Would You Let Your Bridesmaids Pick Their Dresses? (This Bride Did!)

gray bridesmaid dresses with yellow wedding shoes

Photo: Akil Bennett

What do real brides have to say about the wedding planning experience? Well, it's not all happy tears at the bridal boutique and indulgent cake tastings. Guest blogger Jennifer Castoro shares the pros and cons of "the first look," the ins and outs of throwing a winter wedding, and more.

I have a lot of bridesmaids. Nine, to be exact. (Technically there are seven, plus my sisters, who are my maid of honor and my junior bridesmaid, but whatever.) When it came time to choose my bridal party, I agonized over who to ask, mostly because I wanted to keep things simple and figured that would be easier with just an attendant or two, but I really, really wanted to have them all with me on my wedding day. What's the biggest day of your life without all your closest friends drinking early-morning champagne while jammed into a bathroom with curling irons and hair spray?

But attempting to outfit nine different people, with nine different body types, heights, skin and hair colors, and personalities, was not something I looked forward to. I have enough issues choosing dresses for myself—half the time I buy something, immediately regret it, and take it right back to whatever sale rack it came from (because heaven forbid I pay retail)—so I was totally freaked out by having to choose something that would work for all of them.

My solution was to let each girl pick her own dress. It seemed like a total win-win: They'd be able to choose whatever style they liked best and were most comfortable in—strapless, one-shoulder, sleeveless, ruched, you name it—and hopefully get some more use out of the dress post-wedding. (I also wouldn't have to settle on a dress that "worked" for everyone but wasn't necessarily a favorite.) I did want the look to feel cohesive though, so I knew I would have to set some guidelines.

So I took my sister/maid of honor, Jessica, who, luckily, has been willing to be a guinea pig for anything I want to try/test/reject, to a few bridal stores. We narrowed it down to a designer (Bill Levkoff), possible colors (blues, greens, or metallics), and length (cocktail), and I told my 'maids they could pick whatever they liked best. Copious online dress stalking and flurries of emails commenced. We set up a date for all the girls that lived locally to meet and try on dresses at a store in New York City, so they could see them all in person and I could give an opinion—if they wanted it, of course!

strapless sweetheart Bill Levkoff bridesmaid dresses

Photo: Courtesy of Bill Levkoff

But once everyone started trying all the different looks, there were no clear favorites. Some girls liked a strapless sweetheart (the two above were favorites), some a sleeveless V-neck, but nobody fell completely for any one particular style. They all put dresses on and looked at me like I was supposed to tell them what to pick, but honestly I just really wanted them to pick themselves. As they tried more and more styles on, I just got more and more confused, and basically ended up standing there repeating "I don't know..." in an increasingly desperate voice.

One of my friends, who I've known since kindergarten, pointed out a long strapless dress hanging on a rack nearby and asked what I thought about it. I'd initially wanted short dresses, the better for the girls to wear them again, but since I was mostly making that decision that for their sake, I was fine with a change of plans. We rounded up all the long dresses we liked and they tried a few on, and then we found it: a magical dress that not only looked great on every single girl, but was also just what I wanted—soft, romantic, and simple. (I don't want to reveal the exact Bill Levkoff dress we went with, but the Amsale bridesmaid dress below gives you a good idea of the silhouette and feel.)

Lavender Amsale long bridesmaid dress

Photo: Thomas Iannaccone

In the end, we decided as a group that all the girls would wear the same dress. It may not have been my plan initially, but I'm glad that they're happy with it (at least they seem to be!) and I'm happy that all my girls got to help me make one of the bigger decisions of the wedding day. Plus, it was a relaxed, fun night, and a happy memory I'll remember long after the dresses have been boxed up and packed away.

—Jennifer Castoro

Check back throughout the week to read more about Jennifer's wedding planning process, and get caught up with our other bride guests blogger, Anna Maltby.

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