarely are. Typically, they’re grounded in practical considerations, and serve as a shorthand for a complex web of reasoning.
There was a time when these rules were generally known, at least among the affluent (those with more than one or two sets of clothes). At the time, breaking those rules was a genuine act of rebellion. (Or a genuine act of ignorance.)
These days, few know the rules. Alec Baldwin plays a business executive obsessed with status on 30 Rock, but buttons the bottom button of his coat. Men wear flip-flops in nice restaurants. Steve Harvey exists.
For that reason, I think there is much more currency in knowing and following the rules than there is in breaking them. If I see a man walking down the street wearing loafers with his suit, I don’t assume he’s a rebel. I assume he’s a doofus.
If appearing to be a rebel is your goal, your mastery of the rules must be complete and consistent. In order for the point of difference to resonate, you must establish a perfect baseline of skill. It’s a bit like sprezzatura - if you’re Gianni Agnelli, and your watch is on your cuff, it’s sprezzatura. If you’re Jack Welch, you’re a slob or a weirdo. Few are the men I see who can break rules effectively, particularly in more formal dress.
That said, some rules are more relevant than others.
One rule that I break pretty regularly is the distinction between country and city clothing. This grew out of an aristocracy in England who kept country estates and city businesses - watch Jeeves & Wooster (set in the 30s) or the wonderful parlor drama Downton Abbey (set in the teens, and now airing in the US on PBS’ Masterpiece) for a glimpse of this. Country clothing was (at least outdoors) geared toward sport: tweeds, checks, twill trousers, brogues and boots. City clothing toward business: dark lounge suits or morning dress, black shoes.
I live in Los Angeles. Not only is it about as rural as a city can get - just the other day a giant coyote was doing stretches on my deck - it’s also a place where the distinction between country homes and city homes is pretty much irrelevant. I don’t even own one house, much less two. My career as a public radio and television host doesn’t require sober business dress. So: brown shoes and tweeds it is for me, at least in winter.
Also, I never wear pants after 2PM.

Q and Answer: What Rules Do You Break?

Kevin writes: I enjoy your posts on PTO, especially those that have to do with the rules and conventions of style, many of which I wasn’t aware or just hadn’t considered.  I’d be curious to see a post at some point regarding those conventions with which you don’t necessarily agree (or just don’t care to follow).

Great question, Kevin!

I get the feeling from emails to PTO that some of our readers presume that the rules and conventions of men’s style are abitrary. They rarely are. Typically, they’re grounded in practical considerations, and serve as a shorthand for a complex web of reasoning.

There was a time when these rules were generally known, at least among the affluent (those with more than one or two sets of clothes). At the time, breaking those rules was a genuine act of rebellion. (Or a genuine act of ignorance.)

These days, few know the rules. Alec Baldwin plays a business executive obsessed with status on 30 Rock, but buttons the bottom button of his coat. Men wear flip-flops in nice restaurants. Steve Harvey exists.

For that reason, I think there is much more currency in knowing and following the rules than there is in breaking them. If I see a man walking down the street wearing loafers with his suit, I don’t assume he’s a rebel. I assume he’s a doofus.

If appearing to be a rebel is your goal, your mastery of the rules must be complete and consistent. In order for the point of difference to resonate, you must establish a perfect baseline of skill. It’s a bit like sprezzatura - if you’re Gianni Agnelli, and your watch is on your cuff, it’s sprezzatura. If you’re Jack Welch, you’re a slob or a weirdo. Few are the men I see who can break rules effectively, particularly in more formal dress.

That said, some rules are more relevant than others.

One rule that I break pretty regularly is the distinction between country and city clothing. This grew out of an aristocracy in England who kept country estates and city businesses - watch Jeeves & Wooster (set in the 30s) or the wonderful parlor drama Downton Abbey (set in the teens, and now airing in the US on PBS’ Masterpiece) for a glimpse of this. Country clothing was (at least outdoors) geared toward sport: tweeds, checks, twill trousers, brogues and boots. City clothing toward business: dark lounge suits or morning dress, black shoes.

I live in Los Angeles. Not only is it about as rural as a city can get - just the other day a giant coyote was doing stretches on my deck - it’s also a place where the distinction between country homes and city homes is pretty much irrelevant. I don’t even own one house, much less two. My career as a public radio and television host doesn’t require sober business dress. So: brown shoes and tweeds it is for me, at least in winter.

Also, I never wear pants after 2PM.