My friends who are real wine experts don’t drink the best bottles at every meal. Of course they know good food is made better by drinking something special. But they also know that a rustic lunch goes perfectly well with something simple. Look around Sostanza and even the Italians are drinking the house red.
The same is true for dressing. Unless you’re a wild obsessive you don’t need the full bespoke every time you step out of the house. Hand-made clothes take time to make, require effort to maintain and are seriously expensive (though often justifiably so). When I was younger I tried to get the best thing I could afford (and sometimes couldn’t afford). That was a good education. But it also was a sign of a lack of confidence. I thought that there was something indicative about the quality based on the price of a dress shirt at Barneys or Bergdorf Goodman. Sometimes there is. Often there isn’t.
I’d rather not get into a deep discussion of why things cost what they do. But it’s safe to say that anything that advertises on television, has a store on Madison Avenue or pays an actor to be on a billboard costs too much. So let’s look for strategic sartorial tradeoffs that will leave you looking, and feeling, smart.