You might be short-changing yourself more than you realize. I was similar for most my life, but this year I decided to learn about fashion and actually dress nice. Not only do I look a million times better, but---surprisingly---it actually physically feels better when your clothes fit just right. It's like they're hugging you throughout your day as you wear them. Can't believe I went so many years without ever realizing this. Probably a lot here on HN who grew up poor and became "new money" through software dev are short-changing themselves like this.