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The Ultimate List of Bridesmaid Proposal Ideas

Bridesmaid Pajamas

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! 

"Will You Be My Bridesmaid?" Proposal Ideas for 2024

Looking for bridesmaid proposal inspiration? Here are some of our favorite items to gift your bridesmaids during the proposal - from complete bridesmaid proposal boxes to adorable accessories. From here on out, these ladies will be by your side to help with your wedding. Including the bachelorette party, 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!

Kennedy Blue Gold Satin Bridesmaid Dresses

*This post contains affiliate links. While we may receive commission, opinions are entirely our own.*

1) Bride & Babe Iced Coffee Glasses

Iced Coffee Cups Bridesmaids

Bride & Babe Coffee Glasses

A personal glass or coffee mug 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?!"

2) Personalized Bridesmaid Proposal Cards

Will You Be My Bridesmaid Boho Cards

"Will You Be My Bridesmaid?" Bohemian Proposal Card

Create your own personalized message for each of your bridesmaids! They'll absolutely love the gesture, and the thoughtful words will make them feel extra-special.

3) 'Will You Be My Bridesmaid?' Candles

Bridesmaid Proposal Candle

Bridesmaid Proposal Candle

With cute packaging and a fun surprise inside, a candle is an excellent way to propose to your bridesmaids! 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!

4) Personalized Bridesmaid Proposal Box

pink bridesmaid proposal box

Personalized Bridesmaid 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.

5) Custom Bridesmaid Proposal Wine Label

Bridesmaid and Maid of Honor Proposal Labels

Custom Bridesmaid Proposal Wine Labels

Place a wine label on your friend's favorite bottle of wine for a great way to celebrate together once they've said "yes!" You can get a label for specific roles - perfect for the Maid of Honor proposal.

6) Custom Travel Bridesmaid Jewelry Cases

Bridesmaid Jewelry Case

Personalized Bridesmaid Jewelry Cases

Planning a destination bachelorette party or a destination wedding? Consider popping the question with an adorable custom travel jewelry case! 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!

7) Bridesmaid Pajamas (for Getting Wedding-Ready)

Kennedy Blue Bridal and Bridesmaid Pajama Set

Matching Bridesmaid Pajamas

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. Add these adorable pajamas to a bridesmaid proposal box - we promise they'll love it!

8) Build Your Own Bridesmaid Proposal Box

Bridesmaid Proposal Boxes

Build-Your-Own Bridesmaid Proposal Boxes

Or, you may prefer to build your own bridesmaid proposal box! Add in the exact items you want for each bridesmaid to make it more personalized. Get started with a cute box, and go from there!

9) Floral Bridesmaid Proposal Cards

Bridesmaid Proposal Cards

Floral 'Will You Be My Bridesmaid' Cards

If you want to keep your bridesmaid proposal sweet and simple, consider giving a proposal card! Writing a thoughtful message on what your bridesmaid means to you & how you are grateful for her means more than you think.We're loving these adorable pink 'will you be my bridesmaid?' cards! Order for a bridesmaid, maid / matron of honor, or flower girl!

10) Boho Bridesmaid Proposal Box

Bridesmaid Proposal Box

Boho Bridesmaid Proposal Box

Featuring a thoughtful bridesmaid proposal card, cute personalized tumbler, and more - this complete bridesmaid proposal box is perfect! All you have to do is write in the card. Your bridesmaid s will think the whole box is adorable!

11) Custom Bridesmaid Mirror Compact

Bridesmaid Compact Mirror

Personalized Compact for Bridesmaids

Perfect to have on the wedding day for touchups, these adorable mirror compacts are a perfect gift to include in your bridesmaid proposal box! Available in different colors and with the option to personalize - your bridesmaids will love these!

12) Bridesmaid Scrunchies Proposal Gift

'I Can't Tie the Knot Without You' Bridesmaid Scrunchies

'I Can't Tie the Knot Without You' 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. To make the proposal extra special, consider creating a personalized tag that features a little bridal humor.

13) Bridesmaid Makeup Bags with Names

Personalized Makeup Bags

Personalized Makeup Bags

Another cute (and practical!) gift for your bridesmaids is a personalized makeup pouch! Get these fun canvas bags personalized with each girl's name with a heart at the end.

14) Custom Bridesmaid Jean Jacket

Bridesmaid Jean Jackets

Customized Bridal Party Jean Jackets

If you're willing to splurge a little on your friends, get them their very own denim jacket! You can even personalize the jean jacket with your bridesmaids' last name, a timeless phrase like "babe", or a fun nickname! A denim jacket is an on-trend accessory that they will be able to rock at the bridal shower, engagement party, or bachelorette party!

15) Customized Fuzzy Bridesmaid Slippers

Bridesmaid Fuzzy Slippers

Personalized Bridesmaid Slippers

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

16) Personalized Bridesmaid Proposal Tumbler

Personalized Bridesmaid Tumbler

Custom Bridesmaid Tumbler

A perfect bridesmaid gift that keeps giving! These personalized tumblers are adorable for getting wedding ready - but your girls can use them even long after the wedding!

17) Dainty Gold + Pearl Bridesmaid Necklace

Bridesmaid Proposal Jewelry

Gold + Pearl Bridesmaid Necklace

For a darling, elegant touch - this sweet gold and pearl necklace is perfect! Plus, it's a beautiful piece that your bridesmaids can wear often after the wedding day!

18) Personalized Bridesmaid Keychains

Custom Bridesmaid Keychains

Personalized Bridesmaid Keychains

A cute and practical gift for a bridesmaid proposal! Choose up to 10 characters to spell out names, wedding titles, or other meaningful words! Your bridesmaids will love this little gift.

19) 'I Couldn't Tie the Knot Without You' Bracelet

Bridesmaid Proposal Bracelet

Bridesmaid Proposal Bracelet

A fun take on bridesmaid jewelry, this cute tie bracelet is a fun option! Adjustable to fit a variety of sizes, your bridesmaids will love this adorable bracelet.

20) Custom Bridesmaid Totes

Bridesmaid Totes

Custom Bridesmaid Tote 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!

21) Wedding Details Bridesmaid Proposal Cards 

Wedding Details Proposal Card

Bridesmaid Proposal Cards with Wedding Details

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!

22) Personalized Bridesmaid Sleep Masks

Bridesmaid Sleep Masks

Bridesmaid Sleep Masks

Perfect for an overnight bachelorette party - or for a sleepover before the wedding day! These super cute bridesmaid sleep masks can be personalized to have their names or wedding titles (i.e. bridesmaid, flower girl, etc.) Add it to a bridesmaid proposal box!

23) Bridesmaid Proposal Cookies

Custom Bridesmaid Proposal Cookies

Will You Be My Bridesmaid? Cookies

What bridesmaid wouldn't want something sweet?! 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!"

24) Custom Bridesmaid T-Shirt

Retro Bridesmaid Shirt

Retro Bridesmaid Shirt

Want to ask your girls to be in your bridesmaid party and give them a trendy gift at the same time? Consider bridesmaid t-shirts! Available in lots of colors and designs, your bridal party can wear them to pre-wedding events, including your bachelorette party.

25) Bridesmaid Proposal Christmas Ornament

bridesmaid proposal ornaments

Bridesmaid Proposal Ornaments

'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.

26) Personalized Bridesmaid Hanger

Bridesmaid Proposal Hangers

Bride & Bridesmaid Hangers

Get your bridesmaids hangers they'll not only need to for bridesmaid dresses but will cherish even after they put away their gowns. These personalized clothing hangers will look stunning in your getting ready for the wedding photos. What a classy gift to give your ladies! 

27) Bridesmaid Proposal Plants

bridesmaid 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! 

Considering 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?”

Kennedy Blue Maid of Honor Proposal

Satin and Lace Bridal and Bridesmaid Robes

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. 

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?!

Kennedy Blue Bridesmaid Dresses in Teal

Kennedy Blue Bridesmaid Dresses in Forest Green

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.

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?!

Kennedy Blue Bridesmaid Dresses in Dusty Sage Satin

Kennedy Blue Bridesmaid Dresses in Dusty Sage Satin

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!

Time to Ask 'Will You Be My Bridesmaid?"

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.

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Leave a comment

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

Allison McMillan
July 14, 2020 17:48

Cute ideas. I was looking for a list like this.

Kassandra Boyce
July 12, 2020 21:47

What cute ideas!!

July 12, 2020 21:47

Definitely some super cute ideas in here. Didn’t realize you needed to propose to your bridemaids.

July 12, 2020 21:47

These are great! My bride asked me to be her bridesmaid by taking me out to Olive Garden. She’s my best friend 😊

Laura T
July 12, 2020 21:46

I’ve been looking at bridesmaid proposal ideas for awhile and this blog gave me so many more! Love the t-shirt idea. It’s a cute proposal but then they can wear it at the bachelorette party!

July 12, 2020 21:46

The scratch off cards are so cute! I think I might go with the matching robes, because they can be used as the bridesmaid proposal, the bachelorette slumber party, and for the wedding day!

July 12, 2020 21:46

Super cute helpful ideas!

Victoria Bobholz
July 12, 2020 21:46

LOVE the necklaces!

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