Discover the perfect way to pop the question with our curated collection of groomsmen proposal boxes. Say "will you be my groomsman?" in style.

36 Proposal Boxes That Will Impress Your Groomsmen

Saying "I do" won't be possible without your groomsmen standing beside you.

Asking your best buddies and family members to be your groomsmen should not just be another task to do on your list. You just got to ask them to be your groomsmen in a way that is out of the ordinary for your groomsmen. The idea of a groomsmen proposal box set right in front of him is the perfect way to ask him to be your groomsmen. 

Surprise your groomsmen by adding a fun card inside the box that does the proposing for you, and make sure you get no less than a resounding yes with the proposal gifts he will find inside the box.  

Here are 36 of the best groomsmen proposal boxes that will impress your guys:

36. Groomsmen Proposal Watch Set

Groomsmen Proposal Box Time To Suit Up Watch Set

When it comes to time to choosing your groomsmen propose to them with something they will be able to use for years to come. This classy watch will serve your groomsmen well on your wedding day and throughout your groomsmen's adventures. This handsome watch is made with real sandalwood and genuine leather. With a 45mm face this is one handsome watch that any guy will greatly appreciate. It comes in a slick wooden box all you need for the perfect bro-posal. Get down on one knee to make the moment complete.

35. Wearable Groomsmen Proposal Box

Wearable Groomsmen Proposal Box

Ask your best friends to back you up, and give them some style with this unique groomsmen proposal box.  Proposing to your groomsmen has never been easier than with this personalized gift box set. The perfect gift if you are looking to give your guys a gift when you ask them 'Will You Be My Groomsmen?'.

34. Rotating Groomsmen Proposal Box

Rotating Groomsmen Proposal Box

It's time to get down on your knee once again to recruit your boys to be there on your big day.  With this rotating groomsmen proposal box, you will be able to "pop the question" easier than ever before.  Make sure your Groomsmen arrive at your wedding in style wearing these stainless steel role personalized cuff links. The rotating box helps you reveal the secret inside, and will also allow them to store their cuff links and remember your wedding for years to come! 

33. Midnight Smoker

    Cigar Groomsmen Proposal Gift Set

    The Midnight Smoker gift set is a mix of a stay at home humidor and smoke anywhere travel set. The full set comes with a wallet, an engraved Zippo lighter a personalized travel case, and a stainless steel cutter. The cutter can be carried on the back of the case for quick and easy cutting and lighting. There's no better proposal gift for a cigar lover than this one. You can easily prove that with that big smile on his face the moment he opens this gift!

    32. Shoot Your Shot Groomsmen Proposal Box

    groomsmen proposal box set

    Any of your groomsmen to be will swoon over this groomsmen proposal box set. This groomsmen box set comes with everything you and your guys can need for a perfect bro-posal. Pre-fill the flask with your groomsmens favorite liquor and make sure your phone is out for documented proof. Once he takes that shot and sees the big "YES" at the bottom of the glass he will know this is a sworn oath not to be taken lightly.

    31. The Indecent Groomsmen Proposal

    groomsmen proposal gift box

    You popped the question once, now you need to get down on one knee for your guys. No sweaty palms about this proposal though, no guy can say no to this groomsmen boxed set. Filled with items your groomsmen can you use from the bachelor party to the big day and beyond, this 5 piece set is the perfect way to get your best friends to stand beside you as you marry the girl of your dreams.

    30. Bro-posal

    groomsmen gift box with shot glass

    So you have got down on one knee and the woman of your dreams has agreed to marry you, now its time to pop the question to your guys. This Broposal Gift Box is just the right tool for the job, none of your guys can resist this proposal. This set comes with a personalized shot glass, as well as a label to apply to your guys favorite half pint of any liquor, both enclosed in a sleek black engraved box. Cap it all off and join your guy in taking a shot together, how much more romantic can you get.

    29. Golf Ball Groomsmen Proposal

    Golf Groomsmen Proposal

    This "will you be my groomsmen?" gift set includes a customized golf ball inside the box that says, “let's par-tee” on it.  It is an awesome groomsmen proposal idea if we bonded over our mutual enthusiasm for golf.

    If you're looking for a classy combo that works magic in numbers, this To the 9's Tripack box set collection is a trio that will sing sweet music to any of your groomsmen. In the flick of a box top, you can propose to your groomsmen with a set of metal accessories that will take any suit to new heights. This classic groomsmen gift set comes with links, a money clip, and a tie clip that will splash formal wear with the needed touch. Put them in this awesome box and personalize all three and you are all set to getting a resounding "yes."

      27. Groomsmen Proposal Bomb

      Groomsmen Proposal Box Personalized

        Proposing to your groomsmen has never been easier than with this Proposal BombPacked neatly inside the personalized pinewood box you'll find a knife and a shot glass. The top of the box is personalized with the name and the inside of the box is personalized with his name and role. There's no way he can refuse to be part of your wedding party with this amazing gift! 

        26. Groomsman Kit

        Getting a kit like this would guarantee his big "yes!" This Groomsman Kit includes a clear Acrylic mug with ""Cheers"" design, a Cigar cutter, Beverage sleeve with ""Groomsman"" design, bottle opener keychain, black sunglasses with "Groomsman" on side. Don't forget to take a good shot of how he reacts upon seeing this gift!

          25. Wooden Chess 8OZ Brown Leather Hip Flask Set

          This Wooden Chess 8OZ Brown Leather Hip Flask Set includes a 1 piece Hip Flask, 1 piece funnel,2 pieces of 1oz cups he can use to  share drink with friends anywhere and a fashion leather style, gift box packing. It's one gift that can be enjoyed with your best buddies while playing the common game you play - chess. 

          24. Complete Men's Gift Set

          No is the last word he will have in mind when you hand him this Complete Men's Gift Set. This set includes a men's watch, sunglasses, cufflinks, tie clip, groomsmen gift set, groomsmen gift box, wedding party gifts, multi tool, black gift box, Tuxedo set, black tie, black flask, and bottle opener. This stylish gift box is sure to amaze your groomsman to be. 

          23. Engraved Bullet Box Groomsmen Gift Set

          Each of these Engraved Bullet Box Groomsmen Gift Set includes a custom engraved black hip flask, a whiskey glass, tactical hatchet, and recycled bullet box. These Tactical hatchet packs a 3mm thick black steel blade, Pakkawood handle, and a rugged sheath. It's one brilliant groomsmen gift for him who likes to camp and drink with their best friends. 

          22. Time To Suit Up Round Gift Box

          groomsmen suit up gift box

          This gift box is a call to action to your groomsmen. Like Superman and Batman they are needed and must report for duty. So assemble the squad and get ready. This box comes with a custom low-ball glass, a premium soy candle, bourbon flavored toothpicks, gold credit card style bottle opener, a pack of playing cards, and a custom liquor label to fasten to the favored drink of your groomsman. The box is fully customized and looks great on display after removing the contents.

          21. Everyday Tactical Groomsmen Gift Box 

          This everyday carry set comes with an engraved pocket knife with a spring-assisted blade and attached belt clip.  Also included is a carbon fiber minimalist wallet with RFID (wireless theft protection). The tactical ballpoint pen doubles as a flashlight when the need arises. Throw in a custom flask and your groomsman has his everyday essentials covered. All this in a handsome wooden keepsake box.

          20. Personalized Whiskey Gift

          This Personalized Whiskey Gift comes with 2 personalized whiskey glass and personalized whiskey decanter in personalized wood box. The box measures 7.5” x 5.” x 4” and is made from wood of high quality. The glass is made from premium lead free glass and can hold up to 10 ounces while the decanter can hold up to 17 ounces. 

          19. Premium Bullet Sharped Whiskey Stones Gift Set for Men

          It's a must have gift for your groomsmen. Putting ice in your whiskey dilutes the spirit and robs it of its rich flavor and subtle aroma. He deserves to enjoy the mature taste of an old single malt or the dashing sweetness of bourbon with these JUMBO stainless steel ice cubes / whiskey rocks. With a secret non-toxic gel inside them, they’ll keep the consistency of his drink intact. The Premium Bullet Sharped Whiskey Stones Gift Set for Men is one proposal gift he won't easily forget. 

          18. Cigar Gift Box

          It's that one box he will surely reach for when he wants to have a cigar and a drink. With this Cigar Gift Box you can put inside some cigars or a mini bottle of whiskey personalized specially for your groomsmen. It comes personalized with his name and his favorite quote. The gift box can also be customized. 

          17. Personalized Flask 


          This Personalized Flasks are a great gift for your groomsmen. It comes in 5 different colors and 9 engraving options to make this a perfect proposal gift. The flask and case are made from durable, yet soft water-resistant, easy to clean leatherette. Shots funnel are made of stainless steel. It also comes in a magnetic gift box ready to be handed to your groomsmen.

          16. Groomsmen Proposal Set of 5

          Get your groomsmen pumped for your big day! The Groomsmen Proposal Set of 5 includes a stylish hip flask, a can cooler, a gift bag, 80s-style groomsman sunglasses, and a stainless steel straw. Let him drink his favorite beer in style. The groomsmen gifts bundle includes a can cooler which is made of neoprene that expands, contracts, and keeps chilled beverages ice cold. The stainless steel 8oz. hip flask is perfect for holding all types of liquor. It may be engraved to add a personal touch, and is packed in an elegant wooden gift box. It also comes with a Tuxedo gift bag and tons of coolness with it. 

          15. Suit Up Custom Groomsmen Proposal Box

          The best way to ask your best bros to stand by you is with this custom groomsman proposal gift box. It comes with a flask, a black bow tie, and a custom greeting card all inside a personalized wooden gift box. The box can be personalized with two lines of text of your choosing while the greeting card comes in four different styles where each can be customized with a title and name. Your bros will all be pleasantly surprised and honored when you present them with this incredible groomsman proposal gift box! 

          14. Groomsman Gift Box


          The Groomsman Gift Box contains 1 personalized custom engraved gift set with flask with additional options for folding pocket knife, engraved lighter with tin case and rosewood gift box. Your best buddie swill truly be delighted with this proposal gift. 

          13. Groomsmen Box Set 

          Gentlemen Box Set

          Ask your groomsmen with this Gentlemen's Box Set that comes with a personalized minimalist wallet and 6 oz.  flask, all enclosed in a keepsake wood gift box. This front pocket, a minimalist wallet is made of high-quality aluminum and stores 1 to 12 cards without bending. Additionally, it has a secure exterior clip for bills. It's one gift you can be sure they carry all the time way after your wedding day.  

          12. Black Leather Wallet & Cufflinks Gift Set


          It's one handsome gift that can be personalized for the special men in your life. This Black Leather Wallet & Cufflinks Gift Set is not too difficult to find when you want the best for someone. It's sure to bring a smile on his face knowing his superior taste when it comes to shopping.Gift boxed with custom foam packaging, you are all set to giving one awesome gift!

            11. Bamboo Shot Set

            Engraved Groomsmen Shots and Flask Set

            All nights that start with let's do shots is an interesting one. Let him know you want him to be part of your wedding party with this Bamboo Shot Set. This gift set is a great mix of party and style, a sleek flask that holds 6 oz of your favorite elixir and two shot glasses to share the fun with friends. Whether you are discretely pregaming before the ceremony or throwing back shots with the bride and groom, this box will keep the party going. 

            10. Cigar Tube Flask Gift Set

            This Cigar Set is a wonderful gift and perfect for asking him to be one of your groomsmen. Set in black silk lined gift box, it includes a cigar tube, cutter, and lighter - everything he would need to enjoy a relaxing moment. This gift is of high quality and has a precise and beautiful engraving that makes it even more special. This is one gift you can be sure he will use for a very long time.

            9. Irvine Groomsmen Flask Gift Box Set

            The Irvine Groomsmen Flask Gift Box Set is a triple-threat of total enjoyment. It features an exciting sleek, black stainless-steel beverage flask, handsome corkscrew/bottle opener, and a natural wooden keepsake box. This exceptional groomsman gift is an alluring collection with a mix of standard engraving and personalization that will surely please him from day one.

            8. Paul Bunyan Gift Box

            Engraved Axe, Shot Glass, Label Gift Set

              Ripping shots and chopping trees down, that is what men do. These manly core values are embodied in this amazing gift set. The Paul Bunyan Box is for a group of friends that love to kick back outside and stick some steel to pine. Get your groomsmen a gift that will blow their minds when they open the box. They will love it so much they couldn't turn you down.

              7. Slice & Buzz 

              The alluring appeal of this Slice & Buzz is simply undeniable. Let your groomsman enjoy this custom gift box to safely store his valued items. It's the perfect gift set to ask him to be part of your wedding party. The box is also a humidor add a cigar in it and you are all set to give him the ultimate gift.

              6. Suit Up Set 

              Ask your groomsmen to stand with you and complete the look with this accessory gift box set. This classy combo is the perfect way to assemble your ultimate groomsmen squad while getting them looking the part. The boxes feature one pair of socks, cuff links, a tie clip, and 'Time to Suit Up" insert all packaged in a kraft gift box and sealed with string. Your groomsmen will appreciate wearing this set on your big day and for years to come.

              5. Personalized Pint Label

              groomsman proposal liquor label

              Slap one of these personalized labels on your guys favorite liquor, hand him a shot glass and bro-pose( your choice if you get down on one knee). These personalized labels will fit any half pint. Go the extra mile and bring a great shot glass for him.

              4. Action Hero Gift Box Set

              Hero Gift Box Set

              This Action Hero Gift Box Set gift comes with a cigar humidor, a cool pair of shades, a classy watch, and a flask you always need to get a little loaded. Lastly, it comes with a personalized knife that he can pull out at the last second to cut the red wire. This complete gift set is packed with everything he needs to be a ripped action hero. 

              3. VIP Gift Set 

              Get him this 5-in-1 gift set that contains everything that’s essential to your groomsmen. This set contains an awesome personalized flask for his favorite drink, an 8.5-inch bottle opener, a slim body aluminum minimalist wallet, and a black steel pocket knife. You even have the option to get them all or just choose the items you want to be included in the gift box. All this is placed in a VIP package ready to be handed as a perfect proposal gift.

              2. Man of the Hour

              Man of the Hour

              A flask, a bottle opener, a shot glass, and a knife. This Man of the Hour box set has everything your groomsman needs to be the man of the hour for years to come. With so many tools for use in this box, you’ll equip him to take a shot, save the day with an opener, share with a friend, and defend his honor all in one. This box set is a great option as a proposal gift that has everything he will surely enjoy. 

              1. Personalized Rosewood Finish Flask Gift Set

              He's up for more serious fun with this Personalized Rosewood Finish Flask Gift Set as you ask him to be one of your groomsmen. This set includes (1) 7 oz stainless steel flask,(1) stainless steel funnel, (1) stainless steel shot glass,(1) pack of playing cards, and 5 dice. There's just no way he won't say a resounding "yes" with this gift! 

              Groomsmen Proposal Cards