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How Do You Make Your Bridesmaids Happy with Their Dresses?

Could it involve more sequined and floral dresses? Please?


bridesmaid dresses from brideside

For years I’ve joked that despite working for APW, and having been a professional wedding photographer in a past life, I basically never go to weddings. Either my friends aren’t the marrying type, or they all live in major cities where the average nuptial age is closer to thirty-five. But this year the joke is on me, because I am going to not one, not two, but four weddings across the country, and I’m a bridesmaid in two of those. OKAY UNIVERSE, I SEE YOU.

Being up close and personal with so many people planning weddings this year has been a gentle reminder of just how hard it is when you’re a good person trying to wrangle a wedding party, especially when it comes to bridesmaid dresses. The questions I’m usually fielding these days are:

  • How can I make a half dozen (or an actual dozen if you’re my sister) people who have different bodies and tastes happy all at the same time?
  • Can I be laid back and still get the vision I want?
  • How do I avoid turning dress shopping into a full-time job?

Watters Bohemian Sleeves

My advice is usually the same: it’s actually easier to give people direction than it is to give free reign. Because even if you truly, genuinely don’t care what anyone wears, you’ll still probably end up fielding a bunch of questions (your people want to make you happy after all). Which means it’s totally fine if you just want everyone to wear the same thing (bonus points if that thing is considerate of their financial reality). But if you want your bridal party to have the freedom to choose their own outfits, one of the best compromises is to give some parameters, and then let them make decisions for themselves. And because my friends (sometimes) listen to my advice, that’s exactly what I’ve been tasked with for the two weddings I’m in this year. For one, it’s long black gown, preferably with some sparkles. For the other it’s something blush or gold, with sequins, beading, or lace. DONE AND DONE.

Technology to the rescue

And because the best part of working for a wedding website is knowing all the good shopping secrets, when it came time to actually get to brass tacks, that’s when I remembered APW partner Brideside. I originally went to Brideside after a bout of frustration trying to find a long sequin dress in a size bigger than twelve—almost all of Brideside’s dresses go up to a size 24, and some are even available from 00 to 30W. But then I recalled that Brideside lets you try on dresses at home before you buy. (Which is basically how I shop now, except typically I have to put hundreds of dollars worth of merchandise on my card and then return 90 percent of it to make it happen.) And since I’m three thousand miles away from being able to shop with my friends, and I’ll have a small baby in tow very soon, I am here for not having to leave my house. Plus I found these:

bridesmaid dresses from brideside

Sorella Vita Style 8848Jenny Yoo SloaneWatters DesireeWatters ElsonWatters Natasha Skirt and Zoe TankSorella Vita Modern Metallic Style 8686

And these, which are unrelated to my current dress search, but I need anyway:

bridesmaid dresses from brideside

Jenny Yoo Cassie Eden Bouquet PrintWatters FleuretteWatters AldridgeWatters LottieWtoo by Watters Style 303Jenny Yoo Claire

Brideside, it turns out, is also a godsend for procrastinators. When I signed up for my account, I was given the option to connect with a personal style consultant who will help me pick out dresses and make sure I order everything in time. I can save them to my digital closet, share them with my BFF and my sister, and schedule to have samples delivered to me to try on at home. Brideside also has a lovely little feature that gives you an estimated delivery date for every dress they sell. The last time I was a bridesmaid, I didn’t realize I needed to order my dress five months in advance, and when it almost didn’t show up in time for the event, I spent a week panicking. Instead, every time I log into Brideside, I’m reminded that I still have time, I do not need to figure it all out right now, everything will be fine. It’s like bridesmaid therapy.

JY embroidered 2017 dresses

but can you get what you want?

So now that I’m basically a professional bridesmaid (I kid, I know at least one of you is in, like, six weddings this year), I feel like I’ve cracked the nut on how to keep your people happy and yourself sane. And it looks something like this:

  • Speak your mind! Being a bridesmaid is a pretty well established social construct at this point. AKA, most people don’t go into it expecting you to give no f*cks. So speak them, and speak them clearly (and kindly).
  • But to the extent that you don’t care about certain things, give the people options. Especially if it means they can budget within their means, because I guarantee you, people care less about a dress they’ll never wear again, than about an expensive dress they’ll never wear again.
  • Use technology to your advantage. Part of the reason I went with Brideside is because of just how much handholding they do (and apparently Maddie the bridesmaid needs a fair amount of handholding or she forgets things). For example, their style consultants will pull together inspiration boards for mismatched dresses, liaise with your wedding on your behalf, make sure everyone orders their dresses in time, and basically acts as a proxy so that you don’t have to do all the nitty-gritty logistical work. They even have a section of their stylists’ favorite dresses to browse if you don’t feel like doing the heavy lifting of searching through dresses yourself. So to the extent that you can get help? Use. It.

Adrianna Papell Sequins

It’s easy to get caught up in trying to take care of your best people during wedding planning while also trying to take care of yourself. It means you’re probably a good friend. But what I’ve learned these last few months, is that it doesn’t have to be hard: know what you want, communicate it clearly, and then try to be flexible on the rest. You might end up discovering that your friends, like me, actually end up excited to drop some cash on fancy bridesmaid attire as a result. And if all else fails? Sequins help. Now who wants to help me choose a dress?

Have you been a bridesmaid recently? What’s the secret to keeping your wedding party happy? Or planning a wedding? What are your wedding party woes and concerns?


This post was sponsored by Brideside, the online dress boutique that takes bridesmaid dress shopping out of the salon and into the comfort of your own home. With a selection of hundreds of dresses, in size 00 to 30, and a team of dedicated style consultants Brideside hopes to make the dress shopping experience a more positive one for all your wedding party members. Click here to see some of their stylist favorites right now.

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