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This post was originally published on August 4, 2020 and gets updated periodically to remove outdated links and grow this list with new items! I’ll be reviewing this post, adding new products, and cleaning up any broken links that don’t work anymore; with its most recent update being its current publishing date. Follow me on Facebook to keep informed on when this and other Roundup Posts get updated!
With our Bridesmaids all taken care of with 50 Bridesmaid Proposals Under $15, I had to make a corresponding Groomsman Proposal Post so that the groomsmen are appreciated and invited to your wedding party just like your girls! From fun personalized glassware, to cards or cigars, I’ve compiled a variety of fun and unique Groomsmen Proposals that they will love, with all of them being under $15!
2. Personalized Groomsman Whiskey Glasses
For those whiskey connoisseurs out there, these personalized low ball glasses are the perfect groomsman proposal! Similarly to the beer mugs, these glasses come in a variety of design options to suit your taste.
For the coffee loving campers out there, these stainless steel groomsmen mugs are perfect for your weekend groomsmen proposal in the woods! These mugs come in black or silver with the common wedding roles of groomsman, best man, and usher.
4. Etched Initial Pint Glasses
If pint glasses are more your style than beer mugs, these personalized initial pint glasses are a great choice to pair with your favorite craft beer to propose to your groomsmen, and I love the greenery design!
5. Personalized Groomsman Proposal Boxes
This box is the perfect packaging to invite your groomsmen with a bottle of their favorite scotch, whiskey, or other spirits! These black boxes come with 4 different lettering color options: gold, silver, rose gold, and white.
6. Customized Shoebox Gift Box
For a groomsmen proposal box for the shoe collectors in your group, these customized shoe boxes are the unique package that they’ll adore! These shoe boxes come in a variety of popular brand label designs, with the couples’ names, wedding date, wedding party roles, and label color.
7. Groomsmen Socks with Proposal Boxes
I love proposals that give your boys something to wear on your special day, so I couldn’t say no to these cute socks! These modern black groomsman socks are personalized with white lettering with the recipient's wedding title and a personalized label on the box so they are ready to gift immediately! The gift boxes can be personalized not only as groomsman proposals, but also as thank you gifts, father of the bride gifts, or groom gifts.
8. Groomsmen Socks with a Personalized Proposal Tags
For a variety of sock color and pattern options, these socks are a perfect choice! While they don’t come in a box, they still come with an adorable personalized tag to invite your groomsmen to your wedding party.
9. Groomsman Proposal Bottle Carrier
For your craft brew loving groom A fun and easy groomsman proposal are these personalized 6 Pack holders! They can be personalized with each groomsman’s name as well as each man’s role in your wedding, just add a sampling of your groom’s favorite drinks!
For the bearded boys in the group, a classy and useful proposal like these gorgeous engraved beard combs are sure to be appreciated! Each of these combs is engraved with one of eight designs, along with either your groomsmens' names or any custom text you desire.
11. Personalized Razors
To complement the beard combs for your clean shaven fellows, these personalized razors are a lovely option! These razors are engraved with the names of your recipients, in one of several font styles.
For a classy and customizable bottle opener, look no further than these beauties! They can be personalized with one of several designs, or completely customized with a design of your own!
13. Suit Up Groomsman Proposal Bottle Openers
These bottle openers are perfect for proposing to your groomsman at a barbeque; you give it to your groomsmen to open their beer, and the proposal is etched into the faux leather wrap! Available in 4 color options, each bottle opener is further personalized with your wedding party’s names and wedding roles for a fun personalized proposal.
14. Chug To Accept Groomsman Proposal Koozies
These whimsical arrow decal koozies are a fun way to propose to any bridal party who loves to share a drink together. Coming in 20 different colors and many wedding role choices, these koozies feature the wedding role on the front, with “chug to accept” playfully decorating the back, perfect for gifting with a soda or favorite beer for your friends to accept their roles!
15. Groomsman Proposal Whiskey Label
As a crown royal fan myself, I had to include these whiskey labels on the groomsman proposal list! Each label is personalized with your wedding party member’s name and wedding role, along with your names and wedding day, along with the color of the bow tie on the label.
16. Groomsman Proposal Puzzles
If you want a cute Puzzle to go with the Bridesmaid Proposal Puzzles from our 50 Bridesmaid Proposals Under $15, then these puzzles are the perfect pairing for your Groomsmen! The puzzle can be personalized with your recipient’s name and wedding title, arriving in a cute little pillow box available in a variety of colors.
I love man card themed proposals because of a running joke between my own husband and his groomsmen, so I had to include these proposal cards! These hilarious cards come with codes for several situations, from groomsmen, to fathers to even husbands, so your whole party can be entertained and invited, all personally endorsed by you on the back!
18. Personalized Engraved Stainless Tumblers
For keeping their drinks hot or cold, these personalized engraved stainless tumblers are a classy gift they’ll use again and again! These tumblers come in several colors, with the first initial and name engraved for each guy.
19. Laser Engraved Matte Black Groomsmen Flasks
For a more modern flask choice, these matte black laser engraved flasks are a great option! Available in 9 different design options, each flask can be personalized with your groomsmen’s initials, name, or both!
20. Bow Tie Groomsman Proposal Card
These classy and sassy bow tie cards are a great way to invite out of town groomsmen! Each card is personalized with your groomsmen’s name and wedding role, printed on white card stock complete in a white envelope.
Another fun lighter option for your groomsmen are these lighters, pretty and personalized with your groomsmen’s initials! Each lighter can be personalized with up to three lines of text and is packaged in a small black box for easy gifting!
This Groomsmen definition card is a perfect fit for a classy card with an amusing proposal style! Under the guise of a dictionary definition, it gives all the fun and entertaining responsibilities you expect from your supporting men, all while keeping it a classy looking card for an upscale event! Looking for custom definitions? You can change the text to whatever you like and still keep your cards under $5!
23. Groomsman Initial Shot Glass Proposal Box
These initial shot glasses come with a proposal box in tow, perfect for inviting you groomsmen with a shot to tie the knot! Each box can be personalized for either groomsmen or your best man and comes with a personalized initial shot glass in pretty paper packaging!
24. Personalized Hunting Knife
For those outdoorsy grooms and their boys, these personalized hunting knives would be the perfect way to invite them to your wedding party, maybe on a camping trip! These knives can be engraved on either the front or back handle, with engraving on both available for a little over $15!
Another perfect outdoorsy summer proposal gift are these engraved sunglasses! They are available in 3 different lens shades and each earpiece is personalizable, so you can put their initials on one side and their wedding role on the other!
If, like me, your groomsmen are better off caffeinated, these hilarious mugs are the perfect choice! They are great as work mugs or home mugs, and let’s be honest, the bride is the one who makes the groom send these.
Another great mug themed groomsmen proposal choice are these classic campfire mugs! They come in five different colors and can be personalized with over a dozen lettering color choices, including gold, rose gold and many other color options!
The classy koozie to propose to your wedding party with must be these engraved can coolers! Available in three colors, these koozies are engraved with your groomsmen’s initials and first or last names for a classic design perfect for proposals or bachelor party favors.
29. Scratch Off Groomsman Proposal Card
For a fun lottery themed proposal card, look no further than this super cute scratch off proposal card! These scratch off cards come themed for groomsman, best men, and ushers based on the wedding themed icons, complete with an adorable little legend on the back to let your guys know what wedding role they won!
30. Mini Pokeball Wish Jar Proposal Box
I’m a super pokefan so if you groom is too, these adorable little pokejars are the perfect keepsake to invite his fellow trainers with! These cute little bottles feature suspended pokeballs with a proposal tag personalized for groomsmen, best man, or ushers, a fun and unique proposal for your man to catch his best men for his wedding team!
31. Groomsmen Hot Sauce Bottles
For a fun and unique proposal gift, these Groomsmen Hot Sauce bottles are adorable, creative, and delicious! The labels are available in one of two styles in a variety of wedding party roles, so you can pick your favorite and order bottles for your whole group of spice loving friends.
For other fun and unique, and hobby themed proposals, Check out this Groomsmen Proposal Post!
32. Star Wars Groomsman Proposal Print
For those nerdy grooms and their men, these star wars groomsman proposal prints are a perfect pick! This digital file downloads instantly and can then be easily printed at home or your local print shop, then you can frame them or gift them as is!
33. Tie Bar Groomsman Proposal
For a classy winter or mountain wedding proposal, these tie clips are a wonderful option! The tie clips come in an adorable gift box, complete with a personalized card inside to invite you best men to your bridal party.
I love these Personalized Pocket Watches for their vintage and steampunk vibes, I’ll while being an affordable proposal for your best guys! These watches come in matte black or gunmetal, with engraving available on the front back, and inside the lid of the pocket watch.
35. Modern Tuxedo Proposal Card
For a modern black tie wedding, these groomsmen proposal cards hit just the right note. Each card is personalized with the future bride’s new last name, as well as the wedding role you are inviting your guy to be.
These modern and minimalist tie clips are a perfect proposal your groomsmen can also sport as an accessory on your big day! These tie clips come in three finishes and three sizes, along with your wedding party’s initials being stamped on them, as a personal touch for each man.
37. Polka Dot Groomsman Socks with Personalized Kraft Tags
Another adorable groomsmen sock proposal are these dapper dotted socks! In addition to dots, these adorable sock and tag combos actually come in dozens of fun prints and colors so make sure to check out all their amazing options before deciding on the perfect choice for your best men!
38. Initial Cufflinks and Tie Clips
To give you guys some swag for the big day, these initial cufflinks or tie clips are a modern and elegant proposal option! Pick either a set of cufflinks or black tie clip, then have them all personally engraved with the text or date of your choice.
39. Personalized Tuxedo Gift Boxes
Need a unique box to dress up some DIY proposal pieces? These tuxedo boxes are the perfect packaging! Each box and bow ties come in a variety of color combinations to personalize to your party, along with each box being customized with your recipient’s name, title, or both.
For a little box that makes a big statement, these 3D Groomsmen Proposal boxes are a beautiful option, all while also being able to house your own DIY Cufflinks if you like! These boxes open to reveal a little stand up tuxedo, with your wedding party members name and title personalized in each box.
41. Raw Steel State Shaped Bottle Openers
For those bridal parties full of state pride, these super cute state cut out bottle openers are a great gift to include with a groomsman proposal card! Each bottle opener is cut out of raw steel with a magnet on the back, perfect for your groomsmen to store on a fridge door or in a workshop!
42. Personalized Groomsman Bottle Opener
Another great Bottle Opener option for your wedding party are these personalized corkscrew and bottle opener combos! Each opener is custom engraved with your groomsmen’s name, wedding role, and wedding date on its wooden handle, with over 9 designs to choose from to suit your style.
43. Laser Engraved Groomsmen Flasks
Groomsmen Flasks have so many affordable and beautiful options for your boys, I had to include a couple more! These flasks come in proposal gift boxes that are personalized for each groomsman, while the flasks themselves come in 20 different designs for personalization.
44. Groomsmen Proposals Flask Box
Looking for a great gift box for your flask proposal? Look no further than this dapper option, perfect for any DIY Flask or any of the flasks in this post! In fact, these are the gift boxes for the flasks above, but available on their own as personalized gift boxes! Each box is customized with your groomsmen’s name and wedding role, complete with a black and white tuxedo theme!
45. Groomsman Shot and Mini Bottle Proposal Box
I always love the pun for taking a shot at tying the knot, and I think any groomsmen would be happy to oblige with this adorable proposal box! While you’ll need to add your own shooter, each cube comes with the groomsman proposal inside the lid of the box, a cute personalized card stock bow tie with their name on top, and a shot glass inside.
46. Suit Up Mini Champagne Labels with Bow tie Straws
Dress up some mini champagne bottles for your boys with these adorable Mini Champagne Labels and Straw sets! Both the straws and bow ties come in several color options and each set comes with four labels, four bow ties, and four straws.
47. Groomsman Proposal Cigar Box
For a fun cigar themed Groomsmen Proposal, these cigar boxes are the perfect choice for your groom to pick his favorite stogie for each guy and gift them in this dapper box! Each box is finished in a red mahogany stain with a gold engraving, each personalized with your wedding date!
48. Groomsman Baseball Proposals
For those baseball loving boys out there, these proposals are a perfect pick! Each baseball is engraved with your boys name, wedding role, and your wedding date, perfect to propose to them during a friendly game or give as groomsmen gifts the day of!
49. Elegant Groomsmen Proposal Cards
For a classy and elegant groomsman proposal card, this card takes the cake! Its sleek and modern shape make it unique, and its beautiful lettering make it a classy choice for any wedding celebration!
50. Groomsmen Proposal Cigar Box
As my husband proposed to his own groomsmen in a cigar bar, these pretty cigar box proposals were just the thing to finish my groomsmen proposal gift list! These boxes come with either kraft or white paper card inserts and box tops, white the name and wedding party role personalized for each man in your party, perfect for proposing with each guys favorite cigar!
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