In my experience, you will lose in the dressing game if:
- You think that when you get dressed, it is unnecessary to combine your clothes properly.
- You are not satisfied with your existing clothes, but you also don’t want to change that.
- Fashion, style, and clothing are not your areas of interest.
- Your mother buys you most of your clothes. You are too lazy to do it for yourself.
- You underestimate the value of fashion and clothing.
- You never or rarely go shopping. You don’t know much about clothing stores in your area.
- You don’t invest your time, money, and energy in what you want to wear.
- You let other people decide what you wear. You should take their advice into account, but you should have your own opinion.
- You are not on the hunt for different ways to look better.
- You have other priorities in your life, and being well-dressed has not been in your list.
Although there are other factors which contribute to being not well-dressed, for example money, I only mention things you can change, and your attitude is closely related to them.