If I were to evaluate philosophy by aesthetic criteria, I would say that a good philosophy should not be the equivalent of khaki pants, button downs, and loafers. Somewhere Deleuze says that a philosophy that causes no tears, no one to cry, is worthless. I don’t know that good philosophy need hurt, but I do think all good philosophy startles, surprises us, and fills us with a sense of wonder. It upsets doxa or common sense and commonplaces. It shouldn’t do this for the sake of being contrarian or counter-intuitive or shocking, but out of necessity: the necessity of the real or that which is unseen and unmarked in thought. A philosophy that simply confirms all that we think should be the case, our sense of how things ought to function, is a state philosophy and no real philosophy at all. If it carries no aura of the strange, the defamiliarizing, if it doesn’t unsettle and disquiet, it hasn’t fulfilled its function as philosophy. There’s a whole highly successful genre of philosophy that’s the equivalent of khaki pants. It’s celebrated because it confirms what we already thought and “makes sense”.