JudyDenmark said: "Maybe it’s just because I’ve never really cared aboutthe fashion world, but it always makes me scratch my head that the people who “don’t care what anyone thinks” are the one who dress outlandishly. Isn’t the entire point of that because you care what people think? I mean, maybe you don’t care about expectation, or about feeling the need to fit in a box, but dressing likethat is precisely to attract attention as an eccentric and show people that you don’t care about their box. If you really didn’t care what people think,you’d wear, like,t-shirts and sweatpants."
But if he enjoys fashion and dressing in different ways to express himself, and that makes him feel good, then maybe that's his version of what would be t-shirts and sweatpants to you. The "I don't care what people think" is more referring to, "I don't care if people expect a big shot theatre producer to wear Prada suits. That's not how I want to express myself, those suits don't currently reflect me."
For some people, what they wear can really boost how they feel. I'm more comfortable sitting around in t-shirts most of the time but when I put on a fancy dress it can sometimes make me feel like I'm ready to take on the world.