Groomsmen Proposal Ideas: Unique Gifts and Creative Ways To Assemble Your Wedding Party (or Show Thanks)

Gift-giving can be stressful.

Presenting a gift to someone as important as a groomsman makes the process even more mentally exhausting. Your groomsmen represent your best friends, your family, your ride-or-dies — those most important to you who’ll be there for you on your wedding day. The least you can do is find the best groomsmen boxes to convey your gratitude.

Groomsmen gifts might seem simple, but they need to be special, impressive, long-lasting, and, ideally, have an element of surprise. Of course, they don’t need to be in a typical box, but organizing the items in a container adds a touch of tradition.

Considering all the relevant criteria, it’s clear that a groomsman box can present quite a challenge for the groom, who already has a lot on his plate regarding wedding planning. Fortunately, there are plenty of groomsmen gift set ideas that check all the boxes. This article lists some of the best options to help you hand over an incredible gift and impress your groomsmen on your big day.

The Role of Groomsmen Boxes in Wedding Celebrations

Most of all, the groomsmen box shows your appreciation for the people who have been there for you before your wedding day and will continue to support you in the future. The best time to give it as a thank-you gift is during the bachelor party, rehearsal dinner, or on the wedding day. But don’t wait for the wedding party when everything is almost over. Dedicate a bit of time before the wedding to spend with your best buddies, calm pre-wedding jitters, reminisce, and talk about what the future holds.

Beyond just a thank-you gift, a groomsmen gift box set can also be given as a groomsmen proposal box long before the wedding. While some may already anticipate the proposal, you can still make the gesture extra special with a thoughtful groomsmen proposal gift, complete with a personalized groomsmen proposal card!

Typically, the gift for your best man will be a smidgen more special than those you give to other groomsmen — but it all depends on your preferences, the size of your wedding party, etc. Bigger weddings with over 100 people typically have between five and eight groomsmen which may consist of extended friends, relatives, or the bride’s father, brother, and other relatives. Therefore, some of the members won’t be as special to you as your best man, who should be someone you can’t have your wedding without.

What to Look For in a Groomsmen Box

Groomsmen's gifts should satisfy certain criteria.

Uniqueness

Ideally, they should be personalized and unique. You definitely shouldn’t just go for the first groomsmen box that pops up on Amazon. Think of the times you spent together with your friends and how the gift could feel special for both you and them. If you’re not going for a silly, fun gift like personalized bobbleheads, try to make it a bit sentimental.

Usefulness and Personalization

If fun or sentimental isn’t your cup of tea, choose a gift box set that’ll serve the groomsmen well for a long time to come. The usefulness aspect should be respected regardless of the tone you’re going for with your gift. Otherwise, it might sit on their shelf collecting dust or be re-gifted.

One way to be certain that the gift sets will be useful is to match them with each groomsman’s interests and preferences. Personalized groomsmen gifts feel even more special and ensure the groomsmen know you put much thought and effort into creating them. Still, while that might be the best groomsmen gift solution, it also creates several new challenges. You need to match each gift box set in terms of cost, quality, and thoughtfulness. You won’t be disclosing the price or origin of your gift, but your groomsmen might figure it out on their own and feel less special if their gift is lower in value.

The best option is to have the gift sets personalized with the groomsman’s name or initials. If you’re going for something that comes in multiple colors, you can also change them according to their style and preferences.

Types of Groomsmen Boxes

Contents of groomsmen boxes can vary — from playing cards to bourbon-flavored toothpicks, the packages typically include several items that are well-coordinated and follow a certain theme like personal hygiene, drinking, parties, summer vacation, etc. However, they can also be just one item, like a whiskey decanter or a personalized, high-quality flask.

No matter the theme you’re going for, remember to set a budget for yourself.

All-in-One Themed Gift Box Sets

All-in-one sets are popular groomsmen gift boxes due to their practicality and versatility.

If the theme is booze, consider a personalized whiskey decanter set engraved with each groomsman’s name and the date of the wedding. Or, choose to engrave the box or the glasses.

Flasks are another possible option for groomsmen who love drinking, especially if they travel a lot. Typically made from steel, flasks can be coated in wood or leather for a better grip and a more sophisticated look. You can also engrave the flasks with groomsmen’s names, initials, or other words to indicate their ownership.

Cigar sets are a perfect gift for groomsmen who smoke. They usually contain one or two cigars while the rest of the box is filled with other goodies like a lighter, tiny bottle of spirits, or matches.

Personalized Groomsmen Boxes

Although most of the groomsmen’s gift boxes are versatile, it’s important to recognize the personalization factor. Placing the name or initials of your groomsmen on the box or even on the items inside makes the gift feel extra special and lets your buddies know that you took your time creating their gifts.

Aside from whiskey decanters, flasks, and the boxes themselves, you can personalize various other items. Here are some fun ideas:

• A personalized pocket knife: Ideal for outdoorsy types, a stainless steel knife will last a lifetime. The groomsmen’s initials can go on the handle made from premium wood. The box for the pocket knife doesn’t have to be large, but you can also pair the blade with a flask, minimalist wallet, leather sheath, and other items to fill a standard-sized gift box.
• Personalized golf balls: If you’ve met your groomsman playing golf — or they simply enjoy the game — a golf ball gift set personalized with their name has lots of potential. In the set, consider including 12 golf balls, 12 golf tees, and 12 golf pencils. You can select the color of the balls, add a name or a monogram to print on the balls and the box, and choose the box’s material.

Perhaps the best groomsman gift is a bit of everything. If all other ideas elude you or you want to mix things up, consider including several items made specifically for each groomsman with items like a rocks glass with a custom name, a customized bottle opener, sunglasses, and personalized wedding socks.

Wedding Outfit and Accessory Gift Boxes

Besides getting your groomsmen gifts, you need to think about what they’re going to wear at the wedding. Since you might be the one who’ll need to provide the accessories, why not combine them with the groomsmen’s boxes and give them custom wedding cufflinks engraved with their initials?

When choosing the cufflinks, consider how they look on the groomsman and best man's suit since they might be wearing the same outfit. And, since you might be asking “Should the father of the groom match the groomsmen?” The answer is usually yes — the wedding attire should be the same as the groomsmen.

Luxury Groomsmen Boxes

While the price doesn’t determine the quality or value of the gift, grooms with a bigger budget may choose more luxurious groomsmen gifts.

Professional stylist, Donnell Baldwin, said “The best thing is to give a great-quality watch that you know your groomsmen will be proud to wear on the wedding day and beyond.” In fact, he recommends a 34mm gold-tone and textured-leather Timex Marlin watch. You may even have the option to personalize the groomsmen’s watches with their initials on the watch strap, but even without it, they’ll appreciate a cool and stylish watch.

If you liked the idea of a cigar box but want to step it up a notch, premium cigars like Arturo Fuente Breva Royal will make any cigar aficionado swoon. If you have multiple groomsmen who would love this gift, instead of gifting the entire box to one groomsman, you can divide the cigars and put them in empty cigar boxes that offer various customization options.

Grooming Gift Boxes

A high-quality cologne set from a brand you know your groomsman loves will surely find a purpose in his life. For example, this Ralph Lauren Polo Classic Eau de Toilette gift set might be just what he needs. Inspired by a vintage men’s flask, these three spray bottles make quite a first impression. The cologne’s pine, leather, tobacco, and patchouli notes will smell amazing regardless of the groomsman’s style and preferences.

A personalized shaving kit is another luxurious gift you can’t go wrong with. Whether one or all of your groomsmen have thick luscious beards or like to stay trim, this Marigold & Grey “Dapper Dude” shaving kit is sure to impress. It features a luxury shaving cream in a cedarwood and sandalwood scent, a wood shave brush, a leather trinket tray that you can monogram, and several complementary items that complete the package. To make the gift even more personal, you can include a handwritten note card.

Gamer Lover Gift Boxes

For your groomsmen who love to play table games, a leather poker set is an ideal gift for hosting game nights. Inside the box, consider including decks of playing cards, poker chips, and a pebbled leather case with soft suede lining that can be monogrammed to make the gift more personal.

Making Your Wedding Day Extra Special With Groomsmen Boxes

While the wedding day is all about the future newlyweds, a groomsmen box can make your buddies feel special and more like part of your wedding. A well-chosen gift goes a long way and ensures your best friends remember you whenever they look at your gift.

Make Your Groomsmen Feel Special With Unique Gift Boxes

While your wedding day is all about you, groomsman's gift boxes make your friends feel special and more like part of your wedding.

Remember: A special gift for your groomsman doesn’t have to be expensive. Sure, it can be on the more luxurious side, but the best groomsmen box sets are unique, useful, and thoughtful. Personalized items are the way to go if you want to make them extra special.

When choosing something the groomsmen will wear on the big day, ensure it matches their wedding attire. Generation Tux offers groomsmen rentals that ensure your wedding party enjoys your big day in style. Including clothing items and accessories as part of your groomsmen's proposals is a great idea, as it sets the tone for the engagement party and the overall wedding. A groomsman proposal gift, especially when it includes a thoughtful card, can create excitement ahead of your wedding day.

Ready to get gifting? Kill two birds with one stone and organize your groomsmen’s outfits, too!