Groomsmen Proposal Guide: How to Pop The Question

Groomsmen Proposal Guide: How to Pop The Question

So you’ve proposed to your other half, and you’ve got the yes – congratulations! 

But now that the wedding proposal is out of the way, it’s time to turn your focus to something as equally important. Have you considered your groomsmen proposal yet? 

Rather than just asking your groomsmen out of the blue to be a part of your wedding, why not get a little creative. Do something memorable that you and your groomsmen will cherish forever –– you don’t have to save all the grand gestures for your fiancé!

More and more grooms are choosing to pop the question to their potential groomsmen in fun and innovative ways, which is far more interesting than just flicking off a group text. We can do better than that!

Let’s go through some of the best ways to ask your groomsmen to join you at the altar on the most important day of your life. 

Creative ideas for groomsmen invitations


Personalise a matching gift for everyone

Customised flasks are a classic gift for groomsmen, and with good reason! 

Engrave a classy metal flask with “best man” or “groomsman”, their initials, and the date of your wedding. It’s not only a gift they’ll hang on to forever, but will bring back good memories of the big day – and your proposal – forever. 

Gift them a cigar

A cigar still stands as a strong symbol of manliness and of brotherhood, making it the perfect gift for your future groomsmen. 

Gift it to them with a handwritten note on quality stationary, asking them to be there with you on your wedding day. 

You could even make a pact to smoke the cigars all together after the wedding, adding an extra level of sentimentality. 

Create custom cufflinks


Chances are your groomsmen will all be wearing cufflinks on your wedding day, and of course you should all be matching! Why not pop the question by giving each member of your groom party a pair of custom cufflinks as a way to show your gratitude in advance? 

They could be engraved with their initials, the date of your wedding, or a phrase that means something to you. 

Speaking of wedding day attire….

Buy their suits 

Weddings can get expensive for guests, and even moreso when you’re a part of the wedding party. As a way to show your appreciation for your groomsmen, you can’t go past buying a suit for them. 

You could surprise them by inviting them to a suit fitting, where you’ll ask the big question. If you’re not going full black-tie, consider our tweed suits as a striking option for your groom party. 

We guarantee our custom suits will be the perfect fit –– and look perfect at the altar. 

Engrave their invitation on a bottle 

Paper invitations just get stuck to the fridge for a few months and are eventually thrown out. 

Give your groomsmen an invitation they’ll hang on to forever by engraving it into a bottle of their favourite spirits. There are many services that can engrave into glass bottles –– you can write out a formal invitation, put their last name, or just engrave an insignia that means something to you all, like deer antlers if you’re all into hunting. 

Get them a wedding recovery kit

Your wedding is likely to be a huge night to remember, and there’s no one who will celebrate more than your groomsmen. Put together a kit with things like painkillers, a razor, comb, breath mints, or eyedrops. 

Present it with a thoughtful note about how you’d love them to join you as a groomsman –– and have a massive night to remember for the ages!

Once you’ve got your groomsmen on board, it’s time to start planning the big event! From the venue and date to flowers and seating arrangements, we know that wedding planning can be pretty overwhelming. 

But when it comes to finding a suit for yourself – and your newly-recruited groomsmen – the answer couldn’t be more simple. A classic tweed suit is the perfect wedding outfit for the modern gentleman. Tweed was born to be worn down the aisle: it’s comfortable, stylish, and suitable for all dress codes. 

Browse through our tweed wedding collection to get inspired, then we can get started on crafting you the perfect wedding suit! 

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