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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
$ 155.90 $ 182.99
Set of 5 Groomsmen Whiskey Decanters - 23 oz. Set of 5 Groomsmen Whiskey Decanters - 23 oz.On Sale
$ 159.99 $ 164.99
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 Whiskey Decanter - 23 oz. Personalized Whiskey Decanter - 23 oz.On Sale
$ 37.99 $ 43.99
Groomsmen 12-Pack Trail Cooler With Built-In Bottle Opener Groomsmen 12-Pack Trail Cooler With Built-In Bottle OpenerOn Sale
$ 35.99 $ 43.99
Personalized Bamboo Flask Set Personalized Bamboo Flask SetOn Sale
$ 26.99 $ 33.99
Personalized Whiskey Decanter Set with 2 Lowball Glasses Personalized Whiskey Decanter Set with 2 Lowball GlassesOn Sale
$ 52.99 $ 64.99
Personalized Set of 5 Groomsmen Cooler Chairs Personalized Set of 5 Groomsmen Cooler ChairsOn Sale
$ 189.99 $ 249.99
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 Sit N Sip Cooler Groomsmen Gift Personalized Sit N Sip Cooler Groomsmen GiftOn Sale
$ 39.99 $ 49.99
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 Flasks - Cigar Case - Combo - Stainless Steel - Groomsmen-Default- On Sale
$ 25.99 $ 31.99
Personalized Trappers Supply Heavy Canvas Duffel Bag Personalized Trappers Supply Heavy Canvas Duffel BagOn Sale
$ 52.99 $ 59.99
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 - Gym Bag-Travel Gifts-JDS-Black- Personalized Groomsmen Duffel Bag - Gym Bag-Travel Gifts-JDS-Black-On Sale
$ 47.99 $ 50.99
Engraved Harmonica Stainless Steel Hohner Harmonica-Executive Gifts-JDS-Default- Engraved Harmonica Stainless Steel Hohner Harmonica-Executive Gifts-JDS-Default-On Sale
$ 18.99 $ 23.99
Personalized Black 20 oz. Travel Tumbler Personalized Black 20 oz. Travel TumblerOn Sale
$ 24.99 $ 30.99
Personalized Bullet Lowball Whiskey Glass Personalized Bullet Lowball Whiskey Glass
$ 24.99
Personalized Can Coolers - Leather - Black - Groomsmen Gifts-Default- On Sale
$ 23.99 $ 29.99
Personalized Golf Shoe Bag - Embroidered-Sports Gifts-JDS- Personalized Golf Shoe Bag - Embroidered-Sports Gifts-JDS-On Sale
$ 32.99 $ 35.99
Personalized Antique 24 oz. Whiskey Decanter Personalized Antique 24 oz. Whiskey DecanterOn Sale
$ 37.99 $ 43.99
Personalized Cufflinks - Gunmetal - Round - Groomsmen Gifts-Cufflinks-JDS- On Sale
$ 28.99 $ 32.99
Personalized Men's Canvas Weekender Duffel Bag Personalized Men's Canvas Weekender Duffel BagOn Sale
$ 52.99 $ 59.99
Personalized Black Weekender Duffel Bags for Groomsmen - Set of 5-Travel Gifts-JDS- Personalized Black Weekender Duffel Bags for Groomsmen - Set of 5-Travel Gifts-JDS-On Sale
$ 175.99 $ 219.99
Money Clip & Wallet for Groomsmen-Black- Money Clip & Wallet for Groomsmen-Black-
$ 21.99
Personalized 30 oz. Decanter Personalized 30 oz. DecanterOn Sale
$ 39.99 $ 43.99
Personalized Wood Watches for Groomsmen Personalized Wood Watches for Groomsmen
$ 57.98
Personalized Cufflinks - Brass - High Polish - Groomsmen Gifts-Default-Brass- On Sale
$ 28.99 $ 33.99
Personalized Cufflinks - Round - Classic - Groomsmen Gifts-Silver- On Sale
$ 28.99 $ 30.99
Personalized Cufflinks - Set of 5 - Round - Gunmetal - Groomsmen Gifts- On Sale
$ 122.99 $ 153.99
Personalized Sports Weekender Duffel Bag - Set of 5-Blue- Personalized Sports Weekender Duffel Bag - Set of 5-Blue-On Sale
$ 175.99 $ 219.99
Magnetic Money Clip-Rustic- Magnetic Money Clip-Rustic-
$ 21.99
Set of 5 Wedding Personalized Bullet Lowball Whiskey Glasses Set of 5 Wedding Personalized Bullet Lowball Whiskey GlassesOn Sale
$ 120.99 $ 124.99
Personalized Drink Carrier  - Royal Blue Personalized Drink Carrier  - Royal BlueOn Sale
$ 24.99 $ 30.99
Set of 5 Groomsmen Personalized Antique Whiskey Decanters - Set of 5 Groomsmen Personalized Antique Whiskey Decanters -On Sale
$ 175.99 $ 189.99
Personalized Cufflinks - Silver - Modern - Square - Groomsmen Gifts-Silver- On Sale
$ 28.99 $ 30.99
Personalized Lowball Whiskey Glasses - Mongrammed Whiskey Glasses for Groomsmen - Set of 4-SingleInitial- Personalized Lowball Whiskey Glasses - Mongrammed Whiskey Glasses for Groomsmen - Set of 4-SingleInitial-On Sale
$ 34.99 $ 49.99
8 oz. Personalized Whiskey Lowball Glass with Golf Ball 8 oz. Personalized Whiskey Lowball Glass with Golf BallOn Sale
$ 30.99 $ 32.99
Personalized Flasks - Cigar Case - Lighter - Combo - Groomsmen - 1.5 oz.- On Sale
$ 42.99 $ 53.99
Engraved Groomsmen Pocket Watch-Executive Gifts-JDS- Engraved Groomsmen Pocket Watch-Executive Gifts-JDS-On Sale
$ 33.99 $ 41.99
Personalized 15 oz Black Travel Tumbler Personalized 15 oz Black Travel TumblerOn Sale
$ 25.99 $ 32.99
Men’s Waxed Canvas Travel Bag for Groomsmen - Field Tan-Travel Gifts-JDS-RoseGold- Men’s Waxed Canvas Travel Bag for Groomsmen - Field Tan-Travel Gifts-JDS-RoseGold-On Sale
$ 61.99 $ 76.99
Personalized Cufflinks - Pin Stripe - Silver - Monogram - Groomsmen Gifts-Default-Silver- On Sale
$ 28.99 $ 33.99
Personalized Cufflinks - Silver - Round - Groomsmen Gifts-Default-Silver- On Sale
$ 28.99 $ 32.99
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
$ 179.99 $ 208.99
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
$ 199.99 $ 229.99
Personalized Bamboo Tumbler Personalized Bamboo TumblerOn Sale
$ 22.99 $ 28.99

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.