It’s always fun flipping through the Japanese magazine Free & Easy and seeing all the botched English, such as “Made in trad.” Having spent a summer in Japan, I can assure you that nonsensical English used in advertising and the media provided hearty guffaws on the hour.

But sometimes the Japanese are unintentionally perspicacious, as in the top quote from the image above. The image is taken from the home page of Tokyo-based Tailor Caid. I’m afraid I don’t know much about the guy, save that he makes some beautiful jackets influenced by a variety of American cultural and historical references, and has a vast collection of vintage images that he posts on his blog. Every time my girlfriend goes home on a business trip I ask her to go see the guy, but she never seems to have the time. Perhaps our man in Tokyo can take on the assignment.

As for the top quote — “For the university young [and] the universally young” — it’s a clever and pithy way of describing a concept we explored in a recent post: namely, that the Ivy League Look is a unique genre in the history of American clothing, conferring dignity upon the young and youth upon the dignified. In the illustration above, we have a group of college men on the left and a gathering of finance or ad men on the right, who may or may not have looked like the men on the left when they were younger.

The second quote on the image — “We are not fashion snobs but we know a few simple rules” — is also astute, though I read it ironically.

First off, in a sartorial context let’s just replace “fashion” with “clothing” and so we don’t get too hung up on the F word. In fact, the Internet has introduced us to a particular breed of clotheshorse that we might normally only come across once in a lifetime: the snob whose snobbism derives from following rules of men’s dress that can either be quite sensible or ridiculously antiquated.

Now I have a veneration for tradition that runs across my personality like a rep stripe, but it’s spangled with crests of individuality. I may own a blazer, khakis, white buttondown, regimental tie, argyle socks and penny loafers, but I wouldn’t wear them all together and then feel smug about it. Of course that’s more of a formula than rules, though in the mind of the fusty clotheshorse the two certainly go hand-in-hand.

Bruce Boyer and I frequently chuckle over some of the more schoolmarmish personalities in the #menswear world. I asked Bruce for a fresh take on the whole concept of rules-based dressing, and here was his response:

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.

But the old saying holds true: fashion is for people who don’t know who they are. Guys who insist on rules of dress are either (1) stuck in some time period, (2) frighteningly insecure, or (3) don’t have any style of their own.

No one who has style is a slavish follower of rules, because style perforce implies individuality, character, and personality.

Well said, Bruce.

In the image above, the first quote feels like it honors the special quality of the Ivy League Look, that it has relatively fixed genre parameters that work well on young and old alike. But the second quote brings up the dark flipside of any genre-based approach to dressing, in which certain pedants will look not at the wide range of colors they have to paint with, and instead seek out numbers telling them how to do it.  — CHRISTIAN CHENSVOLD