The Ultimate List of Bridesmaid Proposal Ideas

Congratulations! You're engaged and it's time to call all of your best gals and show off your sparkly engagement ring! As you start planning your wedding day, it's important to think about who you want in your bridal party. After all, you'll want to ask them to be a bridesmaid sooner rather than later! Your ladies are always by your side, and when you're a bride, this won't be any different!

Before you ask your best friends to be your bridesmaids, we encourage you to send a thoughtful message to each girl to show them how much you care about them, love them, and remind them of how important your friendship means to you.

We know how special these best friend bonds are, so when it's time to ask the big question, you want to be prepared! That's why having a "Bridesmaid Proposal" is the cutest way to ask your girls to be your bridesmaids! With so many stylish items for all budgets that are fun and customizable, it's easy to find the perfect one to ask your bridesmaids with! 

Bride and Bridesmaids gathered together in the bridal suite, wearing floral robes and throwing confetti in the air.

Ball Photo Co Photography

*This post contains affiliate links through Etsy. While we can receive a commission through these links, opinions are entirely our own.

Bridesmaid Proposal Ideas Your Bridesmaids Will Love

Once you ask your best gals to be a part of your wedding, the fun will really begin! There are so many responsibilities that come with being a bride-to-be, and having your bridal crew by your side will be the best support system and a huge relief.

From here on out, these ladies will be by your side to help with your wedding. From the engagement party to the bachelorette party, the wedding dress shopping events, bridesmaid dress try-on's, and all the way to standing by your side on your big day, these ladies will be with you through it all.

Channel this excitement into a memorable bridesmaid proposal that your bridal crew will surely love and appreciate. And bonus, your bridesmaids can use all of these items for some ultra-cute pictures as they're getting ready on your wedding day!

Bridesmaids Proposal Ideas

Bridesmaids Proposal Box

Instead of choosing just one item for your bridesmaids, why not give your bridesmaids an entire box of bridesmaid goodies? These classy yet elegant boxes are sure to please your girls, and are undoubtedly the most popular way to pop the big question.

Even better, there are a huge array of options on the market. Regardless of your wedding budget or bridesmaids' personal style, you can find a bridesmaid proposal box that fits your needs. You can even find a box that aligns with your wedding theme or wedding color palette, with options like boho chic, modern minimalism, or even a rustic wedding.

Plus, there's even options for a Maid of Honor proposal box. There's no way your bridesmaids can say no!

pink bridesmaid proposal box

blue bridesmaid proposal box with robe

Maid of Honor Gift Box

Spa Products

Being a bridesmaid comes with a lot of stresses! From helping with the wedding planning to the wedding dress, dress try on's, hair appointments, and the bachelorette party, there's a lot going on as the wedding day countdown begins! This sentimental gift that will help your bridesmaids stay stress-free and relaxed throughout the entire bridesmaid process. After all, who doesn't love customized candles, face masks, boy oils, and sea salts?!

bridesmaid proposal spa box

Custom Totes & Bags

Now, this is a creative and useful bridesmaid gift! Ask your closest friends to be in your wedding party with a simple, customized accessory. Your options include classic totes, duffel bags, acrylic clutches, makeup cases, and more! These personalized tote bags are perfect for all of your girls, their cosmetics, and hair tools! On the morning of the wedding day, your bridesmaids will come prepared with all of their wedding day accessories! 

bridesmaid tote bag
bridesmaid duffel bag

bridesmaid makeup bags

bridesmaid acrylic clutch

Bridesmaid Proposal Glassware

Pop, fizz, clink! Whether it be for boozy brunch, happy hour, or a bridesmaids coffee date, how fun would it be to get your ladies together to pour a round of drinks and celebrate! Let each bridesmaid find the personalized message written on the side of trendy glass or personalized mug! Available in a wide variety of styles, a personal glass, coffee mug, or water bottle, is one of the best ways to ask your bridal party! We just know this would make the most fun celebration to ask your bridesmaids the big question: "Will you be my bridesmaid?!"

bridesmaid champagne flutes
bridesmaid tumblers

custom bridesmaid glass mug 

Bridesmaid Proposal Cards

With all the many greeting cards out there, Etsy is for sure the best selection when it comes to a wide variety of card options. Etsy offers so many creative wedding cards. From simple to funny, Etsy has served a wide range of different bridesmaid proposal cards. It's hard to pick a favorite!

For starters, there is the classic "Will you be my bridesmaid?" proposal card. More modern designs feature personalized details, like a bridesmaid proposal card with a vintage polaroid photo. You can even find custom artwork that looks like you and your bridesmaid on the big day, and this is one of our favorite styles of cards! It's so unique and something your bridesmaid can frame and save for years to come.

Another bridesmaid proposal card we love is one that features wedding details. Since your bridesmaid is technically a VIP and part of the wedding day, it's the perfect way to fill your bestie in on essential wedding details, before anyone else knows them! 

will you be my bridesmaid card

bridesmaid proposal card with polaroid

custom bridesmaid proposal artwork

bridesmaid proposal card with color palette

Bridesmaid Scratch-Off 

It's the ultimate surprise! Looking for a unique way to ask the big question? Of course... The biggest question has already been asked... We're talking about the next one in line - "Will you be my bridesmaid?!" A scratch off card is a cute and classic way to propose to your bridesmaids! There are lots of scratch-off bridesmaid proposal designs available on Etsy, so find the one that best aligns with your style. We've linked to one of our favorites below! 

bridesmaid proposal scratch off

Bridesmaid Proposal Floral Scratch Off Card

Scratch Off Will You Be My Bridesmaid Proposal Card

Bridesmaid Proposal Jewelry

Jewelry is a gift that any woman will appreciate, and perfect for a bridesmaid proposal. The best pieces of bridesmaid jewelry being simple and personalized items like a necklace or bracelet. Any item featuring their initial is sure to be a winner among your bridesmaids, plus they will be able to wear it time and time again.

We recommend opting for a durable metal, such as silver or gold, for longevity. Even better, we recommend gifting your bridesmaids a piece of jewelry that they can wear on your wedding day. Here at Kennedy Blue, we have some beautiful, affordable bridal jewelry with pieces perfect for your bridesmaids, too! Now, take a look below at our favorites and prepare your bridesmaids to have their accessories set in stone for your big day!  

initial bridesmaid proposal necklace
Kennedy Blue Jewelry Gold Clasp Bridesmaid Bracelet
initial bridesmaid proposal knot bracelet
Kennedy Blue Bridesmaid Teardrop Necklace Gold
Kennedy Blue Rose Gold Bridesmaid Earrings Square

Custom Travel Jewelry-Case

Planning a destination bachelorette party or a destination wedding? Then consider popping the question with one of these adorable custom travel jewelry cases! Many of them can be personalized with your bridesmaid's monogram, making them the perfect gift for your gals to keep for years to come! Made of high quality materials, a jewelry-case for your bridesmaids is a great gift to help your girls keep track of their jewelry when on any adventures... especially if they're a wedding event! 

bridesmaid travel case

Bridesmaids Travel Jewelry Box

Custom Bridesmaid T-Shirt

Want to ask your girls to be in your bridesmaid party and give them a trendy gift at the same time? Consider one of these beautiful bridesmaid t-shirts! Available in lots of colors and designs, your bridal party be able to wear them to a variety of your pre-wedding events, including your bachelorette party. Imagine how fun your getting ready wedding day pictures will look if all of your ladies are wearing the same personalized t-shirt?! 

custom bridesmaid shirt

Custom Bridesmaids T-Shirts

Custom Bridesmaid Jean Jacket

If you're willing to splurge a little on your friends, get them their very own denim jacket! After all, it's a classic piece that's going to be in trend forever. Every girl needs a denim jacket! You can even personalize the jean jacket with your bridesmaids' last name, a timeless phrase like "babe", or even a fun nickname! A denim jacket is an on-trend accessory that they will be able to rock time and time again. Including at the bridal shower, engagement party, or bachelorette party!

jean bridesmaid jacket

Customized Maid of Honor Jean Jacket or Denim Jacket

Personalized Bridesmaid Pajamas

Make sure your bridesmaids stay extra cozy when you gift them a personalized pajama set. If you're planning a fall wedding or a winter wedding, a cozy pair of customized flannel pajamas would make for fun photos! And for a summer or spring wedding, you can't go wrong with matching bridesmaids robes.

This adorable gift will work perfectly for an overnight bachelorette party, an event the day of the wedding, and especially if you're getting ready for the wedding day early in the morning.

Lucky for you, Kennedy Blue offers a variety of bride and bridesmaid pajamas sets, matching robes, and more! Plus, bridesmaid pajamas are a hit for creative Instagram posts! You have quite a few options, from oversized sleep shirts to trendy pajama sets. Browse some of our favorite personalized bridesmaids pajamas below! 

bridesmaid pajama set

bridesmaid sleep shirt

Kennedy Blue Bridal and Bridesmaid Pajama Set

Plaid Bridesmaids Pajamas

Satin and Lace Bridal and Bridesmaid Robes

Kennedy Blue Ruffle Bridal and Bridesmaid Robes 

Customized Hanger

Get your bridesmaids hangers they'll not only need to for bridesmaid dresses but will cherish forever, even after they put away their gowns. These personalized clothing hangers also serve another purpose, as they will look stunning in your getting ready for the wedding photos. Imagine hanging all of the gorgeous bridesmaids dresses on a clothing rack, with the personalized hangers as an elegant touch. What a classy gift to give your ladies! 

custom bridesmaid hanger

Personalized Bridesmaid Hangers

Custom Bridesmaid Wedding Hangers

Fuzzy Bridesmaid Slippers

Let's get cozy! Fuzzy bridesmaid slippers are a great solo gift, a good addition to a self-care bundle, or even a great gift to include in a Bridesmaid Proposal Box, similar to the ones we shared above. Featuring a soft and fluffy material, they will be your bridesmaids new go-to house slippers. Plus, who doesn't love personalized slippers?!

fuzzy bridesmaid slippers

Personalized Bridesmaid Slippers

Bridesmaid Scrunchies

A girl can never have too many hair ties! Scrunchies are simple, inexpensive, and something your future bridesmaids will be able to use for a long time. Sometimes, scrunchies are perfect for early morning wedding days, especially if they're waiting around to get their hair done. To make the proposal extra special, consider creating a personalized tag that features a little bridal humor.

bridesmaid proposal scrunchies

Silk Bridesmaid Scrunchies

Bridesmaid Scrunchies

Customizable Candle

It's time to set the ambiance! With cute packaging and a fun surprise inside, a candle is an excellent way to propose to your future bridesmaids! Every time they light the wick and smell the delicious scent, they are sure to think of you and the magical memories that they will make on your special day. We love that these candles are personalized and each bridesmaid will feel so special that you took time out of your day to create a candle label just for them! 

bridesmaid proposal candle

Bridesmaid Proposal Candle

Custom Bridesmaid Candle

Custom Bridesmaid Proposal Candle

Plant Pots

Are you and your girls plant lovers with green thumbs? Gift your best friend, future bridesmaid, and plant mom their very own personalized plant pot. Not only is this a gift your bridesmaids will cherish for years to come, but they make for the perfect shelf decor, too! And how sweet would these plant pots look in photographs?

These custom terracotta plant pots are cute and perfect for a small succulent or similar plant. If you're looking to get creative, plant something special and unique for each bridesmaid in the plant pots!

bridesmaid plant pots

Succulent Bridesmaid Gift

Personalized Bridesmaid Succulent

Bridesmaid Keychains

Everyone loves a new key chain, especially a personalized one! From acrylic keychains to leather keychains, we think keychains are the perfect, simple gift for your bridesmaids. Customized with your 'maids names, most of these keychains come with a ring for car keys, house keys, and other trendy decor.

bridesmaid keychains

Personalized Bridesmaid Keychains

Custom Bridesmaid Keychains

Custom Bridesmaid Keychains

Bridesmaid Proposal Cookies

What bridesmaid wouldn't want something sweet?! Just looking at these sweet and fancy bridesmaid proposal cookies, we're drooling at the sight! There is no way your friends can refuse a yummy treat, right? Ask your best friends to be in your bridal party by offering something that is sure to make their sweet tooth say, "YES!" 

bridesmaid proposal cookies 

Bridesmaid Proposal Cookies

Custom Wine Label

Place one of these glamorous wine labels onto your best friends favorite bottle of wine, and not only will it become a creative way to ask your bridesmaids, but it's a great way to celebrate together once they've said "yes!" You can get a label for specific roles as well, perfect for the Maid of Honor proposal. This would be a great bridesmaid gift along with one of the personalized wine glasses we shared above! 

bridesmaid proposal wine label

Bridesmaid and Maid of Honor Proposal Labels

Bridesmaid Proposal Wine Label 

Christmas Ornament

'Tis the season! What better time to pop the big question than during the Holidays? These glittery bridesmaid proposal Christmas ornaments are a lovely keepsake to hang it on their tree and remember year after year of that fond memory. These are absolutely perfect and fitting if you're planning a winter wedding, but if you're not, these will still make the perfect gift for your bridesmaid to bring out year after year. 

bridesmaid proposal ornaments

Bridesmaid Proposal Ornament

Maid of Honor or Bridesmaids Christmas Ornament

Personalized Bridesmaid Proposal

Confetti Poppers

Pop the question with these push-up confetti poppers that will have you and your friends laughing! The boxes are customized to feature each of your potential bridesmaids' names. And to find the surprise question, they'll have to sort through the colorful confetti. Imagine how magical this gift would be paired with a best friends photo shoot! This is one way to guarantee your future bridesmaids will have a blast!

bridesmaid confetti poppers

Floral Bridesmaid Robes

These stylish robes are excellent bridesmaid proposal gifts. Floral patterns are so elegant for your wedding day and we just know your bridal party will love these matching floral robes. Your bridesmaids will feel completely pampered when they're getting ready for your big wedding day, and for their at-home self-care sessions.


floral bridesmaid robes
Floral Bridesmaid Robes


Thinking About a Special Maid of Honor Proposal?

She's your best friend, sister, family, and she is your number one person to go to for everything. It's no question that she'll be right by your side leading up to your wedding day. Once you've decided whom you want to hold that honor of being maid of honor, it's your turn to ask the special question: “will you be my maid of honor?”

You are going to want to show this person how much they mean to you with something fun and creative, so instead of coming up with a list of items - we think it is essential to let you know that any of these bridesmaid proposal gifts are just as unique. There are plenty of customizable gifts to give to your future maid of honor, like the custom tote bag, a sparkly piece of jewelry, or even the customized maid of honor Christmas ornament. 

Kennedy Blue Maid of Honor Proposal Kennedy Blue Satin and Lace Bridal and Bridesmaid Robes in Sage and in White

How To Ask Someone To Be Your Bridesmaid

We all have those close friends, whether from childhood, our teenage years, or friends we met later on in life. Whether you're asking your best friend or family members to be your bridesmaids, there is nothing to be nervous about!

These girls have been with you throughout your life and would love nothing more than to support you as you marry the love of your life. You can ask each future bridesmaid all together in a group, or separately if you prefer time alone with each one of your gals. When it comes time to ask your ladies to be your bridesmaids, there are so many creative ways to do so! You've already said, "I do!" but what about your bridal crew?!

A bridesmaid proposal is our favorite way to creatively ask your girls to stand by your side. Whether you choose to gift each girl a bridesmaid proposal box, a pair of matching pajamas, or even with a customized wine bottle, there are a variety of ways to ask your ladies this special question. 

Kennedy Blue Bridesmaid Dresses in Teal

When to Ask Your Bridesmaids to Be In Your Wedding

Once you're engaged, you should begin thinking about who you want in your bridal party. If you have a clear list of ladies in mind, we say waste no time! It's fun to celebrate with your girls for as long as possible, so why delay the bridesmaids and maid of honor proposals?!

Ideally for planning, the latest you should ask your wedding party to stand by your side is 8 months to 1 year away from your wedding. This will allow time for your bridesmaids to help you plan, budget accordingly for all of the special wedding events like the bachelorette party, and allow you and them enough time to find the perfect bridesmaid dresses! Take advantage of this time to celebrate with your girls!

Kennedy Blue Bridesmaid Dresses in Dusty Sage SatinKennedy Blue Bridesmaid Dresses in Dusty Sage Satin


Now that we've covered a handful of bridesmaid proposal ideas and even a few maid of honor proposal suggestions, how do you plan to pop the question? All these ideas are bound to put a smile on your besties faces, and encourage them to say "Yes!" when you ask the question: "Will you be my bridesmaid?!"

Leave a comment below and tell us which bridesmaid or maid of honor proposal gift was your favorite! Have an idea of your own? Leave a comment below, to help other brides-to-be! We're in this together! Now it's time to maven to the next item on your wedding to-do list; checking out bridesmaid dresses. Head on over to our shop and browse our wide collection of bridesmaid dresses, featuring a variety of bridesmaids dresses in trendy colors, silhouettes, and designs.

Black Friday Sale: $99 Bridesmaid Dresses!

Most bridesmaid dresses are $99 (up to $50 OFF) + up to 55% OFF wedding accessories.


Leave a comment

July 28, 2021 09:12

Genius! I love these ideas, will be including a few in my proposals

April 14, 2021 16:13

I absolutely love these ideas for asking my girls! I can’t believe I didn’t think about a cosmetic bag or clutch, but that is perfect and can be reused! I think that, with some nail polish, hair ties like the above, and some other day of essentials would be perfect!

Shetavia Currie
September 21, 2020 10:45

These are awesome ideas! Definitely will be using a few of these.

July 19, 2020 15:51

Love all the ideas. Will be getting my proposal ready soon.

July 16, 2020 09:22

Love these!!! ❤️

Stephanie Langford
July 16, 2020 09:22

Love these ideas!!

Leah B
July 16, 2020 09:22

Thank you for all these amazing ideas

July 16, 2020 09:22

Love these ideas! I have been racking my brain for what I’m going to do for the bridesmaids proposal. I’m definitely leaning towards the personalized makeup bag.

Kristina Young
July 16, 2020 09:22

I’ve always loved the idea of a goodie Basket for a proposal. But my husband and I are a little weird, so instead of personalized champagne glasses, we want to do Ale Horns!

July 14, 2020 17:48

LOVE all of these!! I ordered custom boxes with each of my tribe’s name on them, included hair ties, a candle, a pen to take down any wedding notes, and then each gal got a special item just for them! <3

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