I truly appreciate everyone's input on this topic and all of your responses (way more than I anticipated). I had never given much thought to the perception of privilege (of which I am definitely not) and tried to do some internal searching on why this felt like the most comfortable representation of who I am. Here are a couple of my thoughts......
My cultural Environment growing up was anything BUT classic - Boho/Artistic/Hippy Chick - my mother was very anti-establishment even though she came from a fairly conservative background. Classic/Sporty was my way of rebelling against the status quo in our household (oh the twisted things teenage girls do to rebel!!)
My Interests and choice of Profession shaped my view of myself further and as a working Mom of 2 girls in a field that was predominately male, how I dressed and displayed confidence was in part reflected by my choice of fairly classic or sporty dress.
My Body Type is flattered by Classic choices easily - I'm a tall IT with some lingering athletic tendencies - Classic/Sporty and Natural Styles are comfortable and flattering on me.
But my Hippy Chick roots are still there and show themselves in the way I long for color - sometimes unusual color combos - the need for Baggy Khaki shorts with Birks..... remember I'm the one who never got rid of mine even when they were fashion suicide!! I think that is the basis of my total LOVE of the boyfriend jean - It's the best combo of Classic/Sporty/HIppy Chick I can find!!
I still own, wear and enjoy the standard classics - Ray Bans, Khaki shorts, Navy Blazers, WHite blazer, STRIPES of all iterations, pencil skirts and pumps, but I make them MINE in whatever sporty/hippy chick way I can.