DIY Groomsmen Boxes

*Some of these links in this DIY Groomsmen Boxes post are affiliate links (marked by an asterisk), meaning if you purchase something through the link, I receive a small percentage of the profit. This does not cost you more money at all. All of the products/events I stand behind and my opinions havenโ€™t been swayed at all.

Let me preface this post by saying that I was incredibly proud of my DIY Bridesmaid Boxes, but I hate to admit that Stephen blew me out of the water with his DIY Groomsmen Boxes. I don’t actually mind admitting that though, because I craft all the time and I tend to not perfect things as much as I used to. However, Stephen crafts maybe 3-4 times per year, and when he does, he absolutely nails what he’s doing.


For his groomsmen proposals, he decided to make Groomsmen Survival Kits, which I thought was a phenomenal idea. He took into account each one of his groomsmen’s tastes and styles, and his style,ย  and meshed them into a box.

So, lets get right into it. This post is going to be very photo heavy, since those are some photogenic boxes ๐Ÿ™‚

Stephen started with these wooden boxes from Michaels. (Similar boxes can be found here*,ย  here*, and here* on Amazon).

DIY groomsmen boxes

To get the effect that he has on the boxes (pictured below), he used a screw driver to dig grooves into the boxes.

Then, he stained the wooden boxes with a dark stain* and did a very light sanding (200 grit), followed by a heavy sanding with steel wool (#00). He sanded the middles and sides to give a more worn effect.



I mean, just look at that texture and contrast. The way the dark stain highlights the grains and crevices–just beautiful.


Idea for Groomsmen Proposal

I love all the texture and movement happening in that wood.

Next came my contribution to the project: the stenciling. Since I have my favorite crafting tool on hand, the Silhouette Portrait*, I made Stephen’s vision for the top of his box come to life. The Portrait allows you to design a stencil in their software, and then cuts it out on a medium of your choosing (we used vinyl for this project). After searching for the perfect font (Stencil Cargo Army) and finding an outline of a skull and bow tie that he liked, I designed the stencil in Photoshop and imported it into the Silhouette software.

After it was cut, I stenciled the tops of the boxes with white paint.

Groomsman Survival Kit


Even though I was the one operating the Portrait, Stephen still gets all of the credit for this design. He told me which font to use, gave the “OK” on the skull and bow tie, and even sent me through a few rounds of edits before I even began cutting. He had 100% creativity, I just had the execution ๐Ÿ˜‰

Rustic Groomsman Boxes


After the paint from the stencils dried, he sealed/protected the boxes with a matte clear acrylic finish.

Now for the inside of the boxes, which are just as impressive as the outside (if not more impressive). He put a lot of thought into the contents of the boxes, and what his groomsmen would need on the day of and after the wedding.

He started by personalizing a flask for each groomsman with their name, their role, and the date of the wedding. Similar flasks can be found here*, and here.

Personalized Groomsmen Flask

Then, he shopped for each of their favorite alcohol, in airplane bottle size.

Jack Daniels Wedding

The rest of the contents of the boxes were the same, and included: Axe body spray, mouthwash, a cigar, Pepto, Aleve, Vitamin C and gum. Yep, he crammed a lot into those boxes!

Wooden Groomsmen Boxes




The groomsmen are sure to have everything they need for our big day, and they’ll be smelling awesome too, which is a perk for everyone ๐Ÿ™‚

And for my favorite part: the details. I love the ideas that Stephen thought of when it came to actually “popping the question” so to speak.

First, he framed this on the inside of the top of the box, which he designed in Photoshop:

Groomsmen proposal ideas


Then, he designed this “Top Secret” letter for them, which he aged by soaking them in coffee, then letting them dry out.



I really, really love those: especially the section at the bottom that says “Status: Blushing Bride” and “Status: Galant Groom.” So awesome.

Lastly, he found these tags at Michaels that were the perfect finishing touches for the boxes:

Will you be my groomsmen



I lent my handwriting to the tags, but the answers were all him. I was actually really scared that I was going to mess them up, especially since you can’t erase Sharpie. But, it turns out I did okay!

Once the tags were written out, he folded the “Top Secret” note up and place it, alongside the tag, in a little brown bag. I wrote “No. 1” for best man, and “No. 2,” No. 3,” and “No. 4” for the rest of the groomsmen.

Here are a few glamor photos of the boxes all put together:

Will you be my best man?




Overall, we were both thrilled with how they turned out. I love how much thought and detail he put into making this process special for his groomsmen. It’s so much fun watching this wedding unfold, and each and every step is another awesome memory that we’re making for ourselves and everyone involved in our wedding.

See you soon with more details on wedding planning ๐Ÿ™‚

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