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14 Proposal Boxes That Will Impress Your Groomsmen

by Tyler Carter April 27, 2020

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 14 of the best groomsmen proposal boxes that will impress your guys:

14. To the 9's Tripack

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."

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. Groomsmen Proposal Bomb

    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! 

    11. 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!

      10. 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. 

      9. 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.

      8. 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.

      7. 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.

        6. 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.

        5. 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. 

        4. 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.

        3. Midnight Smoker

          Cigar Groomsmen 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!

          2. 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! 

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