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Originally Posted by F. Corbera 
1. Navigate all elements of each “fit” to one point in the path from country to city: thinking about the casual suit
Rare is the man who cannot look well turned out in a decent black tie rig. Rare, too, is the man who cannot look splendid in a discreet, unmarred city ensemble.
Why not dress in both every day, then? Awesome, right?
“Black tie every night?” you think, “That’s nuts.” It is.
Wearing a city look every day might be nuts for you, too, though.
I am hoping that you, as a beginner, have given this some thought at this point in this thread and have made a decision on which way to go.
If a city look does work for you, execute the basic and unimpeachable versions of it first until everything about it becomes second nature. The combinations are simple and known. What will happen if you are interested in clothes is that such simplicity will lead you to thinking productively about quality and fit. It will not be dour, it will be great fun.
If a city look does not work for you, rather than going first to the country/casual clothes department to accessorize and rusticate your charcoal gray pinstripe, what I would like you to consider instead is what we will call the casual suit. In the old days we might have called it a weekend suit or even a Friday suit. . . .

1. Navigate all elements of each “fit” to one point in the path from country to city: thinking about the casual suit
Rare is the man who cannot look well turned out in a decent black tie rig. Rare, too, is the man who cannot look splendid in a discreet, unmarred city ensemble.
Why not dress in both every day, then? Awesome, right?
“Black tie every night?” you think, “That’s nuts.” It is.
Wearing a city look every day might be nuts for you, too, though.
I am hoping that you, as a beginner, have given this some thought at this point in this thread and have made a decision on which way to go.
If a city look does work for you, execute the basic and unimpeachable versions of it first until everything about it becomes second nature. The combinations are simple and known. What will happen if you are interested in clothes is that such simplicity will lead you to thinking productively about quality and fit. It will not be dour, it will be great fun.
If a city look does not work for you, rather than going first to the country/casual clothes department to accessorize and rusticate your charcoal gray pinstripe, what I would like you to consider instead is what we will call the casual suit. In the old days we might have called it a weekend suit or even a Friday suit. . . .
My original post was to describe a choice I had to make that I thought was relevant to the topic. Then I thought "who cares" and deleted it. But since my choice was to wear a "weekend" suit of the type Vox described just above, I will mention it again -
I was invited to a dinner party in someone's home into which I knew a lot of effort had been put (both the home and the dinner). The home is very over-the-top-but-still-formally decorated. I also knew that while the hosts were not strictly conservative or formal dressers, they were not necessarily casual about dress either (at one of their prior parties, I recall that one of them wore a corset). A tweed jacket didn't seem right but neither did a serious business suit. So I went with Despos's favorite spongy black & white houndstooth suit, light blue shirt and a black grenadine tie.


















