How to Order Custom Shirts for a Group Without Guessing Sizes

From collecting sizes to choosing fits and quantities, here’s how to make sure everyone gets something they’ll actually wear.

Ordering custom shirts for a group sounds simple enough. Pick a design, choose a color, collect everyone’s sizes, and you’re good to go. Right?

Well, anyone who’s ordered shirts for a company, school, sports team, or family reunion knows there’s a little more to it.

One person wants a medium. Another says they wear a large, but only in certain brands. Someone needs a youth size, three people haven’t responded, and suddenly you’re wondering whether to order ten extra XLs just in case.

The good news? Ordering custom apparel for a group doesn’t have to be a guessing game. With a little planning, you can keep everyone comfortable, avoid wasted inventory, and make the entire process much easier.

Here are seven tips to help you get your group apparel order right the first time.

1. Stop guessing everyone’s size

When you’re ordering 50, 100, or even 500 shirts, it’s tempting to estimate how many smalls, mediums, larges, and XLs you’ll need.

While standard size distributions can help when ordering promotional giveaways, they’re not ideal when you know who’s receiving the shirts.

Think about it: Your office staff, little league team, and family reunion attendees probably have very different sizing needs.

The better approach? Ask people what they actually wear.

Whenever possible, collect individual sizes rather than relying on a generic bulk shirt size breakdown. Encourage everyone to check their measurements against a garment-specific size chart instead of simply choosing their usual size.

You’ll get a more accurate order, fewer disappointed recipients, and fewer leftover shirts collecting dust.

2. Choose the garment before collecting sizes

Here’s a mistake we see people make: collecting everyone’s sizes before deciding which shirt they’re ordering.

Not all medium T-shirts fit the same!

A medium from one brand might have a relaxed, roomy fit, while another brand’s medium might be slimmer and more fitted. Fabric, cut, and garment weight can all change how a shirt feels.

Before sending out your custom t-shirt sizing guide, narrow down your options.

Consider these factors:

• Fit: Relaxed, standard, or athletic?
• Fabric: Cotton, polyester, or a soft blended material?
• Weight: Lightweight and breathable or heavyweight and structured?
• Style: Unisex, women’s, youth, or a combination?

For a deeper dive into fabric choices, check out our guide on choosing the right garment weight for your custom T-shirts.

Once you’ve selected your garment, share that specific manufacturer’s sizing chart with your group. If possible, provide sample shirts so people can try them on before committing.

Not sure how different shirt sizes compare? Check out the BELLA+CANVAS size guide as an example of how garment measurements can vary by style.

A little preparation here can prevent a whole lot of sizing headaches later.

3. Make collecting sizes ridiculously easy

If you’re still texting 75 people individually to ask what size shirt they wear, there’s a better way.

A simple online form can save you hours of back-and-forth communication.

Google Forms, Microsoft Forms, or a shared spreadsheet can help you gather everything in one place.

Your form should include:

• Name
• Preferred garment style, if applicable
• Shirt size
• Quantity needed
• Any special sizing requests

Include a link to the actual product’s size chart, and set a firm submission deadline.

For example: “Please submit your shirt size by Friday at 5 PM. After that, we can’t guarantee your preferred size.”

You can even send one reminder a few days before the deadline instead of chasing everyone individually.

Pro tip: Use a spreadsheet to track responses and calculate totals automatically. That way, you’ll know exactly how many shirts you need in each size when it’s time to place your order.

4. Offer options without making things complicated

Giving everyone a choice sounds great until you’re managing six shirt styles, eight colors, and 14 different size combinations.

More options aren’t always better.

For most group apparel orders, we recommend keeping things simple. Start with one versatile unisex shirt, then consider adding a second fit option if your group would appreciate it.

For example, a company ordering shirts for employees might offer:

• A classic unisex T-shirt
• A women’s fitted or relaxed-cut T-shirt

Keeping the design and color consistent across both styles helps maintain a cohesive look without turning your order into a logistical nightmare.

Just remember that different garment styles may have different sizing charts, availability, and pricing.

The goal is to give people enough choice to feel comfortable without making the ordering process unnecessarily complicated.

5. Don’t forget extended and youth sizes

One of the easiest ways to make people feel left out of a group order is to overlook their sizing needs.

Before finalizing your garment selection, check whether your chosen shirt comes in the full range of sizes your group might need.

Some styles offer youth sizes, while others extend through 3XL, 4XL, or beyond. Availability varies by manufacturer, style, and color.

Also, keep in mind that extended sizes may cost a little more, so factor that into your budget early.

If you’re ordering shirts for a school, sports league, or family event, youth sizes deserve special attention. A youth large isn’t necessarily interchangeable with an adult small.

Our advice: Make it easy for people to request the size that works for them without having to explain their needs publicly.

Everyone should feel good wearing their custom apparel!

6. Plan for late additions (without overordering)

There’s almost always someone who misses the deadline.

Maybe a new employee joins the company. A last-minute volunteer signs up. Or Uncle Dave decides he’s coming to the family reunion after all.

Ordering a few extra shirts can be smart, especially for events and organizations expecting last-minute additions.

But how many extras should you order?

For a group of 100 people, you might consider an additional 5–10 shirts as a starting point, depending on your budget and how likely your headcount is to change.

That doesn’t mean automatically ordering ten larges.

Look at the sizes you’ve already collected and use that distribution to guide your extras. If you know specific late additions are coming, ask for their sizes before guessing.

It’s also worth discussing quantities with your printer. Bulk screen printing often has price breaks at certain order volumes, meaning a few additional shirts may be more cost-effective than placing a separate order later.

At Charm City Screen Print, we’re happy to help you review your quantities and find an approach that makes sense for your group.

7. Double-check everything before placing your order

You’ve collected everyone’s responses, selected your shirts, and finalized your design. You’re almost there!

Before submitting your group apparel order, take a few minutes to review the details.

Here’s a quick checklist:

• Confirm the exact shirt brand, style, and color.
• Verify sizes against the manufacturer’s chart.
• Check totals for each style and size.
• Include youth and extended sizes where needed.
• Decide how many extra shirts to order.
• Confirm your artwork and print locations.
• Double-check your budget and delivery deadline.

For even more order-planning tips, take a look at our checklist for getting custom shirts printed.

Catching a small mistake before production is always easier than discovering it after 100 shirts have been printed.

Make your next group apparel order a breeze

Whether you’re ordering shirts for employees, outfitting a Baltimore sports team, or organizing merchandise for a big event, figuring out how to order custom shirts for a group starts with getting the sizes right.

The secret isn’t predicting what everyone wears. It’s choosing the right garment, making size collection easy, and working with a printer who can help you sort out the details.

At Charm City Screen Print, we help businesses, schools, teams, and organizations throughout Maryland and beyond create custom apparel people actually want to wear.

Ready to get your group looking great? Contact us for a free custom apparel quote, and let’s make your next order a success!