18 Great Groomsmen Proposal Boxes

by Chris Bajda January 23, 2022

Finding the best gift box set for your groomsmen proposal is not easy. After all, you are asking your best buddies to stand beside you on your wedding day. Your groomsmen deserve a well thought out proposal gift for being your go to men. Make sure you pick a box set that will surprise them, but also impress them. Choose a proposal box set that will tell them how much you know them, something they can wear on your wedding day or something functional for your regular get together.  

Here are 16 of the best groomsmen proposal boxes that you can choose from: 

18. Take a Shot Groomsmen Proposal Box

Groomsmen Proposal Box Set

This groomsmen proposal box set comes with everything you need to propose to your best men , or at least make an unforgettable impression. Give the guys in your life a shot with this great gift set. 

17. Time to Suit Up Groomsmen Proposal Box

Time to Suit Up Groomsmen Proposal Box

This stylish watch will be worn for years to come.  Propose to your groomsmen with a gift box that is both practical and fun. You'll get yes's all around, especially if you go down on one knee again.  


16. Star Wars Whiskey Decanter Set

Letting him know that you appreciate him and his hobbies would mean a lot to him. You know he's into STAR Wars collection right?  Then appreciate even his nerdlike love for Star Wars and add this Star Wars Whiskey Decanter Set to his collection then ask him to be part of your wedding party. 

15. Dude Doctor 

This Dude Doctor will be sure to put smiles on your groomsmen faces. It is a personalized groomsmen gift box meant to deliver. It comes with a wood gift box engraved with a laser from a stellar and flexible finish. The box can include the pictured flask and knife, knife nicely sitting in the crisp paper. Asking him to be your groomsmen has never been this easy.  

14. Mug Shots 

It's been his life long fantasy to be a gangster. Let this funny gift of Mug Shots of six of America's most notorious gangsters make his dream come true! Each shot glass has a front and profile mug shot of a famous gangster. Ask him to be your groomsman with this gift that includes six 2 ounces shot glasses in colorful packaging.    

13. Mandalorian Groomsmen Gift 

He is an official Mandalorian Groomsman as you hand him this Mandalorian Groomsmen Gift. Leave an impression that lasts forever with this gift. You can be sure you'll be putting a big smile on his face and you'll never have to ask if he's in or not.  This is one of the most unique groomsmen gift ideas out there.

12. Broposal Cufflinks

groomsmen proposal cufflinks

Let those man tears flow with this dressed up groomsmen proposal gift. Pop the question by giving him this rotating cuff link proposal box. Get your guys geared up for your big day in style with this high class groomsmen gift. Want to make it extra special, ask him by getting down on one knee.

11. Tell Them It's Time to Suit Up

groomsmen proposal gift set


Pop the question to your favorite guys while making sure they don't look like slobs on your big day with this slick groomsmen set. He surely won't be able to resist the idea of joining your debonaire looking squad. Watch the smile grow ear to ear as you pop this groomsmen set in front of him.

10. Take them to a Cigar Lounge

Get them a personalized cigar gift. Go to your favorite cigar lounge and place a note to each of their cigar choices, asking them to be your groomsman. Having all the guys in one spot without any distractions will allow you to relive old memories, and thank them for always being by your side. 

9. Personalized Toiletry Bag

Help him get organized and ready for your destination wedding with this personalized toiletry bag. Made of 100% genuine cow leather, this Dopp kit’s interior is waterproof and made of nylon cotton blended fabric lining. This item and the box can be personalized with his name or initials to make it extra special. No need to wonder if you will get his resounding "yes" with this gift. 

8. A Cuff Is Enough


A Cuff Is Enough is more than enough to melt his heart that you have chosen him to be part of your wedding party. Decorate his wrist with a gift that is tangible, a gift that brings manliness with an ever chunky right angle. With this dazzling duo, you bring that accessory that brings some metal to your man's formal wear. 

7. Personalized Leather Wallet

    He will be delighted to know that this tri-fold wallet is personalized and uses RFID blocking material. It is made of soft and genuine top grade cowhide leather. This personalized men’s wallet is very slim and comes in a variety of colors to choose from: brown, black, toffee, indigo and antique saddle. The wallet has provision for driver’s license, 7 slots for cards, 2 slots for keys and 2 compartments for receipts, cash, and checks. This is one gift that will always remind him how you thoughtfully asked him to be your groomsman.

    6. The Potent Shareable

    The Potent Shareable is a custom engraved gift set that comes with a flask, four shot glasses, a funnel, and folding pocket knife, housed in a black presentation box. Both the flask and knife are customizable with an engraving of your choosing. You can never go wrong with this gift as you ask him to be your groomsman. 

    5. All The Right Cuff

    This All The Right Cuff has everything you need to get a resounding "yes" from him. It comes with a sleek wood wrist watch and wood cufflink set.  The watch is constructed from durable bamboo wood and leather straps, manufactured with high-quality Japanese made quartz movements. Engrave 3 or 4 lines on the back of this timepiece and you have one awesome gift he simply can't resist. 

    4. Ultimate Man Pack

    This Ultimate Man Pack is a perfect gift for asking him to be your groomsman. It includes a personalized whiskey glass, slate coaster, and whiskey stones. The best part is you can engrave them all. It's a groomsmen gift that he will truly be delighted about. 

    3. Debonair Deluxe

    He only deserves the best. This Debonair Deluxe contains top quality that spells luxury and elegance. This set of premium necktie complete with a tie clip and a pair of cuff links will let him get that perfect polished look. All items except the tie can be personalized with his name or initials. It is quality, style and affordability wrapped up in a luxurious gift box. Simply perfect as you ask him to be your groomsman. 

    2. Cheap Shot


    This Cheap Shot is a 2-ounce shot glass in a beautifully engraved wooden box. Both items can be engraved to present your gift with amazing personalization.  This baby might be small, but it packs a serious gifting punch your guy won't expect. Needless to say, he will be part of your wedding party in no time at all.  

    1. Spider Whiskey Glasses Set 


    They are the superheroes of your life. And you just cant say "I do" without them. Ask them to be part of your wedding party with this Spider Whiskey Glasses Set. It's a personalized gift  that includes a decanter, and whiskey glasses in a wooden gift box. Made to order, each of them will be personally engraved for your groomsman. 

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