16 Great Groomsmen Proposal Gifts

by Chris Bajda December 16, 2020

You are with your groomsmen day in and day out. But this time it's will totally be a new season you'll be facing in your life. Getting married and having all your best buddies standing right next to you would make your special day even more unforgettable. Propose to your groomsmen and ask them to be part of your wedding party with gifts that say how much you value their friendship and how it would be an honor to have their presence on your wedding day. 

Whether you choose a groomsmen proposal gift set or individual gifts that bear his name or monogram for your groomsmen proposal gift, he will surely treasure whatever you give him for the rest of his life.

Here are 16 groomsmen proposal gifts you can choose from: 

16. Bounty Hunter

Let them be a treasure-seeking pirate as you give this classic gift.  Your gang of groomsmen will be elated to receive this chest of riches.  Adorn your groomsman with a humidor, knife, flask, and wallet to secure his cash, all personalized to their liking.    

15. The Indecent Groomsmen Proposal Gift

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.

14. Personalized Rosewood Finish Flask Gift Set

They'll be up for more serious fun with this Personalized Rosewood Finish Flask Gift Set as you ask them to be 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 they won't say a resounding "yes" with this gift! 

13. Personalized Whiskey Gift

It comes with 2 personalized whiskey glass and personalized whiskey decanter in personalized wood box. This Personalized Whiskey Gift  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. 

12. Complete Men's Gift Set

There will be no reason to say no as 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. 

11. Personalized Phone Stand Wallet

It's a personalized wallet that doubles as a phone stand. The Magic Man Wallet and Phone Stand comes with 2 secure pockets for his cards and cash. The slim grip slides shut to keep his pockets slim. 

10. Groomsmen Proposal Set of 5

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.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. 

9. Visol Barclay Personalized Travel Humidor 


The Visol Barclay Personalized Travel Humidor will carry up to 10 of his favorite cigars. This humidor will keep his treasured items safe wherever he goes. The cedar interior holds in moisture to create a comfortably humid environment. Outside, a polished black finish shines with reflection. It comes with free engraving of his name or initials on this cigar case. 

8. Proposal Rustic Dark Grey Vintage Premium Card


This Proposal Rustic Dark Grey Vintage Premium Card is printed on high quality card stock paper. This groomsman and best man proposal card comes with a matching ivory white envelope and ready to be folded. A personalized message can also be written inside with plenty of space to share your thoughts with your friends and family.  

7. Spiral Your Proposal to Your Groomsmen

Groomsmen Proposal Football

It's a gift that won't fumble on his big weekend. Your groomsman will feel like a Super Bowl MVP when you toss a perfect spiral with this cool personalized football. It's one gift you can be sure won't disappoint. 

6. Give Them Socks To Wear on Your Wedding Day

Groomsmen SocksIt would be a nice addition to your man’s wardrobe collection. These personalized groomsman socks add a fun and personal touch to wedding fashion. Let your wedding party enjoy this gift for your groomsmen proposal and everyone will be on the same page. Socks are an obligatory gift for men on all occasions, but groomsmen socks are perfect for this once in a lifetime event and will look amazing in those wedding pictures. 

5. A Bottle of Booze with a Custom Label

Groomsman Proposal Booze Label

The BroLabel is the perfect way to ask your buddy that important question. A bottle by itself is the most pedestrian of gifts, but slap on a label that personalizes the flask like it’s only meant for your groomsmen. Treat your favorite guys to a bottle of their favorite sauce, but with a message they can’t ignore.

4. Cigar Gift Box

This Cigar Gift Box is one he will surely reach for when he wants to have a cigar and a drink. With 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. 

This To the 9's Tripack box set collection is a trio that will sing sweet music to any of your groomsmen. You can propose to your groomsmen with a set of metal accessories that will take any suit to new heights. Put them in this awesome box and personalize all three and you are all set to getting a resounding "yes."

2.  Irvine Groomsmen Flask Gift Box Set

These exceptional groomsman gifts are an alluring collection with a mix of standard engraving and personalization that will surely please him from day one. 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. 

1. Baseball Bat Beer Mug 

Baseball Bat Mug

This baseball bat mug will really cheer them on. It's the love for the game of baseball that bonds your friendship them. Whether your team is kicking off Spring Training, or chasing the pennant in October, all you really need are your best buddies standing with you on your wedding day. 

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