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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 PackSold Out
$ 138.99 $ 182.99
Personalized Set of 5 Groomsmen Cooler Chairs Personalized Set of 5 Groomsmen Cooler ChairsOn Sale
$ 155.99 $ 249.99
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
Groomsmen 12-Pack Trail Cooler With Built-In Bottle Opener Groomsmen 12-Pack Trail Cooler With Built-In Bottle OpenerSold Out
$ 37.99 $ 43.99
Personalized Sit N Sip Cooler Groomsmen Gift Personalized Sit N Sip Cooler Groomsmen GiftOn Sale
$ 39.99 $ 49.99
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 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 Camouflage Cooler Chair  - Sit N' Sip Personalized Camouflage Cooler Chair  - Sit N' SipOn Sale
$ 31.99 $ 39.99
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 Whiskey Decanter Set with 2 Lowball Glasses Personalized Whiskey Decanter Set with 2 Lowball GlassesOn Sale
$ 57.99 $ 59.99
Personalized Cufflinks - Gunmetal - Round - Groomsmen Gifts-Cufflinks-JDS- On Sale
$ 26.99 $ 32.99
Personalized Flasks - Cigar Case - Combo - Stainless Steel - Groomsmen-Default- On Sale
$ 25.99 $ 31.99
Personalized Whiskey Decanter - 23 oz. Personalized Whiskey Decanter - 23 oz.On Sale
$ 37.99 $ 43.99
Personalized Black Flasks & Lighters - Gift Set of 5-Flasks-JDS-2Lines- Personalized Black Flasks & Lighters - Gift Set of 5-Flasks-JDS-2Lines-Sold Out
$ 161.99 $ 201.99
Personalized Cufflinks - Pin Stripe - Silver - Monogram - Groomsmen Gifts-Default-Silver- On Sale
$ 27.99 $ 33.99
Personalized Cufflinks - Gunmetal - Square - Groomsmen Gifts- On Sale
$ 26.99 $ 32.99
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
Set of 5 Groomsmen Whiskey Decanters - 23 oz. Set of 5 Groomsmen Whiskey Decanters - 23 oz.On Sale
$ 149.99 $ 164.99
Personalized Cufflinks - Silver - Round - Groomsmen Gifts-Default-Silver- On Sale
$ 27.99 $ 32.99
Personalized Kinsale Rectangular 24 oz. Whiskey Decanter - Set of 5 Personalized Kinsale Rectangular 24 oz. Whiskey Decanter - Set of 5Sold Out
$ 149.99 $ 164.99
Personalized Flasks - Personalized Lighters - Set - Groomsmen-Flasks-JDS-2Lines- Personalized Flasks - Personalized Lighters - Set - Groomsmen-Flasks-JDS-2Lines-Sold Out
$ 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
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 Cufflinks - Silver - Oval - Monogram - Groomsmen Gifts- On Sale
$ 27.99 $ 33.99
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 Can Coolers - Black - Stainless Steel - Groomsmen Gifts-Stamped Monogram- Personalized Can Coolers - Black - Stainless Steel - Groomsmen Gifts-Stamped Monogram-Sold Out
$ 20.99 $ 25.99
Personalized Backpack Travel Cooler - 24 Can Capacity Personalized Backpack Travel Cooler - 24 Can CapacityOn Sale
$ 34.99 $ 38.99
Personalized Set of 5 Camouflage Cooler Chair - Sit N Sip Personalized Set of 5 Camouflage Cooler Chair - Sit N SipOn Sale
$ 155.99 $ 189.99
Personalized Growler - Beer - Amber Glass - 64 oz.- Personalized Growler - Beer - Amber Glass - 64 oz.-On Sale
$ 18.99 $ 23.99
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 Sports Weekender Duffel Bag - Set of 5-Blue- Personalized Sports Weekender Duffel Bag - Set of 5-Blue-On Sale
$ 175.99 $ 219.99
Personalized Groomsmen Canvas Shaving Kit-Travel Gifts-JDS- Personalized Groomsmen Canvas Shaving Kit-Travel Gifts-JDS-On Sale
$ 28.99 $ 35.99
Personalized Kinsale Rectangular 24 oz. Whiskey Decanter Personalized Kinsale Rectangular 24 oz. Whiskey DecanterSold Out
$ 37.99 $ 43.99
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 Cufflinks - Set of 5 - Round - Gunmetal - Groomsmen Gifts- On Sale
$ 122.99 $ 153.99
Money Clip & Wallet for Groomsmen-Black- Money Clip & Wallet for Groomsmen-Black-Sold Out
$ 17.99 $ 21.99
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 Cufflinks - Set of 5 - Pinstripe - Groomsmen Gifts-Silver- Personalized Cufflinks - Set of 5 - Pinstripe - Groomsmen Gifts-Silver-Sold Out
$ 135.99 $ 169.99
Set of 5 - Personalized Bullet Lowball Whiskey Glasses Set of 5 - Personalized Bullet Lowball Whiskey GlassesOn Sale
$ 99.99 $ 124.99
Set of 5 Personalized Antique Whiskey Decanters - 24 oz. Set of 5 Personalized Antique Whiskey Decanters - 24 oz.Sold Out
$ 149.99 $ 164.99
Personalized Bullet Lowball Whiskey Glasses - Set of 2 Personalized Bullet Lowball Whiskey Glasses - Set of 2On Sale
$ 39.99 $ 49.99

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.