For a culturally stimulating watch that familiarizes you with one of the icons of the men's men's men's world that fashion was and still is to a large extent, get Diana Vreeland: The Eye Has to Travel (2011).
Introducing Diana Vreeland (1903-1989) - especially to those that were born after her epoch in Vogue had already ended - and through archive footage and people that knew her showing that:
You don't have to be conventionally pretty to have fun with dressing-up and to become a style paradigm on your own.
You don't necessarily need a formal education to be good at something and get a job that you are passionate about (although this part is clearly much harder than it was in the 1930's).
You may realize and act upon the fact that family life may just not be for you. Nevertheless - and as the children of Diana confirm - would be nice to realize that before actually bringing any children into the world.
You should be able to express yourself and speak clearly and loudly from your most authentic self. This is not a victimless advice, of course, but the clear satisfaction you can see in Diana's face when commenting on how she perceived the world is priceless. (Again, this is not to promise that just anybody can become the editor-in-chief of Vogue, but to encourage to practice creative self-expression whenever and however you feel it to be adequate. And maybe a bit over the top too.)
You should - to the extent that's possible, obviously - surround yourself by things and people that entertain, educate, and inspire. Because the eye (and the mind) has to travel.