".....After finding a reference of Rivka doing it when meeting Isaac, and the removal of the head covering by the priest from the woman presumed to be adulterous... I then found several other mentions of covering in the prophets that helped me to realize it was normative practice...
The wearing of head coverings is not a commandment but a principle that displays modesty to the public.
Rabbinic law has made it a commandment for both men and women to cover thier heads when out in the marketplace for a sign of humility, and modesty.
Chasidic Jewish women wear wigs to fulfil this commandment... other orthodox women only do it once married... Though the Halakah clearly says that all women above the age of 6 , I believe should do so...
Now to my current thoughts...
1) The Times... There was a time when... (and in some parts of the world still) The exposure to female shapeliness and skin was a rarity... So, definitive desplays of femininity like the hair would have been highly erotic to an un exposed public...
Today, when we can see the shape of a woman thanks to tight jeans... and 2 piece bathing suits, it takes a lot more to get a man worked up... Though men still prefer long flowing hair on a woman... and will smell it and pull on it during sex... It is not a cultural sign of modesty necessarily to have ones head covered... Though depending on the covering style... Others might easily identify a woman as "religious" and pious... not necessarily "modest"...
2) Freedom... While I agree that if you want to be part of a religious group that promotes head covering as a normative practice for those who are a part of the group... One should make the best efforts to represent that group according to it's standards...
I do not believe that a woman who covers her head is any more "spiritual" or holy than one who does not... Since it is not a Torah command... but rather assumed as normative in Torah for the times... and It is a Rabbinic command... One need only concern themselves with compliance if they were Jewish converts or native born. Even then it would be more for the "community" than for G-d.
My freedom point is this... everyone should be allowed to fully walk out thier convictions without fear of what other may think or believe... nor should we invest time in trying to get other to comply with religious rule we have placed on ourselves... no matter what the source...
3) Not Necessary... But It is Attractive... The truth is that men while they will persue the sexy woman for sex... the desire the modest woman for a wife... Men know that the ideal woman to spend your life with will not be the one putting it all out there for everyone else to see...
Men and women both get out of the mating dance of "peacocking" once they have settled with a mate... BUT... Men being the visual creatures that they are... will always be attracted by the woman "putting on the show"...
I would tell your friend that unless looking to become orthodox or Menonite... I would not concern myself with covering my head unless It developed as a personal conviction for me...
Below are 2 quick videos I posted to YouTube last month about a very simple/frugal/casual headcovering: