Mom buys you clothes from the Sears catalog. Mom puts the clothes on you and says "you look so nice."
You are given a not-so-subtle clue that Mom wants you to be a"nice boy."
You start to take on the "nice guy" personal from an early age, not because it serves you well in all situations, but because you want to please the adults in your life.
As you get older, you're told to dress like a nice guy, look like a nice guy. Fit in, blend in, don't stand out. Don't offend anyone. Don't be assertive because it's too risky. Be cooperative. Be submissive.
This is our first experience in creating our personal style.
Eventually, most teenagers try some sort of fashion experiment, and most of the time his parents give him a hard time about it.
It's so common that it's become a cliche in our society.
As we get older, there are several different paths.
Some men get involved with a peer group that understands fashion. If you are around a lot of other guys who get it, you begin to feel like it's okay to take an interest. Or maybe you just copy what your friends are doing.
Then it feels very natural to develop a cool look.
Then there are the guys who are always looking for cool clothes, they really do take an active interest in fashion and grooming. They watch "Queer Eye" and read GQ. That's the minority.
The majority of guys never really change. They never leave behind their child-like view of clothing and fashion.
It's a challenge to reprogram your own fashion sense, just as it's a challenge to reprogram yourself to succeed with women.
It's a journey and it takes a lot of experimentation.