Earlier quoted context omitted.
> He also bought a new wardrobe and replaced his old worn out logo T-shirts and cargo shorts with clothes more appropriate for an adult. I think the problem many __men__ have with that is that an "appropriate" wardrobe looks more uniform and less individualized, basically boring.
The key point in his change was that he started looking like someone who cared enough to put some minimal effort into dressing himself. It’s not about being uniform or bland. He went from old worn-out clothes he didn’t care about to wearing clothes that were appropriate for a business casual environment or a casual date. When you start dressing like you care, regardless of how unique and individualized, others notice…
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.