That is a very interesting theory and all, but have you bothered to think it through? Barack Obama is the most powerful man on the planet at the moment and he wears dad jeans. Running the world and devotion to fashion don't have much in common.
If I could pick three people to invite over to dinner between Jesus Christ, Justin Bieber, Kim Kardashian, Mahatma Ghandi, Vanilla Ice and Mother Teresa, I would go for the three who spent the least amount of money on their wardrobe.
Are you talking about the same Barack Obama that wears a tan suit?
The correct answer is to spend more time with fashionable people.
Being unfashionable is nothing to be proud of. Socially outcast nerds do not know this. They revel in their own unattractiveness, while the rest of society disparages them.
Do not be proud of being ordinary.