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Updated Mar 06, 202530 Groomsmen Proposal Gifts for Your Crew
Here are our top picks.
Design: Natalie Romine
Deciding who to include in your wedding party is only half the challenge… you also have to officially invite them to participate in your wedding. Groomsmen proposal gifts are a fun way to ask loved ones to join the party and surprise them with a special treat. Need some help picking out groomsmen gifts for your crew? We've rounded up the best groomsmen proposal ideas, from thoughtful gift boxes to bonus goodies you can give with a card. Read on for our top presents, along with tips on how to ask someone to be a groomsman or best man at your wedding.
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Best Man and Groomsmen Proposal Gifts
Whether you're searching for curated groomsmen proposal boxes or small gifts you can assemble yourself, we've got you covered. Our list is filled with presents to help you pop that all-important question "Will you be my groomsman?" to your buddies. Shop groomsmen proposal gift ideas for everyone from the amateur golfer to the old college roommate, below.
1. Curated Groomsmen Proposal Box
Photo: TheWoodShackGiftCo
Tell your friends to suit up for the role of a lifetime with this pre-filled groomsmen proposal box. It includes goodies like a personalized flask, black sunglasses and dress socks with the simple question of "Will you be my groomsman?" Everything comes elegantly presented in a sleek black box with crinkle paper.
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2. Baseball-Themed Playing Cards
Photo: Uncommon Goods
Wondering how to ask your groomsmen to be in your wedding? Take inspiration from their interests. If they love watching sports, these baseball-themed playing cards will be a home run. Each card features a colorful illustration of an MLB stadium (like Fenway Park and Wrigley Field) for a thoughtful tribute to their favorite pastime. Give them as stand-alone presents, in groomsmen proposal boxes or even as junior groomsmen gifts for younger wedding party members.
3. Custom Golf Balls
Photo: Personalization Mall
Here's a fun idea to ask your groomsmen or best man: invite them out to play golf. Before you head onto the green, take out a set of personalized golf balls for every person. Each trio of Callaway Warbird Plus balls can be printed with their name and wedding titles to nod to your upcoming celebration.
4. Personalized Zippo Lighters
Photo: Zazzle
A personalized zippo lighter isn't just for cigar smokers, you know. These handy gadgets can be used to ignite a campfire, illuminate the darkness or light scented candles at home. They're windproof and stylish, so they'll likely impress the bright sparks in your wedding party. Consider your groomsmen proposal gifts sorted.
5. Old Fashioned Cocktail Cubes
Photo: Uncommon Goods
Planning to make your own groomsmen or best man proposal boxes? Start with these instant cocktail cubes. They're infused with bitters, demerara sugar and fruity extracts and can be used to make Old Fashioned cocktails instantly. And, as they're sold in packs of 24 (eight of each flavor), you can divide them out between your crew. Genius, right?
6. Custom Embroidered Handkerchief
Photo: StickerByOllie | Etsy
Help your groomsmen dress to impress with these custom embroidered handkerchiefs. They can be personalized with any name or a message, like "Will you be my groomsman?" for a thoughtful touch. Your pals can tuck them into their suits for any teary moments that arise during the ceremony.
7. Personalized Multi-Tool
Photo: Leatherman
Our top tip for choosing groomsmen proposal gifts? Pick something related to their genuine interests and personalities. If they're a handy bunch, a personalized multi-tool is a practical gift they'll actually use. Each one hides 10 different implements, including a knife, file, tweezers, scissors and screwdriver. Engrave their name or wedding title on the handle to finish things off.
8. Wooden Valet Trays
Photo: Mark & Graham
Balance practicality with style with this classic groomsmen proposal gift. Made from solid acacia wood, this elegant valet tray will give them a designated spot to keep their valuables safe. Have each one engraved with their monogram for a practical present they'll use long after the wedding day.
9. Movie-Inspired Dress Socks
Photo: shopsockprints | Etsy
If you need groomsmen proposal gifts for a themed wedding, these groomsmen socks are on point. They're inspired by The Lord of the Rings trilogy and feature a punny message that reads "The Fellowship of the Rings" in a nod to your upcoming nuptials. Choose from four colors (black, charcoal, navy and purple) before adding your wedding date and each member's role to the design.
10. Whiskey Glass Set
Shopping for groomsmen or best man proposal gifts on a budget? The Knot Shop has tons of affordable options, like this whiskey glass set. It includes an engravable tumbler and three whiskey stones to keep their drink cool without diluting it. Your guys will look great sipping from these in the get-ready suite.
11. Groomsmen Accessory Set
Photo: The Tie Bar
Another groomsmen invitation idea is to provide something wearable for the big day. This accessory gift set includes a skinny tie and a linen pocket square… perfect for putting the finishing touches to their formalwear. Choose from two shades (sky blue or sage green) for a practical gift your guys can wear again.
12. Wooden Puzzle Box
Photo: Uncommon Goods
Searching for creative ways to ask your groomsmen to be in your wedding? This wooden puzzle box will add some mystery to your proposal. Simply place a prize (like a handwritten card or gift voucher) in the front slot, then lock the box before handing it over. The recipient will have to figure out the correct sequence to open it and retrieve their reward at the end. Clever, we know.
13. Personalized Cooler Backpack
Photo: JuneSummerShop | Etsy
If your crew is outdoorsy, these cooler backpacks make excellent groomsmen proposal gifts. Made from waterproof materials, they're perfect for camping, hiking and exploring outside. The sturdy handle and adjustable strap is easy to carry, while the insulated lining keeps food and drink fresh for hours. Hide their favorite snacks inside for a thoughtful surprise.
14. Sleek Cigar Cases
Photo: Personalization Mall
These groomsmen proposal gifts look like something out of Mad Men. Inspired by the past, these cigar cases are made from polished stainless steel and can be etched with any name or title. Each one comes with a cutter to trim cigar ends before lighting up. Fill them with cigars before handing them out to your guys.
15. Craft Beer Selection
Photo: Craft Beer Club
If your friends like beer, they'll definitely say "yes" to these craft brews. The box is stocked with everything from IPAs to sours, all made in breweries across the United States. Choose from three different quantities (six, nine or twelve cans) and add a gift message at the checkout to be sent via email. "Will you beer my best man?" or "Brew are the best" are fun ideas to ask your groomsmen.
16. Funny Personalized Mug
Photo: Uncommon Goods
Alcohol-related gifts may be popular, but they're not the only way to ask someone to be your best man or groomsman. For a booze-free alternative, consider these personalized coffee mugs. They're decorated with playful illustrations resembling your crew, with space to add their names or wedding party titles underneath. Play around with customization options (like outfits, hairstyles and accessories) to tailor the design to each recipient.
17. Customized Bottle of Wine
Photo: Mano's Wine
It's totally fine to get a best man proposal gift that's different from the rest of your crew. Make sure he feels like number one with this customized bottle of wine. The inside holds a full-bodied cabernet sauvignon, while the outside can be etched with his name, title or a custom design. Even when the wine is gone, he can hold onto the bottle as a memorable keepsake.
18. Poker Game Set
Photo: Brass Monkey
We couldn't write a list of groomsmen and best man proposal ideas without including something fun. If your guys enjoy playing games, they'll go all in for these poker gift sets. Each box includes 100 poker chips and a deck of playing cards—and better yet—a set of instructions so even novices can join in.
19. College-Inspired Pouches
Photo: Uncommon Goods
Here's a groomsmen proposal idea for the former college roomies: A woven pouch inspired by the university you attended. Whether you and your pals met at Boston College, the University of Florida or Virginia Tech, these colorful accessories will bring back memories. Stash candies inside or add them to a gift box with other small presents.
20. Groomsmen Shot Glasses
Photo: Amazon
If your friends like to party, this groomsmen proposal gift will get them in a celebratory mood. This set of five shot glasses are all decorated with black tuxedos so even the drinkware is dressed for the occasion. It includes one glass for the groom, one for the best man and three for the groomsmen. Expect these to emerge at the bachelor party.
21. Engraved Cuff Links Set
Cuff links are another classic gift for asking your groomsmen to be there for you. These ones come in silver or gold, with a matching tie bar and money clip in a personalized wooden box. Have them engraved with each person's initials or name for a practical (and personal) gift they can wear to the wedding.
22. Beard Grooming Kit
Photo: WhiteNaturalsStore | Etsy
Personalized presents aren't the only option when you're shopping for groomsmen proposal gifts. This set of grooming products is ideal for the bearded members of your wedding party. It includes a pair of stainless steel scissors, a beard-shaping tool, a brush, a comb, soothing balm and nourishing oil to help tame facial hair.
23. Insulated Tumblers
Photo: Amazon
Sometimes, the best groomsmen proposal gifts are the most useful, especially when the big day rolls around. Make sure they're sufficiently hydrated with these insulated tumblers. They're made from stainless steel and can keep drinks hot for up to five hours or cool for nine hours. Best of all, they come in a six-piece set: one "Groom," one "Best Man" and four "Groomsman" designs.
24. Personalized Watch Box
Photo: Personalization Mall
This personalized watch box is an excellent groomsman or best man proposal idea that'll be useful beyond the wedding. It's made from faux leather and glass that can be engraved with any wedding party title, name, message and date. The inside is lined with felt to keep their treasured pieces polished and scratch-free.
25. Music-Inspired Coasters
Photo: Uncommon Goods
Here's a winning gift idea for the music lovers in your crew. These retro coasters are made from upcycled records, with each one representing a different album or music genre. They're sold in sets of six, so you'll (probably) have enough to go around for each person. Team them with mugs, coffee beans or another accessory for a groomsmen proposal box that'll top the charts.
26. Custom Leather Belt
Photo: MankitLeather | Etsy
If you think a belt can't be a cool groomsmen proposal gift, think again. This leather accessory has a secret feature that sets it apart from the rest. The outside can be personalized with their initials, while the inside has space for a special message (think: "Will you be my best man?" or something similar.) Snag them in six colors (brown, tan, black, blue, gray or green) for each wedding party member.
27. Engraved Whiskey Glasses
Photo: Personalization Mall
Still wondering how to ask your groomsmen to be in your wedding? Invite them over for a nightcap and propose to them with these engraved whiskey glasses. Each one can be etched with their name, wedding title or nickname for a thoughtful keepsake they'll treasure for years to come.
28. Personalized Tape Measure
Photo: whiskeynweddingbells
While a tape measure might sound like an unusual groomsmen proposal idea, it's a surprisingly practical (and sweet) gift they won't see coming. This handy tool can be engraved with their names and a personalized message that reads: "A man is measured by the quality of his friends." We can't think of a more heartfelt way to ask your guys to be there when you say, "I do."
29. Leather Charger Roll-Up
Photo: Swanky Badger
We'll never tire of suggesting practical groomsmen proposal gifts. This leather roll-up will help your tech-loving pals stay organized while packing for your wedding. It has compartments for phone chargers, cables and earbuds… so they (probably) won't forget to bring their essentials with them. Add their name or initials for a practical present they can take on future trips.
30. Embroidered Hoodie
Photo: Zazzle
Cozy loungewear is popular for bridesmaids, but why should guys miss out on the fun? This embroidered hoodie is a nice way to ask your pals to be your groomsmen plus they can wear it on the morning of (or morning after) the wedding. It's made from a soft cotton blend and is stitched with the word "groomsman" on the front. Order these early so they can wear them to the bachelor party.
Best Man and Groomsmen Proposal FAQ
If you need advice on how to plan your best man and groomsmen proposals, we can help simplify the process. Whether you're asking close friends, family members or old college roomies, use the FAQs and tips below to guide you.
What is a best man or groomsman proposal?
A best man or groomsman proposal is a way of asking your closest friends to be part of your wedding party. It's a thoughtful approach that can make the moment feel official and is often accompanied by a personal gift. From grand gestures to heartfelt keepsakes, there are numerous ways to ask someone to be a groomsman or best man.
Do you have to propose to your guys with gifts?
While groomsmen proposal gifts are not required, they're a nice touch that can make your crew feel appreciated. Even a small and thoughtful gift can go a long way, especially when paired with a groomsmen proposal card or a handwritten note. Practical presents are also popular and can include something they'll need for the wedding day, like personalized accessories or small clothing items.
How should you give them their presents?
You can give your best man and groomsmen their presents both in person or by mail—whatever is most convenient for everyone involved. If they live nearby, you could arrange to hang out together before handing over your gifts. Or, if your friends live out of state, sending a thoughtful groomsmen proposal gift in the mail might be better. Wondering when to give your groomsmen their gifts? The best time to give a groomsman proposal gift is when you ask them to join your wedding party (ideally before sending your save-the-date cards or at least six months before the wedding.) That way, they'll have plenty of advance notice to plan their schedule and get excited about the celebration.
