You’ve popped the big question to your other half, and they said yes, they’d marry you. Now it’s time for the next proposal: asking your friends to stand by your side on the big day.
But how to do it?
Whether you’re going sentimental, funny, or all-out grand, there are plenty of thoughtful groomsmen proposal ideas to help you make the moment memorable. The right groomsmen proposal gifts will show your friends just how much they mean to you.
Not sure where to start? We’ve gathered our favourite ways to ask, some ideas for groomsmen proposal cards, plus tips on when and how to do it right.
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How to Propose to Groomsmen
Before we get into the gifts and creative ideas, let’s start with the basics: what exactly is a groomsmen proposal?
The second-most important proposal you’ll be making in your life, asking someone to be part of your wedding party is a meaningful gesture. It’s a way to formally invite the people who’ve been important in your life to stand by your side on the big day.
But there’s a bit more to it than simply asking the question. Some things to consider:
Choose the Right Timing
You should already have a clear sense of the date, venue, and overall vision for the wedding. Asking once those key pieces are in place makes the proposal feel more thoughtful and intentional. At the same time, try not to wait too long. Groomsmen may need to plan for travel, events, and yes, suits.
Ask in Person, Whenever Possible
Being face-to-face makes the moment more genuine and gives you the chance to share your excitement. If distance makes that tricky, ask over a video call. It’s not a question that should be relegated to a text message.
Be Clear About Expectations
It’s not all champagne and cufflinks. Let them know what being a groomsman will involve, from helping plan the bachelor party and attending fittings, to clarifying any costs involved. This can help avoid awkward conversations later.
Make it Personal
Adding a gift makes the moment even more memorable, even if it’s something small and meaningful that speaks to your shared history.
Groomsmen Proposal Ideas For Every Type of Friendship
Now that you’ve got the foundations in place, let’s explore some stylish and creative groomsmen proposal ideas.
Groomsmen Proposal Gifts and Ideas
A tie or pocket square
Get each of your groomsmen an accessory that matches the colour scheme of your wedding. It’s a stylish way to unify the groom’s party look, and a useful gift that they can use again in the future.
Custom cufflinks
Chances are, your groomsmen will be wearing cufflinks on your wedding day, so you should all be matching! They could be engraved with initials, your wedding date, or an inside joke or memory that means something to you both. Again, it’s an endlessly reusable gift for them, too!
Directions to the nearest tailor
For a charming gift that’s also very practical, give your groomsmen a handwritten note with your proposal, and include the address or business card of a trusted tailor. It’s also a win for you — ensure everyone’s looking sharp from the first fitting.
Simple Groomsmen Proposal Ideas
Want to keep your proposal a little more low-key? Here are some simple yet menangful ideas.
A cigar
An old-school symbol of manliness and strong brotherhood, a single, well-chosen cigar can be a great way to toast to what’s ahead. You could even ask them to hold off lighting up until after the wedding, when all the groomsmen can smoke them together.
A flat cap to wear on the day
For weddings with vintage flair or countryside charm, gifting a flat cap gives your groomsmen something both practical and on-theme. It’s especially fitting if you’re considering tweed suits for the groom's party.
A handwritten note
Sometimes, all you need is sincerity. A personal note expressing why you want them by your side can mean just as much (if not more) than any gift. It’s a small gesture, yes, but it will make a lasting impression.
Unique Groomsmen Proposal Ideas
Asking your best mates to be by your side on your Big Day is a big deal, so why not making the proposal unique and memorable?
Bouquet of liquor
Swap roses for mini bottles of their favourite spirits, arranged like a boozy bouquet. They’re easy to make; just affix the bottles to sticks and arrange them into a vase or pot like flowers. It’s unexpected and sure to get a smile.
Engraved bottle
Instead of a standard invite, have it engraved on a bottle of whiskey, gin, or whatever your mate prefers. It’s part proposal, part keepsake, and will look great sitting on a shelf long after the wedding.
Monogrammed socks
Ask your groomsmen to put their best foot forward, literally. Custom socks with their initials or your wedding make for a thoughtful, wearable gift. Bonus points if they coordinate with your wedding colours and suit style.
Funny Groomsmen Proposal Ideas
Up for a laugh? Take the pressure off your groomsmen proposal with a funny gift.
Wedding recovery kit
No one is going to party harder at your wedding than your groomsmen. A wedding recovery kit could include essentials like painkillers, sunglasses, mints, and even a hydration sachet. It’s practical and funny — and might even come in handy after your bachelor party, too.
Hilarious cards
If you consider yourself the funny one of the group, lean into that with your proposal. There’s no shortage of cheeky proposal cards out there: think “I can’t tie the knot without you,” or “this could have been a text, but she made me give a gift.” Pick one that suits your sense of humour (and theirs), or write your own with an inside joke.
A booklet on ties and knots
A tongue-in-cheek educational “guide” to mastering formalwear is part humorous, part helpful. It’s a lighthearted way to get your groomsmen ready for the big day, especially if your group isn’t exactly known for your sartorial know-how.
DIY Groomsmen Proposal Box Ideas
Alternatively, you can make the proposal feel even more personal by making the gifts yourself.
Picture frame
Gift each groomsman a high-quality picture frame, and include a snap of you both, either a recent photo or one going back to when you first met. It’s a nice little keepsake, especially for any of your particularly sentimental friends.
Cologne
If you know his favourite or signature scent, buy a small bottle of that. Or pick a classic, refined scent and include a note saying: “Wear this when I say ‘I do.” It’s a stylish move and ensures your groomsmen smell as good as they look.
Shot glasses
A custom shot glass adds a bit of fun to your proposal — and can be used on the spot for an early toast! Have it engraved with their name, the wedding date, or simply “Groomsman.” You can use them at the bachelor's party, too.
Grooming kit
Help your mates look their best with a compact grooming kit: think beard balm, mini scissors, or a comb. Again, it’s practical and gives a nod to the dapper look you’ll be going for on the big day.
The Ultimate Groomsmen Proposal Idea
If you want to go all out with your gift, consider this: buy them a custom suit that they can wear as they stand with you at the altar.
Weddings can get expensive for guests, even more so if you’re part of the groom’s party. With the gift of their wedding suit, you’re inviting them to be part of your day while also giving them a lasting outfit in their wardrobe.
Regardless of whether it's a relaxed summer affair that calls for a breathable linen suit or a countryside ceremony that screams tweed, you’re giving them something both personal and practical.
Groomsmen Proposal Message Ideas
Once you’ve chosen the perfect gift or proposal idea, don’t forget to write out a thoughtful message to seal the deal. It doesn’t matter if you’re penning a handwritten card or gift tag, or if sending a text is more your speed, your words should reflect your personality and your relationship.
Here are a few ideas, whether you're going classic, keeping it light, or just getting straight to the point.
Classic
- “It wouldn’t be the same without you. Will you stand by my side as a groomsman?”
- “A great friend deserves a great role. Will you be my groomsman?”
- “Your friendship means the world. I’d be honoured to have you as a groomsman.”
Funny and Lighthearted
- “Free suit. Free drinks. Mild responsibility. You in?”
- “Help me get to the altar without losing my tie (or my mind). Be my groomsman?”
- “Because every groom needs a solid crew — and someone to buy the drinks if things go south.”
- “You're not just invited to the party, you’re part of the chaos. Groomsman?”
Simple and Direct
- “Big day’s coming. Suit up?”
- “Want to be one of the guys in suits standing next to me?”
- “Need a wingman. Interested?”
Shop Groomsmen Proposal Gifts
At Tweedmaker, we’ve got the fits and accessories to suit every wedding vibe. Explore our full collection and start planning a look that you and your groomsmen will be proud to wear on the big day and beyond.
