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Groomsmen Proposal Gifts

Groomsmen proposal gifts make asking your friends to be groomsmen a double whammy of honor. If you’re looking for a creative idea for your groomsmen proposals, start with one of these meaningful gifts.

Our shoppers have found a ton of success with their groomsmen proposal gifts when they customize a message on their gift. It’s a way to say “I love you, man” without the awkwardness of literally saying those words to his face.

Every gift you will find here is customizable. Whether it’s cufflinks or a bottle that’s ready to hold your groomsmen’s favorite whiskey, go above and beyond when asking your best friends to be a part of your wedding day.

Personalized Groomsmen Insulated Trail Coolers Set of 5 - Holds 12 Pack Personalized Groomsmen Insulated Trail Coolers Set of 5 - Holds 12 PackOn Sale
$ 145.99 $ 182.99
Personalized Groomsmen Duffel Bag - Gym Bag-Travel Gifts-JDS-Black- Personalized Groomsmen Duffel Bag - Gym Bag-Travel Gifts-JDS-Black-On Sale
From $ 32.99 $ 40.99
Personalized Cooler Chairs - Set of 5 - Insulated - Groomsmen Personalized Cooler Chairs - Set of 5 - Insulated - GroomsmenOn Sale
$ 199.99 $ 249.99
Groomsmen 12-Pack Trail Cooler With Built-In Bottle Opener Groomsmen 12-Pack Trail Cooler With Built-In Bottle OpenerOn Sale
$ 34.99 $ 43.99
Personalized Groomsmen Heavy Canvas Duffel Bag-Travel Gifts-JDS- Personalized Groomsmen Heavy Canvas Duffel Bag-Travel Gifts-JDS-On Sale
$ 47.99 $ 59.99
Personalized Sit N Sip Cooler Groomsmen Gift Personalized Sit N Sip Cooler Groomsmen GiftOn Sale
$ 39.99 $ 49.99
Personalized Bullet Lowball Whiskey Glass Personalized Bullet Lowball Whiskey GlassOn Sale
$ 19.99 $ 24.99
Engraved Groomsmen Pocket Watch-Executive Gifts-JDS- Engraved Groomsmen Pocket Watch-Executive Gifts-JDS-On Sale
$ 33.99 $ 41.99
Personalized Can Cooler - Beer Can Cooler - Groomsmen Gift-Default- Personalized Can Cooler - Beer Can Cooler - Groomsmen Gift-Default-On Sale
$ 21.99 $ 27.99
Personalized Groomsmen Leather/Canvas Toiletry Bag-Travel Gifts-JDS- Personalized Groomsmen Leather/Canvas Toiletry Bag-Travel Gifts-JDS-On Sale
$ 34.99 $ 43.99
Personalized Groomsmen Duffel Bag - Travel Bag-Travel Gifts-JDS- Personalized Groomsmen Duffel Bag - Travel Bag-Travel Gifts-JDS-On Sale
$ 55.99 $ 69.99
Engraved Harmonica Stainless Steel Hohner Harmonica-Executive Gifts-JDS-Default- On Sale
$ 18.99 $ 23.99
Personalized Cufflinks - Gunmetal - Round - Groomsmen Gifts-Cufflinks-JDS- On Sale
$ 25.99 $ 31.99
Personalized Flasks - Gift Set - Shot Glasses - Black - Groomsmen Gifts-Antler- Personalized Flasks - Gift Set - Shot Glasses - Black - Groomsmen Gifts-Antler-On Sale
$ 26.99 $ 33.99
Personalized Camouflage Cooler Chair  - Sit N' Sip Personalized Camouflage Cooler Chair  - Sit N' SipOn Sale
$ 31.99 $ 39.99
Personalized Flasks - Cigar Case - Combo - Stainless Steel - Groomsmen-Default- On Sale
$ 25.99 $ 31.99
Personalized Cufflinks - Pin Stripe - Silver - Monogram - Groomsmen Gifts-Default-Silver- On Sale
$ 26.99 $ 33.99
Personalized Flasks - Set of 5 - Glass - Groomsmen - 8.5 oz.-MoonShine- Personalized Flasks - Set of 5 - Glass - Groomsmen - 8.5 oz.-MoonShine-On Sale
$ 114.99 $ 143.99
Personalized Cufflinks - Silver - Round - Groomsmen Gifts-Default-Silver- On Sale
$ 25.99 $ 32.99
Personalized Cufflinks - Gunmetal - Square - Groomsmen Gifts- On Sale
$ 22.99 $ 32.99
Personalized Whiskey Decanter - 2 Lowball Glasses - Decanter Set Personalized Whiskey Decanter - 2 Lowball Glasses - Decanter SetOn Sale
$ 47.99 $ 59.99
Personalized Whiskey Decanter - Glass - 23 oz. Personalized Whiskey Decanter - Glass - 23 oz.On Sale
$ 34.99 $ 43.99
Personalized Black Flasks & Lighters - Gift Set of 5-Flasks-JDS-2Lines- Personalized Black Flasks & Lighters - Gift Set of 5-Flasks-JDS-2Lines-On Sale
$ 161.99 $ 201.99
Personalized Golf Shoe Bag - Embroidered-Sports Gifts-JDS- Personalized Golf Shoe Bag - Embroidered-Sports Gifts-JDS-On Sale
$ 28.99 $ 35.99
Personalized Flasks - Personalized Lighters - Set - Groomsmen-Flasks-JDS-2Lines- Personalized Flasks - Personalized Lighters - Set - Groomsmen-Flasks-JDS-2Lines-On Sale
$ 42.99 $ 53.99
Personalized Coolers - Soft Sided - Personal Cooler Personalized Coolers - Soft Sided - Personal CoolerOn Sale
$ 37.99 $ 46.99
Personalized Flasks - Cigar Case - Lighter - Combo - Groomsmen - 1.5 oz.- On Sale
$ 42.99 $ 53.99
Personalized Cufflinks - Silver - Oval - Monogram - Groomsmen Gifts- On Sale
$ 26.99 $ 33.99
8 oz. Leather Flask with Folding Shot Glass-Default- 8 oz. Leather Flask with Folding Shot Glass-Default-On Sale
$ 25.99 $ 32.99
Personalized Canvas Supply Weekender Duffel Bags - Set of 5 Bags-Khaki Personalized Canvas Supply Weekender Duffel Bags - Set of 5 Bags-KhakiOn Sale
$ 229.99 $ 299.99
Personalized Canvas and Leather Shaving Travel Bags for Groomsmen - Set of 5- Personalized Canvas and Leather Shaving Travel Bags for Groomsmen - Set of 5-On Sale
$ 166.99 $ 208.99
Personalized Growler - Beer - Amber Glass - 64 oz.- Personalized Growler - Beer - Amber Glass - 64 oz.-On Sale
$ 18.99 $ 23.99
Set of 5 Groomsmen Whiskey Decanters - 23 oz. Set of 5 Groomsmen Whiskey Decanters - 23 oz.On Sale
$ 131.99 $ 164.99
Personalized Groomsmen Canvas Shaving Kit-Travel Gifts-JDS- Personalized Groomsmen Canvas Shaving Kit-Travel Gifts-JDS-On Sale
$ 28.99 $ 35.99
Personalized Set of 5 Camouflage Cooler Chair - Sit N Sip Personalized Set of 5 Camouflage Cooler Chair - Sit N SipOn Sale
$ 151.99 $ 189.99
Personalized 2-in-1 Cooler Duffel Bag for Groomsmen-Default- Personalized 2-in-1 Cooler Duffel Bag for Groomsmen-Default-On Sale
$ 34.99 $ 43.99
Personalized Can Coolers - Black - Stainless Steel - Groomsmen Gifts-Stamped Monogram- Personalized Can Coolers - Black - Stainless Steel - Groomsmen Gifts-Stamped Monogram-On Sale
$ 20.99 $ 25.99
Personalized Sports Weekender Duffel Bag - Set of 5-Blue- Personalized Sports Weekender Duffel Bag - Set of 5-Blue-On Sale
$ 175.99 $ 219.99
Personalized Flasks - Stainless Steel - Groomsmen Gifts - 4 oz.-Default- On Sale
$ 23.99 $ 29.99
Personalized Cufflinks - Set of 5 - Round - Gunmetal - Groomsmen Gifts- On Sale
$ 122.99 $ 153.99
Personalized Cufflinks - Set of 5 - Pinstripe - Groomsmen Gifts-Silver- Personalized Cufflinks - Set of 5 - Pinstripe - Groomsmen Gifts-Silver-On Sale
$ 135.99 $ 169.99
Personalized 6 oz BlackSilver Flask Gift Set for Groomsmen-Stamped- Personalized 6 oz BlackSilver Flask Gift Set for Groomsmen-Stamped-On Sale
$ 26.99 $ 33.99
Personalized Backpack Travel Cooler - 24 Can Capacity Personalized Backpack Travel Cooler - 24 Can CapacityOn Sale
$ 30.99 $ 38.99
Personalized Bullet Lowball Whiskey Glasses - Set of 2 Personalized Bullet Lowball Whiskey Glasses - Set of 2On Sale
$ 39.99 $ 49.99
Money Clip & Wallet for Groomsmen-Black- Money Clip & Wallet for Groomsmen-Black-On Sale
$ 17.99 $ 21.99
Personalized Whiskey Decanter - 4 Lowball Glasses - Decanter Set Personalized Whiskey Decanter - 4 Lowball Glasses - Decanter SetOn Sale
$ 78.99 $ 98.99
Personalized 6 oz Rustic Gold Flask Gift Set for Groomsmen-Modern- Personalized 6 oz Rustic Gold Flask Gift Set for Groomsmen-Modern-On Sale
$ 26.99 $ 33.99
Personalized Leather Travel Shaving Travel Bag-Default- On Sale
$ 40.99 $ 50.99

Fun Groomsmen Proposal Gifts

Consult our guide on how to propose to your groomsmen for the best groomsmen proposal ideas. If you already know how you’re going to ask, but you need to the gifts for execution, consider the following — our best groomsmen proposal gifts ideas:

  • Cufflinks
  • Whiskey decanter
  • Weekender bag
  • Cigar case
  • Flask & lighter set

These gifts are not only thoughtful, but they can give your future groomsmen a glimpse into what’s in store for the wedding. Is it a super formal, black-tie affair? Cufflinks. Destination wedding? Weekender bag. Amazing view from the rooftop of the wedding venue? Cigar me, please.