It goes a little deeper than "does not care" though: worn out can also be a symptom of caring a lot. Caring in the way of having a strong desire to identify with the stuff worn, and newly bought stuff just not checking that box. Then any newly procured garb, no matter how carefully selected, perhaps even customized, will feel like being dressed up as someone else. It's like a trap, just not being wired for new clothes. I wonder if there's a connection to childhood dress-up play, as in kids who had good times masquerading as some archetype are less likely later in life to fall into that "that's-not-me" trap regarding new clothes.

It's caring about the wrong thing if you're looking to improve your life though. You need to logically reason through norms and expectations and realize you gotta put on the correct costume for the setting, even if you don't identify with it.

Otherwise "Thats not me" will be describing things like "successful career" and "romantic relationships".

I wonder how clean the clothes looked, however. Clothes can be well worn but still appear clean and taken care of. There is a difference between "this is my favorite shirt" and "these are my grubbies I use while cleaning the house".

A man still strongly emotionally attached to faded, worn out logos from many years ago is probably not an appealing signal to most women looking for a man to date.