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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  • savannnah

    Just in case this post is actually for crowd sourcing your dress pick for the gold dress wedding- I think you would look amazing in the Watters Elson dress.

    • Maddie Eisenhart

      THAT’S THE ONE I WANT. I just need to reconcile the open back situation. WHY did it need to be an open back, why?

      • Jane

        I would love to love open back, but I HATE all the front only bra options.

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        • Maddie Eisenhart

          But now that I’m being swayed, I wonder if I could hem the bottom and use the extra fabric to make a sort of makeshift back that would cover a bra strap? IDEAS, I HAVE THEM.

          • Jane

            If you can do it, more power to you and your awesome tailor. But I would make sure you can do that (or can accept it without the changes) before committing to it. I know sometimes it’s harder alter beaded dresses (I bought one of those gorgeous long beaded Adrianna Pappel dresses for super cheap somewhere but had to give up on it because getting it hemmed was going to cost more than twice what I’d paid for the dress).

            You had A LOT of beautiful options. So, no reason you HAVE to go with this dress, even though it was obvi gorgeous.

  • Helen Yan

    A quick note about giving guidelines to your bridesmaids. It can be nice to just suggest a color- but make sure it’s a color that people can find! I was in a wedding a few years ago where we had a color scheme to follow, and it seemed like it was going to be easy, but it was actually pretty difficult. It was a time where every dress in every store was either coral or mint….and neither of those were what I was looking for. So if you’re hoping for a color that’s out of season or not currently a big trend, it’s probably easier to just pick a dress rather than giving people free reign.

    • savannnah

      Yes I ran into this issue as the bride picking the color. I wanted dark teal and everyone kept sending me pictures of green dresses. So I just scoped the web for a month and pinned 75 dresses to a board and they picked from those. It was a happy medium but I also had the time to do it.

    • sofar

      Same goes for shoes. “Bright purple” is one of those wtf kind of colors. The only shoes I could find in that color were super uncomfortable. Please, brides, just pick “gold” or “nude” or “black” or “silver.”

      • Amy March

        Ewwwww pls don’t pick a specific shoe!

        xoxo, those of us with picky feet

        • Jessica

          co-signed, person who spent $75 on a pair of ill fitting terrible shoes she wore for 2 hours.

          • Kate

            This, and mine were unflattering to boot

          • Jess

            Same, and the dye they used on the shoe bled all over my feet. I had a feeling it would not work well in advance, so I brought some flats and changed immediately following the ceremony.

      • PAJane aka Awesome Tits

        Weird color? Dyeable shoes to the rescue!

    • NolaJael

      YES. I was in a wedding about 10 years ago where the bride said “anything in forest green” which is not a super common color and definitely has variations. Mix and match wasn’t as trendy then as it is now, so what happened is the first girl bought a dress at David’s Bridal then everyone else just followed suit because they weren’t sure what to do (and online shopping has come a long way since then). So “anything” turned into “Davids’ Bridal” in a hurry (not knocking DB, just that wasn’t the original idea).

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    • I think that was the season of my wedding! I hate the stiff, dowdy, pricey dresses at bridal shops and I wanted people to be able to shop to their price point and body type. I told them turquoise or jade dresses because I had a peacock feather theme, and it was a nightmare. Then all the guests showed up in mint, and looked more like they matched than some of my bridesmaids. I really really wish I had been more relaxed about it, for the low-key wedding I had telling them something summery in blue or green family would have worked out just fine, and it was so unnecessarily difficult for everyone involved to find a very particular shade.

    • Maddie Eisenhart

      Yes, and also, if you ARE picking a hard to find color, that’s when it can be most helpful to just pick a brand of dress and let people choose from within it. Because it’s often easier to find those weird colors in traditional bridesmaid dresses than in off-the-rack stuff.

    • Kyle Hutchinson

      Yeah, last time I was a bridesmaid we were told we didn’t have to wear, like, a *bridesmaid* type dress so long as it was long and navy. Sadly, the options that year in “long and navy” were knit beach cover-up maxi dresses and… bridesmaid dresses.

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  • Amy March

    Love Brideside! So much easier than repeatedly texting my sister all the long navy gowns with straps I like.

  • Her Lindsayship

    These dresses are AMAZING. I’m not anyone’s bridesmaid this year but I might just get one for my bachelorette or rehearsal dinner or like for lounging around my apartment. I mean dang.

    I ended up going with a different site for my bridesmaids because they needed to go a little cheaper than these, but I was definitely drooling over some dresses at Brideside before that. Anyway, the online bridesmaid dress game is strong these days! I just said, ‘pick any knee-length dress from this site in dark green’ and I think each of them is genuinely excited about her dress of choice! At first I was a lot more fluid about it, but eventually it was clear that it would be much easier to just give them direction – and I only have two bridesmaids! I can’t imagine twelve.

  • sofar

    I told my bridemaids, “Pick a dress, any dress, in any solid color you desire.” I literally did not care. They ended up in kelly green, mint, coral, fuchsia and royal blue. One had just given birth and was relieved that she could just pick up a dress that fit her last minute. Another changed her mind at the last minute when she lost weight. I had been in too many weddings where someone doesn’t fit in their dress the day before and there are Problems because it has to be a specific dress. My bridesmaids were just able to run to the store two days before and take care of their issues instead of bothering me about it.

    But if you DO play the “wear whatever you want” game, you have to be comfortable with making things super broad. No “wear whatever you want, but make sure it’s knee length, peach and has lace” or “wear whatever you want, but please make sure it’s navy or marigold and that you plan among each other to make sure half of you wear marigold and half of you wear navy.”

    • Alli

      Your last paragraph is so spot on. I was going to ask my girls to all just wear any navy dress. Then I saw a picture where 3/4 bridesmaids were wearing midnight blue dresses and one was in a true navy. It bothered me, I’m not someone who can handle it! So I just took the girls to an Alfred Angelo and said “we’re getting navy dresses here, pick a style you like” and they seemed pretty happy with that.

    • Maddie Eisenhart

      Yes, and if you do play the “wear whatever you want game” you have to MEAN it. I tried that, and like the commenter below realized I didn’t mean it! So I assigned specific colors to everyone. Even then, I probably should have given more direction. But know thyself.

    • nutbrownrose

      I think I’m kind of being that pain in the ass, because I gave my girls 4 shades of blue and said “A-line, knee-length, floaty dress with at least 2 straps that aren’t halter.” Because I was gonna say “Not strapless,” and then my mom came up with more restrictions. And then they all picked royal blue. So I’m sorry. I tried. I truly wanted them to have the option to shop at Ross or Goodwill and find a dress that suited both them and their budgets. It has sort of worked, because one got hers for like $12 on Etsy, and another went to a bridesmaid shop. I also gave them more than a year to shop because of the saying “Fast, Good, Cheap. Pick 2.”
      I’m back and forth and still feeling anxious about this, clearly. But my MOH is also getting married this year and picked one dress at David’s, it’s long, $160, and impossible to wear a normal bra with. And I hate it. It was easy, but I would have preferred the chance to shop with restrictions, which is why I did what I did.

      • Maddie Eisenhart

        Honestly, your parameters don’t seem crazy to me. I can easily think of a handful of dresses that would work, and blue is pretty popular year round. Don’t stress about it!

        • nutbrownrose

          Thank you! I’m mostly just an insecure anxious wreck in need of validation, so thank you for giving me that. Nevermind that all my bridesmaids said of course they would do it, but I thought they were just humoring me and willing to move heaven and earth to do the impossibly difficult.

  • K.

    Honestly, this is probably a downer on these GORGEOUS dresses but…my bridesmaids prioritized very clear direction on what to wear (matching dresses) and at least one nearly cried in happiness that I chose an option that was <$100 (not sure if the service I used is a competitor to Brideside so I won't link or name here)

    It helped that the dresses were pretty, but they were ultimately about the practicality of it. Though to be fair, they were all also traveling to my wedding and taking at least 2-3 days off work for me, so finding easy, cheap, flattering dresses was the least I could do. But extra glitter and sequins would not have excited them in the least if it would have added to their time management and bottom line.

    Know your people!

  • CMT

    I’ll take one of each of the sequins, please.

  • Jane

    For me, one of the hardest parts about looking for bridesmaids dresses for my friends was that I loved all the dresses and just wanted to buy them for myself. I do not think Brideside would help with that problem. ;)

    I had a specific vision in mind so I did a lot of internet searching and gave my bridesmaids specifc options or the choice to send me any options they thought would work. Everyone ended up going with dresses I picked out, so I did most of the work. But I also looooved it. And I was able to get dresses in a wide range of prices. I think 3 of the 7 were under $100 and the other 4 were pretty spread out between $100-$200. As beautiful as the Brideside dresses are, it seems like it would be hard to work with friends’ budgets the same way.

  • louise danger

    easiest way to remove bridesmaid dress hassle: i have one person on my side of the bridal party. no worries about different body types, dye lots, mismatch-on-purpose, etc.

    i told her “pick something in a warm purple [like eggplant or plum] that feels the same in look/formality as the rest of the wedding” and she wound up with a wrap dress from an online retailer whose sleeves and length she was able to customize – like that other commenter, i dunno if they’re a competitor of Brideside so i won’t link/name them here.

  • JC

    I had an amazing experience with a consultant picking out my dress for my sister’s wedding. I’m a terrible shopper, so we built ourselves a list of criteria that helped narrow everything down.
    Step 1: Does it look maybe interesting on the rack? Pulled about 20 dresses, lots of colors.
    Step 2: Is it flattering? Tossed most, kept maybe 4-5.
    Step 3: Does it come in the correct color? I brought a swatch of sister’s preferred fabric. (This could be question #1 if you were ordering online.)
    Step 4: Can it be ordered in time and get alterations?
    Step 5: Which one would sister like best? It’s her wedding, so if I think it’s flattering, and she’d like it, then we’re both happy.
    In the end, there were three dresses that were contenders, and only one came in the exact color. It could be ordered in time, and she would like it. Boom, that was my dress. I sent her a picture and she GUSHED. This is now my go-to bridesmaid guide.

  • There are definitely perks to the UK system where the bride pays for all the bridesmaid gear, though it does make it hard to coordinate (I want you to pick a dress so I can pay for it is surprisingly hard to do when you’re on opposite sides of the country). I wish Brideside did try ons for international customers too – I entirely get why they don’t (transatlantic shipping can take forever, and there are so many surprise charges!) but I don’t think I could risk buying dresses that expensive without the girls getting to try them on first.