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There are several ways you can approach this: you can find a line (i.e. JCrew), pick a specific fabric, length and color, and then let your bridesmaid choose, or you can simply choose a color, send swatches to your bridesmaids and let them find their own (my friend did this, and they were all different lengths, styles and materials, but relatively the same color and it looked very nice), or you can pick the color and length (or just the length, or just the fabric) and let them find their own. There are many ways to do this! You just need to decide what you want to be similar and what you want to be different and go from there!
Depends on how "similar, yet different" you're looking for. I like a bit different as well, so I went to www.alfredangelo.com and chose 15, cocktail length, dresses in chiffon, and told my 5 bridesmaids to chose one and order it in the same color! Each dress is the same material, and length, but totally different style.
I had my 3 girls pick any long, lilac dress at David's Bridal. :)
We emailed ideas back and forth for months and then went once together to an alvina valenta trunk show. It's a year since we first started looking and my look is coming together exactly how I wanted-the theme was "bridesmaids on the runway" I want everyone to look seXXy and glamorous and love their dresses. I posted pics of the different dresses on this thread which also may be helpful to you.
http://boards.weddingbee.com/topic/pleasing-modest-and-fashionistas-with-the-same-dress
So I say first come up with a theme and go from there. I don't think you have to have the exact color and material to make it work-but pick a color that is going to really stand out AND be easy to find in case the girls don't pick a traditional BM dress, as none of mine have so far. It did seem overwhelming at first to me but it's been a lot of fun seeing what everyone picks.
Here is a picture of what I am going for....I probably got this off the wedding bee inspiration board! So cute!
resized_blackBMdresses.jpg (16.5 KB, 69 downloads) 2 years old 
I wasn't sure how to approach this either and thus hemmed and hawed for a bit. I ultimately chose a line (Jim Hjelm Occasions), a fabric (satin-faced taffeta), a colour (chocolate brown) and then narrowed it down to six styles from which the girls can choose (we will have four BMs..well, three BMs and a "groomswoman.").
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Help! I love the look of all different, but similar bridesmaid dresses....but I am just not sure where to start. Do you start with one dress you like and find others that look good beside it, or is it best to find a brand or a line and order different styles? I think that look is awesome, but just don't know where to start!