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I think it sounds like a cool idea. I think you can totally pull it off with the right accessories. They might appreciate the opportunity to pick things themselves so they can make the outfit even more their own. Also, I'm not sure what your vision is for the masks, but you could add rhinestones and/or feathers to them for added impact. Maybe the girls could get the simple black masks, but the kind with the stick on the side. They could carry those instead of bouquets.
I think that what you've described sounds very cool...I say go for it!!! It's visually cohesive, the girls will most likely be able to get lots of wear from those dresses in the future and it will certainly fit the theme / time of year.
And YES you can use jewelry to dress up any sort of dress! Let us know what accent colors you were thinking of an I'm sure the Hive can help you find some amazing options online! 
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Hi!
Thanks for all of your advice in advance-it's much needed at this point. My now fiance just returned from Iraq a month ago and we've decided to get married where he is stationed, Savannah, on October 31st. I am cramming a year's worth of planning into one month and one week and I am already going crazy! We are going to have our ceremony take place in one of the squares in Savannah at sunset and I want the whole feel of the night be romantic and dramatic. After we marry and have the reception in a courtyard of a compound we are renting, we are going to proceed to River Street for Halloween fun and I'm thinking of having my 'maids wear long black dresses and a simple black mask (the kind that is just around the eye area). So here's the deal-they don't all have the same body type...I'm thinking of having one of them in a braided halter maxi, one in a one shoulder ruffle maxi, one in a high front halter maxi, and one in a batwing maxi...I think I want the length to be long and dramatic because it will be perfect for the time of year and the day in particular. But, the dresses will be the jersey fabric...keep in mind this is a destination wedding with 4 bridesmaids and about 25 guests. Is it possible to use jewelry to dress up the dramatic maxi look or is this a long shot?? I tend to be a bit grandios in my thinking and then the reality doesn't always work out how I'd envisioned... Please give advice! I need you!