Okay. I missed this yesterday somehow.
First, you look sensational in every one of these! As others have said, no one would ever guess you're not a dress girl. Also, I respectfully disagree with T about the flats with the dresses she mentioned. With your slender legs you wear this look exceptionally well.
Now. Here is what I would do in your position. I would first take out any dress that doesn't fit right. (Okay -- you can keep if it can REALLY be easily be altered to fit. But first, think: If those alterations are so easy, and you love the dress so much, why haven't you done them yet? If you love it so much you want to wear it right now -- that's when you know you should buy (or keep) something. And if you want to wear it right now, you will fix it so it is wearable.
Assuming that you get rid of a few on that basis, then which ones give you super high happiness factor? Toss out any that do not.
With whatever is left, think about the TYPE of dress you need and will actually wear. Below are the types of dress that I can and do tend to use often enough to justify a place in my closet. Your needs will be different, but maybe it will give you some sense of how to decide.
Special occasion dress. I need at least one for summer and for winter. If I had more special occasions, I might need more. But this type of fancy event is rare in my life.
(1) My summer one is on the sexy side (cocktail dress) and can be used for date nights on the rare occasion we go somewhere dressy. (2) My winter one is sleeved and more sober and could go to a funeral or but it flatters me enough that it can also go to a winter wedding or similar. I probably wouldn't wear it to a cocktail type reception in winter or on a date night, but my dates and winter events tend to be super casual anyway (and I have some sparkly tops for the holiday season when they might be dressier).
Casual, MOTG dress. (3,4, 5) This is the kind of dress I can just throw on for errands, going to dentist or doctor, meeting my daughter's teacher, inviting friends over, going out for lunch with friends, or even an "at home" date with Mr. Suz, i.e. a night when we have supper on our own without the kid and watch a movie together.
The summer ones need to be cool, breezy, easy to wash. (3, 4) The winter ones tend to be jersey, easy to "top" up with a denim or other jacket or a sweater. I like to have at least two summer dresses of this type and one winter dress of this type. (I wear fewer dresses in winter.)
Travel worthy dress. (6,7, 8) There might be overlap with the MOTG category or even the occasion category here. But usually it will be jersey or a knit. I can wear on the plane, layered over and/or under. I can wear on trains, in the car, on buses. It will work with lots of different kinds of footwear.
At the moment, I have three of these. One is more "dressy" (a Kamalikulture ruched sheath) (8) yet I can throw it into a suitcase without worry about wrinkles. My other two are sleeveless shift type dresses that can be easily worn with tops under them as well as worn sleeveless with or without a topper. One's black and one is navy; very plain -- I can accessorize the yin/yang out of them. (6/7)
I also currently have a sundress/ special occasion day dress for summer -- because my main special occasion summer dress is so dressy, I have a pretty cotton dress that could take me to a daytime wedding or similar or to a casual date night. (9)
And those are my categories. Any extras, I know I won't wear, so I purge them. I could actually stand to purge a couple of these. I only wore the black jersey one in 7 twice or three times last fall/ winter and not at all in the summer (it's almost a year round dress for me -- but has seen a LOT of wear in other years and is showing its age). I rarely wear the blue knit in #6, either. And have not yet had occasion to wear the sundress in #9, which is starting to look a bit dated to me. So it might be on the chopping block.
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