Guys, how do you pop the question to your best buddies who will stand by your side as you take the next big step in your life? A groomsman box, of course!

“Will you be my groomsman” boxes are gaining in popularity, becoming a fun, personal, and memorable way to ask your friends to join you at the altar as you take your wedding vows. They’re also a great way to thank your buds in advance for taking the time and effort to help you pull this important day off without any problems. They’ll be there for you as moral support, and make the day more fun, too, so why not get your best man and  groomsmen excited for the big day with a unique, personalized gift box?

Pinterest is a wealth of ideas for both what to include in your groomsman boxes and how to pull off the presentation. And as you scour the web, you’ll find four main things that you should consider including in your gift boxes. But let’s start with the groundwork.

groomsman box with best man box

Start by setting a budget

Your budget will depend on many things, but one thing every groom must consider is the number of groomsman boxes he needs to make. Make sure to include your best man, all our groomsmen, and your ring bearer (although his box might include different contents). Once you know how much you can spend, you can move on to figuring out what to include in your groomsman boxes and how much effort and DIY you need to put in.

Once the budget is set, you need to consider four things when putting together the perfect “Will you be my groomsman” boxes.

1. A clever way to pop the question

The main purpose of the groomsman box is to ask the question ” Will you be my groomsman/best man/ring bearer/usher, etc.?” Options include doing it with a card, a handwritten note, a sticker you can affix to the box, one of the gifts inside the box, or another idea entirely. We’ve seen everything from classy and elegant to hilarious and sentimental. How you choose to ask your groomsmen comes down to your personality (and the personalities of your friends) and how you want to set the tone.

You can even use beer to pop the question!

2. Something to help them celebrate

Speaking of beer, some type of celebratory beverage is customary and will be much appreciated by your groomsmen. Some grooms include beer and small or mini bottles of liquor. Others give out a cigar, or even chocolates, nuts, and candy to help them celebrate. In addition to food and drinks, including something the guys can keep as a souvenir of your wedding day adds a nice touch to your gift. Things like a flask, bottle opener, or personalized glass will be well received.

3. Something personalized just for them

Adding something extra also lets you create a meaningful, personalized gift that your guys will appreciate. This should be the main part of your gift, as this will be what your friends will keep, use, and enjoy once the wedding festivities are over.

Some popular personalized groomsmen gifts that are perfect for DIY ‘Will you be my groomsman boxes’ include:

Engraved cigar case and cutter set

This is a great gift if you’re planning on including cigars in your gift boxes. Have their name, nickname, or monogram engraved on the case, and you know your guys will be lighting up in style on your wedding day. You can also include a personalized Zippo lighter, engraved with names and wedding date.

Personalized whiskey glasses

Another great option for a personalized groomsman gift is custom drinkware. Whether it’s a whiskey glass, beer mug, or shot glass, give your men a great way to enjoy their favorite beverage and, at the same time, take home a nice memento from the wedding.

Custom watch box

If you want to give your groomsmen something practical, personalized, and a bit more expensive, look no further than a beautiful leather watch box. This is especially nice if you know your friends like wearing watches, and it’s something they’ll be able to keep and use for a long time.

Of course, you have plenty of other great groomsmen gift options, from small, inexpensive gifts, such as a personalized bottle opener or set of custom printed golf balls, to something more fancy, such as a custom pocket watch or set of engraved cuff links.

4. Something personal

The final piece of your groomsmen boxes should be something personal. It can be an inside joke, a reference to a memory you two share, or anything else that’s meaningful and personal. The reason you should include this last piece is that while the gift box itself is a nice gesture, adding a small, personal touch will make a lasting impression.


Kasia Lorenc is a writer and editor at Personalization Mall, covering gifting, home decorating and more.

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