Seriously.

I really like it when people LIKE what they wear. So do that, and you really can’t go wrong. When I purge, the only question I ask myself is, “How do I feel when I wear this?”

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My basic list (and I work in a fairly creative profession, but I think there’s more latitude in these things across the board than there used to be)is:
1) a cocktail dress you love (people don’t wear formal-length gowns much anymore — if you need one randomly, you can buy it, or borrow one, but having one in your closet just takes up space)
2) really flattering black pants
3) a neutral cardigan (black/blue/brown, even red can be surprisingly neutral. All the white on this list gives me hives)
4) a cashmere v-neck in a flattering color, a white button down, a black turtleneck (or vice versa) and tees or tanks in a variety of colors
5) a pair of really flattering darker wash jeans
6) a really, really good quality bag (you use it every day; a good bag elevates every outfit), as well as good quality shoes (heels, flats, casual kicks, boots)
7) A light peacoat or trench a casual blazer or jacket
9) a wrap dress you can wear to work or dress down on the weekends
10) If you work in a job that requires it, a beautifully made classic black, grey or navy suit. I think you really only need the blazer, pants and a slim-fitting knee-length skirt. I honestly don’t know where you could find a chic ankle-length skirt suit, and I hate to dwell on that, but it troubles me that people might actually be wearing those.

I am kind of a clotheshorse and I work in fashion, but I really believe that you will get more wear out of well-chosen, high quality pieces that you LOVE than khakis you buy because they seem practical.