The Ultimate Guide To Picking Your Groomsmen

No matter how involved with the wedding planning process you are, there’s one task that no man can avoid when helping to plan the big day—picking groomsmen.  

While it might seem like you can simply pick out your best mates and call it a day, there are a few considerations you’ll want to make when selecting your groomsmen. 

Not sure how to go about the process? From choosing the right men to what you should expect of your groomsmen, this ultimate guide answers all your biggest questions (be sure to check out our men's wedding attire guide after you pick your groomsmen)

Picking Your Groomsmen 

Depending on the size of your circle of friends and family, picking your groomsmen can either feel like the easiest task or impossible. 

If you land on the impossible end of the spectrum, we’re here to help. 

How many groomsmen should I have?

First things first, you have to know how many groomsmen you’re going to have before you can decide on who will stand with you. 

Oftentimes, how many groomsmen you have depends on your partner. If you have a bride who is deadset on having 6 bridesmaids, you better believe you’ll likely have to come up with six yourself to keep things equal on both sides (equal bridesmaids and groomsmen tends to look best for pictures). 

However, if you and your partner are attempting to come up with a number together, here are a couple of other factors that you can consider to help:

• How many guests you’re inviting to the wedding
• How intimate your wedding is going to be
• How many personalities you want to deal with on your wedding day 

Wedding Size: You’ve probably been to large weddings (200+ guests) and seen some small wedding parties, and you’ve probably been to smaller wedding that have large wedding parties. This is not a set in stone rule, but if you’re struggling, in general, the more guests you’re inviting, the larger your wedding party. Think about it: If you’re only inviting 100 guests and you have 10 people in your wedding party, that’s 10% of your guests that are standing in your wedding. On the other hand, if you have 300 guests and 10 people in your wedding party, this ratio makes more sense.   

Intimacy: When it comes to your big day, all brides and grooms have different expectations. For some, they want an intimate gathering with friends and family. For others, they want to throw the party of the year. If you land on the extreme of either end, this can help in determining wedding party size. For instance, intimate weddings will likely only include family in the wedding party and perhaps a best friend or two. On the other hand, those who want the big party atmosphere might include multiple friends and family in the wedding party to help bring energy to the big day. Consider the overall feeling you want your wedding day to have, and this can help you determine big vs. small wedding party. 

Personalities: Lastly, and probably most importantly, it’s important to remember that the bigger your wedding party, the more personalties you’re going to have to deal with. For some, if you have friends from different circles who don’t get along, this can be a lot to deal with, especially on your wedding day when you want to enjoy yourself. Of course if you have a close group of friends who are already friends and/or are laid-back, a big fun group might be perfect for you.  

So which is best? Small and intimate or big and over-the-top?

When it comes to small and intimate, benefits include: fewer personalties to deal with, easier communication between close friends, and a more intimate feeling on the big day. Some negatives of a smaller wedding that you might want to consider include: possibility of offending friends/family by not including them, less people to rely on/help with the wedding, and less people to enjoy the day with (i.e. getting ready, pictures, limo rides, etc.). 

If you’re thinking you want to go big with your wedding party, the biggest thing to consider is the number of personalities you’ll have to deal with. The more personalities to deal with means the more opportunity for drama. On the upside, though, if you’re a social couple and you like being surrounded by friends, you might have more fun with a larger wedding party. 

Having said all of this, at the end of the day, deciding how many groomsmen you have is a completely personal decision. You can go small and intimate or big and over-the-top. Whatever the case, we suggest going with the wedding party size that will suit you and your partner best.

How should I pick my groomsmen?

Once you have your number, follow these steps to picking your groomsmen.

Start with siblings

When considering your groomsmen, start by taking a look at your family members. For most, having your brother(s) as a part of your wedding party is the easiest way to add numbers without offending anyone (i.e. most friends will understand if you pick your brother over them).

You can also consider cousins, step-brothers, older nephews, or even your partner’s siblings if you’re close. 

What if I have multiple brothers?

Here’s where things can get tricky. Maybe you have one brother you’re closer with, or maybe you have 3+ brothers, but you also have friends that you would like to include in your party. 

If you have multiple brothers, but you don’t necessarily want to include them all in your wedding party, make an agreement on which brother will serve in what wedding. This way, all your brothers stand up in one wedding, but not necessarily all of them. 

Can my sister be a “groomsman”?

Yes! Absolutely. There’s no rule saying your sister can’t stand by you at your wedding. 

While she may not necessarily partake in all your groomsmen activities and she might prefer wearing a bridesmaid dress over a suit, if you want your sister standing with you on your big day, don’t be afraid to step outside what is conventional. 

Pick your best friends 

If picking your siblings doesn’t get you to the correct number of groomsmen, or you’ve opted to not include all of your siblings, you can start adding in your friends. 

How you go about this will largely depend on how many spots you have available and what your circle of friends is like. 

The easiest way to keep this clean and not offend anyone is to stick within one circle of friends. So, for instance, instead of asking your childhood best friend, your coworker, a friend you play football with, and your neighbour, stick within one circle of friends (i.e. the friends you spend the most quality time with and who know you best). 

Can I have a female “best man”?

Just as it’s totally cool to have your sister in your wedding party, it’s also totally cool to have a female “best man.” This can be your sister, but it also can be a friend. Remember, it’s your wedding and there are no set rules. 

If you’re still having difficulty narrowing down your groomsmen, the next best thing to look at is reliability and personality.  

For instance, if you have two friends who are equally important to you, but Jimmy is notorious for dropping the ball on important commitments, while Billy is a stickler for detail, it might be best to pick Billy over Jimmy. Sure, Jimmy might be upset, but if you’re at this point, there needs to be something to help you break the tie—reliability tends to be a good one. 

In addition, you also might want to consider personalities, and how personalities amongst the group will mesh. 

Perhaps you have two friends who don’t get along, or maybe you have a friend that your brother is not a fan of. While most adults should be able to pull it together for a wedding, if you’re still struggling with who to choose at this point, looking at your friends’ personalities will help you narrow it down. 

How to ask your chosen groomsmen

Now that you’ve chosen your groomsmen, it’s time to ask them. Here are three ideas to help inspire you when asking your chosen groomsmen to be part of your big day. 

Some of you might like to keep things straight-to-the-point and simple when asking your groomsmen, and there’s absolutely nothing wrong with that. 

More and more, we’re seeing elaborate ways of asking your chosen groomsmen, but if you don’t think your groomsmen will appreciate the gesture and/or it’s not your style, there’s no shame in simply asking without the big show. 

The only rule here—no emails or texts, ask in-person. When in-person is impossible because of distance, a phone call is your next best option. 

If you want to take it up a notch, there’s no shortage of groomsmen gifts out there. Some of our favorites include: 

• Personalized beer mugs/whiskey flasks 
• Something to wear on the big day (socks, suspenders, cuff links)
• A groomsmen “proposal box” (i.e. a collection of items and a note asking the question)
• Bottle of booze with a custom label 
• Cigars 
• Sporting equipment 

The main thing to consider when getting a gift to ask your groomsmen is the customization. If you’re going to go out of your way to get a gift, customizing with a name or adding something that asks “will you be my groomsmen” makes the gift feel special. 

And lastly, if you really want to step it up when asking your groomsmen, you can bring all of them together for an event (i.e. sports, concert, camping), you can record a silly video that proposes the question, or you can even write a song if you’re musically inclined. 

For the last two options, you’ll likely want to keep it light and on the more humorous side. You can find plenty of examples on Youtube if you need inspiration. 

What should you expect of your groomsmen? 

With every wedding and every friendship group, there will be different expectations set for groomsmen. Having said that, if you’ve never been a part of a wedding party or you need a refresher, here are some general guidelines of what you should expect from your groomsmen:

• Generally, most groomsmen don’t have too many responsibilities to attend to before the wedding day. Instead, most responsibilities will fall on the wedding day. 
• Planning some sort of bachelor party or small gathering may be required of the best man. 
• Groomsmen should be responsible for looking presentable on the big day. This includes getting a hair cut, shave, and/or beard trim before the wedding day. 
• The best man may be responsible for holding onto the rings before the ceremony. 
• Groomsmen may be expected to be ushers for the ceremony, showing guests to their seats. 
• Designated groomsmen may be expected to give a short speech at the reception; however, forcing your friends to do this might not be best. Instead, try asking which of your groomsmen is comfortable with public speaking. 

In general, simply relying on your groomsmen to be there for moral support on your wedding day is the most important task they’ll complete. We recommend not asking too much or placing too many responsibilities on your groomsmen. This can lead to tension, and ultimately, might impact your relationship leading up to the wedding. 

How to set your groomsmen up with attire

Traditionally, groomsmen are expected to pay for their attire. 

With that in mind, it’s important (and considerate) to consider cost when choosing your suits. Remember, if you have a large group, you’re likely dealing with different budgets, and asking some of your friends to spend large sums of money might be a sore spot.

To ease some of the burden here, gifting suit accessories is always an appreciated gesture. For instance, buying all your groomsmen their ties, or keeping it classy with matching suspenders. 

Whatever the case, while you’ll certainly want to ensure you pick a high-quality suit that matches the formality of your event, it’s always considerate to factor in budget. 

How should I thank my groomsman after the wedding?  

And lastly, now that the wedding is complete, you’ll want to thank your groomsmen for standing up with you. To do this, you can keep it simple or go for something more elaborate. As always, though, being courteous and extending some form of appreciation is highly recommended. 

Here are some ideas to spark your inspiration: 

• Keep it simple with a hand-written note and personalized card (i.e. a photo of your group of groomsmen, for instance). 
• Speaking of a photo, you can also choose to have one of your photos printed and professionally framed.
• Plan a boy’s night out after the wedding to celebrate (dinner, sporting event, game night at home, pub crawl, etc). 

Beyond that, you can take a look at any of the gift ideas for asking your groomsmen (above) and use those as thank you gifts as well. You certainly don’t have to go all out and get multiple gifts both for asking and thanking, but the little touches will go a long way here.  

Bottom line

Your wedding day is an important event in your life, and deciding who is going to stand by your side to celebrate is worth taking the time to consider. We hope some of the tips from above make your decision that much easier. 

Cheers to a stellar wedding party, a beautiful wedding day, and most importantly, a happy marriage!