17 Great Ways to Propose To Your Groomsmen

by Tyler Carter May 08, 2020

Getting the girl was the easy part.  Now you have to assemble an all star group of men that you will call your groomsmen.  Coming up with a great way to propose to these men will be worth the effort. The next question is how do you make asking them to be your groomsmen something they will remember forever?

 We are here to help you with some ideas on how you you can pop the question to your fearless groomsmen. It’s key that your groomsmen proposal is unique and creative and is unlike any other proposal your guys may ever experience. We put together 17 creative groomsmen proposal gifts that can help you ask your groomsmen.


17. Personalized Groomsmen Bow Tie

Hand him this elegant looking bowtie that comes with a personalized card as you ask him to be a groomsman. The bowtie is made of 100% polyester/gabardine that’s very smooth to touch. It has an adjustable necklace and comes in navy or black. This gift includes a white mailer box so it’s ready to be given as a gift.

16. Scratch Off Card

It’s no ordinary card. The creative side is that you’re giving him a clue that it’s time to suit up with that bow-tie design and a scratch-off card that will do the asking for you. It’s really one unique and classy way of asking him to be by your side on your wedding day. The card is made of white smooth heavy card stock and a black paper bow tie is attached to the front of the card with volume stickers. Watch the look on his face as he scratches off and read what’s written on this card. 

15. Monogrammed Suspenders Fancy Clip


Ask it with his suspenders ready for your rustic themed wedding. Let him stay classy with this personalized suspenders. This gift comes with his embroidered initials in black or white thread depending on the color of his suspenders. You also have the option to choose from a variety of thread colors that will go with your wedding motif. It is made of 100% woven plastic polyester and comes with an adjustable button and an adjustable clip-on with the finest 2 leather details before the clips. You can also have it beautifully packaged in a gift box to make it extra special for your groomsman.   

14. 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!

13. Personalized Wooden Watch

    With an accessory he can readily wear for your wedding day, you’re sure to get a resounding yes to make him one of your groomsmen. This personalized wooden watch is made of 100% authentic wood with no added chemicals. It features a Japanese quartz movement with a classic and simple design. It’s durable and long-lasting you can be sure your groomsman will be able to use this for a long time on any occasion. It even has a 12-month warranty and offers repair services. Each watch comes in an eco-friendly box and ready to be handed to your groomsman.  

    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."

    11. Engraved Golf Ball Markers Divot Tool

    His love for golf is obvious. And what better way to ask him to be your groomsman than to give him this wood golf ball marker with his name or initials. He will surely love this stylish custom engraved 3-in-1 golf ball marker and divot tool. Choose from walnut wood, oak wood, or black metal material for the ball markers. It’s sleek and practical and definitely the best way to ask your golf aficionado friend to stand with you on your wedding day. This gift is packaged in a custom engraved gift tin box ready to be handed to your groomsman.    

    10. Pigskin for Him 

    Engraved Groomsmen Mini Football

    Weddings in the fall are great, don't get me wrong. The weather is beautiful, and the temperature is great. But weddings on a Saturday or Sunday in the fall mean that someone is going to miss watching their team play. It's not the end of the world. Give the nod to their dedication to you with their own personalized football. This is one of the best groomsmen gifts for the younger members of your wedding party.

    9. Bamboo Shot Set

    Engraved Groomsmen Shots and Flask Set

    All nights that start with let's do shots is an interesting one. Now you either take those shots like a champ or you spend the next day trying to remember how you ended up in a random bathtub in a pink leotard. 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. 

    8. Paul Bunyon Box 

    Engraved Axe, Shot Glass, Label Gift Set

    Ripping shots and chopping trees down, that is what men do. We took these manly core values and applied them to an amazing gift set. That set became the Paul Bunyan Box! This box set 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. Broposal Label 

    Proposing to him need not be a pressured or awkward moment. Let these Broposal Label do the asking for you. Give one of these labels and let the booze do the talking! Sized to fit most 250 ml liquor bottles (Bottle not included), so you can match your men up with their favorite beverage, these labels will help seal the deal. It's one of the easiest and simplest ways to ask your buddies to stand by your side.

    6. Proposal Pack

      Proposing to your groomsmen has never been easier than with this personalized gift box set. This Proposal Pack perfect for your groomsmen as a gift when you propose to them or just thank them for being part of your wedding. Packed 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. 

      5. 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.

      4. Time to Suit Up

      Let this gift be your way of saying how thankful you are for all his help and support. This box set comes with a custom low-ball glass, (1) 4oz premium soy candle, gold credit card style bottle opener, maple bourbon flavored toothpicks, a custom liquor label, and a pack of playing cards. This Time to Suit Up is one gift that your best man will truly appreciate.  

      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. 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! 

      1. Fashion Hour

      Engraved Groomsmen Fashion Set

      This set has everything you could need and will need for that special day. Humidor for cigars with the guys, fun socks to make those tight new shoes bearable to dance in. Your photographer will love the shades for photos and the watch will keep your groomsmen on time after they polish off the engraved flask.  

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