Last week we shared our 4 must-haves in a perfect “Will you be my bridesmaid?” box. This post is all about the guys and how to pop the question to your best buddies who will stand by your side as you take the next big step in your life.

“Will you be my groomsman” boxes are gaining popularity, becoming a fun, personal and memorable way to ask your friends to join you at the altar as you take your wedding vows. It’s 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 to 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?

As we mentioned in the bridesmaid box post, Pinterest is a wealth of ideas on both what to include in your groomsman boxes and how to pull off the presentation. And as you scour the web you’ll find that there are four main things that you should consider including in your gift boxes. But first, let’s start off with the groundwork — your first step to creating your own “Will you be my groomsman” boxes is to figure out your budget.

Always Start With Budget Planning

Your budget will depend on many things, but one thing that every groom will have to consider is how many groomsman boxes are you putting together. Make sure to include your best man, all of 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 contribute.

Similar to the bridesmaid boxes, there are four key things to 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. So naturally, this is where you should start. Whether its with a card, a handwritten note, a sticker you can adhere to the box or one of the gifts inside the box, or another clever way, don’t forget to include this vital part. We’ve seen everything from classy and elegant to hilarious and sentimental. It really depends on your (and your friends’) personality 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 well appreciated by your groomsmen. We’ve seen grooms include beer and small or mini bottles of liquor; you can get a wide variety these days. You can also include a cigar, or even chocolates, nuts and other edibles to help them celebrate. We’ve even seen groomsman boxes with nothing but liquor, cigars and chocolates, but in our opinion adding something that the guys can keep as a souvenir of your wedding day adds a nice touch to your gift. Even if it’s something as simple as a flask, a bottle opener or a personalized glass.

3. Something Personalized Just For Them

Adding something extra also gives you the opportunity to create a meaningful, personalized gift that your guys will appreciate. This should really be the main part of your gift, as this will be what your friends will keep, use and enjoy after 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. You can have their name, nickname or monogram engraved right on the silver cigar case and you know your guys will be lighting up in style on your wedding day. If you want 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 its a whiskey glass, a beer mug, steel tankard or even a shot glass, you can give your men a great way to enjoy their favorite beverage and at the same time, have a nice memento from the wedding.

Custom watch box — if you want to give your groomsmen something practical, personalized and a bit more expensive, you can customize a beautiful leather watch box. This is especially nice if you know your friends like wearing watches and it’s something the’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, like a personalized bottle opener or a set of custom printed golf balls, to something more fancy, like a custom pocket watch or a 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. Why include this last piece? While the gift box itself is a nice gesture, that small, personal touch you add will make the lasting impression.


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

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