In certain industries, dress codes are not simply relaxed: it is actively frowned upon to suit up or dress well. The Tech industry in the old days was stylistically notorious for bearded hippies wearing jeans & t-shirts with funny/political/satyrical messages. They did not care about narrow elegance rules, but they had their very own flair and endearing style.

The above characteristic of the early days of tech was dissected, repackaged and taken to the extreme by the modern world. In tech, we now make an arms race (or a “rags race”) on how to dress down. We've even heard conversations of people boasting how little they spent on clothes. We've heard people making judgements on others solely on the fact that they’re wearing a nice pair of trousers. The whole problem reached its climax a few years ago, when a prominent Silicon Valley entrepreneur publicly declared “I never invest in someone who wears a suit”.

This mentality is based on the silly theory that clothes make you smarter or dumber. It is also based on the outrageous hypocrisy that dressing-down leads to a more egalitarian and meritocratic society.

In this episode we try to understand what is more elitist: a) a nicely-cut understated suit, or b) an Oxford or Harvard hoodie?

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