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Jenn, you look amazing in all of these -- but the cashmere sweater dress is just incredible on you! Wow!!
"Well past 30 wears" is a real achievement when you have a smaller wardrobe and perhaps especially in a warmer climate where you will be wearing even more of your items year round.
Back to add that an assortment of black dresses makes total sense to me. I have an assortment of navy (my dark neutral).
The dressy sheath in my own closet is not t his colour but a bright navy. I also have another navy dress, not pictured -- a sleeveless knit not in my Finds because it is so old (predates Finds and I never took a photo yet).