The 30 Best Groomsmen Proposal Gifts for Asking the Guys

Here's how to pop the *other* question.
Groomsman proposal gift ideas
Photos, from clockwise: Paravel, Amazon, Uncommon Goods, Swanky Badger
emily rumsey the knot editor
Emily Rumsey
emily rumsey the knot editor
Emily Rumsey
Assistant Commerce Updates Editor
  • Emily helps maintain and update e-commerce content for The Knot
  • Before joining The Knot Worldwide, Emily worked as a website editor and manager for The Paleo Diet®
  • Emily holds two bachelor's degrees in Journalism and International Affairs with a Chinese minor
Updated Dec 05, 2023
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Deciding who you want to include in your wedding party is only half the challenge—you also have to let them know they're officially invited to your big day! A best man or groomsmen proposal is a fun way to ask your friends to be by your side and an excuse to treat them to special gifts that honor the occasion. Searching for great groomsmen gifts for your crew? We're here to help make asking your guys a unique and memorable experience. From thoughtful gift boxes to bonus goodies you can give with a card, these groomsmen proposal ideas are sure to win them over.

In this article:

Best Man and Groomsmen Proposal Gifts

Looking for a gift to help you pop that all-important question, "Will you be my groomsman?" You've come to the right place. Whether you're searching for standalone best man proposal gifts or want to curate your own groomsmen proposal boxes, these presents have you covered. We've found options for everyone, from the golfer to the amateur mixologist to the old college roommate and beyond. Below, you'll find 30 thoughtful groomsmen proposal gift ideas and memorable keepsakes for this unique moment in your wedding journey.

1. Custom Golf Balls

Personalized golf balls for your groomsmen
Photo: Personalization Mall

If you're wondering how to ask the guys to be your groomsmen, here's a fun way to get their attention. Invite them out for a round of golf and whip out a box of personalized golf balls for each person. These Callaway Warbird Plus balls come in a set of three printed with the name and wedding title of your choice. Now, they'll be reminded of you (and your upcoming wedding) every time they tee off.

2. Stylish Groomsmen Proposal Boxes

Stylish Groomsmen Proposal Boxes
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 label "Will you be my groomsman?" printed on the front. Best of all, everything comes in a sleek black box with crinkle paper for a thoughtful presentation.

3. Monogrammed Handkerchiefs

Personalized handkerchief groomsmen proposal gift
Photo: Mark & Graham

Make sure your groomsmen are dressed to the nines by gifting them a linen handkerchief embroidered with their initials. Equal parts practical and stylish, it's easily one of the best ideas for asking your groomsmen to be there for you. They can even tuck it into their suit pocket for support during one of life's most emotional occasions—the wedding.

4. Cocktail Groomsmen Proposal Boxes

Cocktail making kit groomsmen proposal box idea
Photo: Shaker & Spoon

When it comes to picking wedding party gifts, alcohol is a classic choice that never goes out of fashion. Pair a bottle of bourbon with a gift box from Shaker & Spoon to take your groomsmen proposal to the next level. The kit includes winter spice syrup, orange bitters, oil spray and black cherries so they can craft their very own Old Fashioned right at home. Bonus: The box makes up to four drinks, so you can look forward to toasting your engagement together.

5. Sleek Cigar Cases

Engraved cigar case and monogrammed cutter groomsmen proposal gift idea
Photo: Personalization Mall

If you're looking for creative ways to ask your groomsmen to stand by your side, let the past inspire you. For decades, gentlemen have been gathering to smoke cigars and enjoy one another's company. Invite your crew to do just that, then give each of them their own engraved cigar case and cutter. These personalized gifts will get you on their good side before the wedding planning assistance gets serious.

6. Custom Dress Socks

Patterned dress socks with personalized labels groomsmen proposal gift idea
Photo: NoColdFeetCo

Ensure they don't get cold feet with these funky groomsmen socks. Each pair comes with a personalized label that asks, "Will you stand with me as my groomsman?" Choose from a mix of colors and prints for a wearable gift they can rock on the wedding day. Bonus points for the affordable price tag.

7. Pop Culture Tie Bars

Pop Culture Tie Bars for the best groomsmen gift

If you're looking for a unique standalone gift to ask your groomsmen to be part of your big day, draw inspiration from their favorite movie franchise: Star Wars. This tie bar is designed to look like the hyperdrive outer space scenes from the movie—and it even glows in the dark. It's a fun way for them to add a touch of personality to their formalwear and is especially fitting if you're planning a themed wedding.

clock cuff links for the best groomsmen's gifts
Photo: Amazon

Don't be afraid to have some fun when choosing your best man or groomsmen proposal gifts. If your buds have a habit of being late, these working clock cuff links are a playful (and stylish) way to remind them to show up on time. Even better, they're made from polished rhodium-plated brass and come in a very giftable box, so you can skip the gift-wrapping altogether.

9. Trendy Travel Tumblers

travel drinks tumbler for your groomsmen
Photo: Stanley

A Stanley cup is always a winning gift idea, whether it's for your best man, groomsmen or another member of your wedding party. It features a lid with a rotating cover that can be adapted in three ways (with a straw, a wide mouth or a full-cover top) and can keep drinks hot or cold for hours on end. Choose from a range of colors, sizes and customization options to fit your pals' personalities and tastes.

10. Wooden Valet Trays

wooden valet trays for the best groomsmen gift
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 special spot to keep accessories (like a wallet or keys) safe when they're not using them. Have each one engraved with their monogram for a personal piece of home decor they'll be proud to show off.

11. Luxe Grooming Products

Rituals grooming set for the best gifts for groomsmen
Photo: Carethy

If you don't want to go down the personalized route, there are tons of other groomsmen proposal gifts to consider instead. A set of luxurious grooming products is a gift any guy will appreciate, especially when it smells as good as this one from Rituals. It comes with a foaming shower gel, hydrating body lotion, a two-in-one shampoo and a travel-sized bottle of cologne infused with a spicy patchouli and cedarwood scent. It's sure to leave them feeling fresh and pampered ahead of the big day.

12. Funny Best Man Notebook

funny notebook gift for your groomsmen
Photo: Zazzle

There are no hard and fast rules on how to ask someone to be your best man. If you two have a goofy relationship, this funny best man proposal gift is sure to get the laughs in. The spiral-bound notebook features their initials and text that reads "Best Man Speech Notes and Jokes." Write a silly (or sweet) message inside, along with a few tips to help them get into speech-writing mode.

13. Monogrammed Packing Cubes

Personalized Monogrammed Packing Cubes
Photo: Paravel

Whether you're planning a destination wedding or just want to get your groomsmen practical gifts, a set of packing cubes is an excellent idea. These four flexible boxes are made from lightweight, water-resistant materials and feature zip enclosures to keep contents safe—but that's not all. Each one is made from recycled plastic bottles and folds completely flat for easy storage. Have them personalized with custom embroidery so they won't have to worry about their stuff getting mixed up.

14. Engraved Whiskey Glasses

Personalized 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 up to three lines of personalized text, like their name, wedding title or nickname for a thoughtful keepsake they'll treasure for years to come.

15. Personalized Multi-Tool

mutitool gift for your groomsmen
Photo: Leatherman

If we could give one piece of advice for picking out groomsmen proposal gifts, it's this: Choose something that suits their genuine interests and personalities. If they're a pretty 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—so they can up their DIY game with minimal effort.

16. Insulated Coffee Mug

Insulated Coffee Mug gift for your groomsmen
Photo: Hydro Flask

While alcohol-related gifts are a popular choice, we get that they're not for everyone. If you're looking for a booze-free alternative, consider one of these insulated mugs from Hydro Flask. They're made from pro-grade stainless steel that keeps drinks hot or cold for hours and have splash-resistant lids to minimize spillages. Choose from a variety of trendy shades (like berry red or indigo blue) and pair it with their favorite coffee beans for a thoughtful touch.

17. Music-Inspired Coasters

Music-Inspired Coasters gift for your groomsmen
Photo: Uncommon Goods

Here's a winning gift idea for the music-loving members of your wedding party. These retro coasters are made from upcycled records, with each one in the six-piece set representing a different album or musical genre. Team them with their favorite bottle of whiskey, coffee or other accessory for a groomsmen proposal box that really rocks.

18. Groomsmen Shot Glasses

Groomsmen Shot Glasses for the best wedding party gift
Photo: Amazon

You're tying the knot, so it's time to take a shot! This set of five wedding party glasses (one "Groom," one "Best Man" and three "Groomsman") are all decorated with black tuxedos so even the drinkware is dressed for a formal occasion. They make a great groomsmen invitation gift that you'll definitely see again at the bachelor party.

19. Funny Personalized Mug

Customized portrait coffee mug gift
Photo: Uncommon Goods

This personalized mug is easily one of our favorite groomsmen or best man proposal ideas. It features a playful illustration of their likeness created using different design options, like outfits, hairstyles and accessories. Each one also includes space for custom text that you can alter to display the names and titles of each wedding party member. Invite them over for a coffee or send them their gifts in the mail for a fun surprise.

20. LEGO Car Set

LEGO set for the best groomsmen's gifts
Photo: Amazon

Just because you're getting married doesn't mean you have to be all grown up with your groomsmen proposal gifts. LEGO sets are a creative way to ask your guys to join your wedding party and set the tone for all the exciting moments to come. This mini replica of an Aston Martin car is sure to impress motor enthusiasts and James Bond fans alike and will score you brownie points with your fun-loving crew.

21. Personalized Zippo Lighters

Customized Zippo lighters for the best groomsman's gift
Photo: Zazzle

A personalized zippo lighter isn't just for cigar smokers, you know. These ultra-stylish gadgets can be useful in any number of situations, from igniting a campfire to creating a relaxing mood at home with scented candles. They're durable, windproof and practical (not to mention stylish) and are guaranteed to impress the bright sparks in your wedding party. Consider your "Will you be my groomsman?" gifts sorted.

22. Funky Dopp Kit

Cool dopp kit gift for your groomsmen
Photo: Nordstrom

Sometimes, the best groomsmen proposal gifts are the most useful—especially when the big day rolls around. Make sure they're prepped for the getting-ready suite with these cool dopp kits. They're made from recycled polyester, have a waterproof zip to keep the contents secure and come in two funky shades: bright yellow and steel blue. If you want to go the extra mile, pick up a few travel-sized grooming essentials to tuck inside.

23. Best Man Fishing Lures

Groomsmen fishing lure best man proposal gift idea
Photo: BelovedBySMDesigns

Take inspiration from his hobbies with your best man proposal gift. You can use this engraved fish hook on your next trip to the lake together. Or, for an extra-thoughtful proposal idea, invite him to go fishing and hand over your gift while you're setting up the rig. It'll be a nice opportunity to properly let him know why you want him to be a VIP on the big day.

24. Baseball-Themed Playing Cards

baseball playing cards for your groomsmen's gift
Photo: Uncommon Goods

Deciding how to ask your best man and groomsmen to be part of your special day can be as simple or extravagant as you want it to be. If your guys love nothing more than chilling out and watching sports, these baseball-themed playing cards will be a home run. Each card in the deck features a colorful illustration of a Major League Baseball stadium—like Fenway Park and Wrigley Field—and is sure to make poker night feel extra special. Gift these as stand-alone presents or as part of a groomsmen proposal box, depending on your budget.

25. Custom Guitar Picks

personalized guitar pick groomsman gift
Photo: Tomzasa

If you and your crew were part of a band in high school, this groomsmen proposal gift idea will take you back to the good old days. These wooden guitar picks can be customized to include your guys' names and their wedding party roles for a thoughtful touch. You can also choose an engraved box for each for a more polished presentation.

26. Engraved Wooden Watches

engraved personalized wooden wrist watches
Photo: Swanky Badger

Watches make for an excellent groomsman gift idea, as they're both practical and keepsake-worthy. Your crew can wear these personalized timepieces for your wedding and beyond. Each one is crafted from sandalwood and engraved with their wedding title, monogram and the date of your special day on the back.

27. Novelty Tuxedo Hoodie

Funny hoodie for your groomsmen's gift
Photo: Amazon

Searching for a goofy gift to ask them: "Will you be my groomsman?" Look no further than this novelty hoodie designed to look like the front of a tuxedo. Sure, it's a little cheesy, but it's bound to make your pals laugh when they unwrap theirs. Choose from a variety of colors (including black, burgundy and royal blue) for a cozy gift they can wear the morning of the wedding.

28. College-Inspired Pouches

university themed pouches for your groomsmen's gifts
Photo: Uncommon Goods

Here's a winning 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 Pennsylvania or North Carolina State, these colorful accessories will bring on plenty of nostalgia. Fill them with candies or include them in a bigger box for a groomsman or best man proposal gift that's practical and sentimental.

29. Best Man Skateboard

best man skateboard gift for your groomsman
Photo: Zazzle

It's totally fine if you want to get your best man a gift that's different from the rest of your wedding party. Make sure he feels like number one with this custom skateboard from Zazzle. It's made from premium maple wood and features his wedding title on the front in a retro-style font. Gift it to him as a fun follow-up to your groomsmen invitation for a sweet way to ask, "Will you be my best man?"

30. Personalized Tape Measure

personalized tape measure gift for your groomsmen
Photo: whiskeynweddingbells

Taking a more unique approach can really pay off, so feel free to get creative with your gifting choices. While a tape measure might sound like an unusual pick, it's a surprisingly practical (and sweet) groomsmen proposal 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." Aww!

Best Man and Groomsmen Proposal FAQ

If you need some advice on how to plan your best man and groomsmen proposals, we're here to help simplify the process. Whether you're asking close friends, family members or old college roomies, you can use the FAQs and handy tips below to guide you.

What is a best man or groomsman proposal?

Simply put, 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 so many 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 extra special. 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 a good idea and can include something they'll need for the wedding day, like personalized accessories or small clothing items such as socks.

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 you and your crew. If they live nearby, getting them together for an impromptu hang could be the way to go. On the other hand, if your friends live out of state, sending a thoughtful groomsmen proposal gift to their door may be the best option. Wondering when to give your groomsmen their gifts? The best time to hand over 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, you can give them plenty of advance notice to plan their schedule (and get excited about the big day, of course!).

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