From Alan Watt’s essay titled Clothes–On and Off in the book Does It Matter?:
Conventional male dress is trussing. It is tight, stiff, and constricting, and we are so habituated to it that many people feel vaguely guilty when, several hours after arising, they are still clad in some loose-fitting robe. The collar, the tie, the belt, the pants, the shoes, the tightly fitted jacket squeeze in on you with the information that you are indeed really and truly there. As if you didn’t know. Some people get it by lying on beds of nails, by walking to the Basilica of Guadalupe on their knees, by enduring Swedish massage, or by the curious sexual kick known as “bondage,” which involves being tied up with ropes in awkward positions and tickled with feathers. I am not contesting anyone’s freedom to use all these devices to enhance their sense of reality or “existential authenticity,” but I resent their authority over the rest of us–which compels me to go to fine restaurants, attend formal parties, and conduct business outside my home in grotesque garments which deprive me of ease and freedom and display little or no aesthetic imagination.
Deep down inside, we know life is a big act, and we each play our parts.
Wearing clothes is therefore a gesture which implies the unadmitted knowledge that our personalities are put on. Think of such phrases as “cover yourself,” “pull yourself together,” “tighten your belts,” “keep your hair on,” “don’t lose your shirt,” “caught with your pants down,” “shiftless,” “sound investment,” “redressment of injustice,” “defrocked,” “uncloaked,” “dismantled,” “name and address,” “wearing an expression,” “clothed and in one’s right mind,” “vested interest,” “stuffed shirt,” “good (or bad) habits,” “the bare facts,” and “the naked truth.” Such a list of sartorial symbols and millinery metaphors for mental and moral states, of depletions and completions of personality, might be expanded indefinitely. But they express a basic and intuitive recognition of the connection between who we are, as persons, and what we wear.
Why so serious?
Clothes, then, like our roles and personalities, should be worn easily and lightly in the realization that, because the whole universe is a masquerade, we may as well do it with the utmost flair and elegance.
If we can see the games we’re playing, might as well make the game a little more fun.
If you know you are a fraud from the beginning, you can afford to be exuberant and famboyant, and in any case, colorful and comfortable dress is a function of imagination rather than money.