Perfecting the closet and the influence of catholic school uniforms

I have a love/hate relationship with my closet, and my powers of purchasing.  I am acquisitive (albeit on a budget) and love the search and purchase of the new, but I am also a bit of a minimalist - I don't like clutter, and at the end of the day (ok, the beginning of the day) I find myself wearing the same things - what I crave is the perfect, well constructed, beautifully tailored work "uniform" 10-15 pieces I can mix & mingle, snazzed up w/fabulous accessories (bags, jewelry, shoes).  The perfect black shift dress, camel above the knee skirt, black sweater, black ankle trousers, button down shirts (white, striped, silk, cotton), jean jacket, Chanel jacket.  What am I missing?  And if I find these perfect items, will I truly be satisfied?  Do I buy in duplicate (yes, you fool)? Can I really retire all of those fabulous, unworn/barely worn pieces that no longer fit my life OR style? 

I recently visited the mecca of "premium outlets" Woodbury Commons in #CentralValley, New York, and revisited some of my old haunts - I still love me the Prada and Gucci outlets, decided Jimmy Choo looks pretty cheap in an outlet setting (sigh), and can't understand why anyone would wait in a line ala DisneyWorld to procure Tory Burch. But then I'm a total label snob. (It all goes back to my childhood, when all my friends were wearing Lacoste alligators retail, and my sister and I had to wait to get ours at the summer sidewalk sales.  It SCARS you). 

I'll just keep hitting the Barneys sale (for as long as they are around), putting up with the attitudinal folks on the floor, ("No, we don't have that in another size - it's on SALE" - you know in their heads they are muttering "you peasant" - evidently I'm also a bit of a masochist), and believing, always believing, that perfection IS attainable.