How do i match my bridesmaids dresses without making them uncomfortable?

It’s great to have the comfort of your bridesmaids in mind but at the end of the day it is your wedding! Any true friend will wear a literal trash bag for you on your wedding day if you asked them hahaha! In all seriousness, perhaps you should choose a few different styles that you like and let the maids give their input to help narrow them down. Call a meeting and show them “I picked dresses A, B, C, and D. I want us all to match so let’s find one from these options that everyone is ok with wearing.” You’re still giving them a little bit of choice, but from a selection that you picked. So you’ll still get the look you want and they’ll feel like they had a say in what they wear.

I suggest going with a website such as Azazie, Kennedy Blue, or Birdy Grey that all have a set of named colors that all their dresses come in. First, pick the color you want. Second, pick maybe 3 or 4 styles you would be cool with any of the bridesmaids wearing. Third, tell your bridesmaids the dress color on that website you have chosen, but that they can wear style A, B, C, or D as long as it is in that color. Have them submit your choices to you by a certain date, then you order them all at once (this is very important so that they all come from the same dye lot) and then collect payment from each bridesmaid.

On Azazie(and probably other sites) you can make a show room. You could pick your color and have your girls look at dresses they like and add them to which you can yay or nay it.

However I like Erin's jdea that you pick a couple styles and have them look. If they're the same color same fabric and similar cuts no one would notice and your bridesmaids would feel more comfortable.

You have to know the people that you're asking to be in your wedding party. Pick out the dresses or dress that you would like for that person(s) to wear and that fits their personality.

I realize I'm lucky that all my bridesmaids are near, but we all went together to look at bridesmaid dresses and it kind of worked out that they all felt comfortable when they tried on the same dress.

Dresses I've found that work on many body types are long, looser skirts, a defined waist, but with either ruching or a looser bodice, and either sleeves or wide straps- no tugging up a strapless dress and no weird underarm/upper boob poking out that I always seem to get with thinner straps.
Picture of my bridesmaids in the same dress attached

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This is what I did. Once I figured out what color I wanted for the bridesmaids, I picked 3-4 dress styles that I thought would work for the season, the venue, and would be a fairly universally flattering choice. My bridesmaids all ended up liking the same style, so that made it easy.

If you want to give them some flexibility, you can tell the they're welcome to pick their own shoes (recommend this regardless, but it's nice to let them know you care about them feeling good and being comfortable).